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100-51-6

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100-51-6 Usage

Chemical Description

Different sources of media describe the Chemical Description of 100-51-6 differently. You can refer to the following data:
1. Benzyl alcohol is a colorless liquid that is used as a solvent and a fragrance ingredient.
2. Benzyl alcohol is an organic compound with the formula C6H5CH2OH.

Overviews

Phenylcarbinol is also known as benzyl alcohol. Its chemical formula is C6H5CH2OH and its density is 1.045 g/mL at 25 ° C (lit). Benzylalcohol is one of the simplest fatty alcohol containing phenyl. It can be seen as benzene substituted by hydroxymethyl, or methyl alcohol substituted by phenyl. It is a colorless transparent sticky liquid with faint aroma. Sometimes benzyl alcohol is placed for a long time, it will smells like bitter almond flavor because of oxidation. Polarity, low toxicity and low steam, so it is used as alcohol solvent. It is combustible, and slightly soluble in water (about 25ml of water soluble 1 gram of benzyl alcohol). It is miscible with ethanol, ethyl ether, benzene, chloroform and other organic solvents.Benzyl alcohol mainly exists in the form of free or ester in essential oil, such as jasmine oil, ylang-ylang oil, jasmine oil, hyacinth oil, sesame oil, hyacinths balsam, peru balsam and tolu balsam, which all contain this ingredient.Benzyl alcohol should not be stored for a long time. It can be slowly oxidized to benzaldehyde and anisole in the air.Therefore benzyl alcohol products often smell like almond aroma with characteristic of benzaldehyde. In addition, benzyl alcohol is also easily oxidized to benzoic acid by many kinds of antioxidants such as nitric acid.

Chemical Properties

Different sources of media describe the Chemical Properties of 100-51-6 differently. You can refer to the following data:
1. Benzyl alcohol has a characteristic pleasant, fruity odor and a slightly pungent, sweet taste; the note tends to become similar to that of benzyl aldehyde on aging. Slightly soluble in water, and miscible with alcohol, ether, chloroform and so on.
2. Benzyl alcohol occurs in many essential oils and foods. It is a colorless liquid with a weak, slightly sweet odor. Benzyl alcohol can be oxidized to benzaldehyde, for example, with nitric acid. Dehydrogenation over a copper–magnesium oxide–pumice catalyst also leads to the aldehyde. Esterification of benzyl alcohol results in a number of important fragrance and flavor materials. Diphenylmethane is prepared by a Friedel–Crafts reaction of benzyl alcohol and benzene with aluminum chloride or concentrated sulfuric acid. By heating benzyl alcohol in the presence of strong acids or strong bases, dibenzyl ether is formed.

Uses

Different sources of media describe the Uses of 100-51-6 differently. You can refer to the following data:
1. Benzyl alcohol is a colorless clear oily liquid; its odor type is floral and its odor at 100% is described as 'floral rose phenolic balsamic'.Benzyl alcohol is used in cosmetics as afragrance component, preservative, solvent and diluting agent for perfumes and flavors, and viscosity-decreasing agent. It is used as a solvent for surface-coating materials, cellulose esters and ethers, alkyd resins,acrylic resins, fats, dyestuffs,casein (when hot), gelatin, shellac and waxes. It is added in small amounts to surface-coating materials to improve their flow and gloss. In the textile industry, benzyl alcohol is used as anauxiliary in the dyeing of wool, polyamides, and polyesters. In pharmacy it is used as a local anesthetic ingredient in over-the-counter anorectal, oral healthcare and topical analgesic drug products and, because of its antimicrobial effect, as an ingredient of ointments and other preparations (U.S. National Library of Medicine).Benzyl alcohol is also a starting material for the preparation of numerous benzyl esters that are used as odorants, flavors, stabilizers for volatile perfumes, and plasticizers and is also employed in the extractive distillation of m- and p-xylenes and m- and p-cresols. Other uses include or have included heat-sealing of polyethylene films,in color photography as a development accelerator and in microscopy as embedding material (U.S.National Library of Medicine).
2. Esters of benzyl alcohol are used in makingperfume, soap, flavoring, lotion, and ointment.It finds application in color photography;the pharmaceuticals industry, cosmetics,and leather dyeing; and as an insect repellent.It occurs in natural products such as oils ofjasmine and castoreum.
3. Benzyl alcohol is widely used as a solvent for the dielectrophoretic reconfiguration of nanowires, inks, paints, lacquers and epoxy resin coatings and as a precursor to a variety of esters used in soaps, perfumes and flavoring. It is employed as a local anesthetic which reduces the pain associated with lidocaine injection. It has a various applications in baby products, bath products, soaps and detergents, eye makeup, blushers, cleansing products, make up products as well as hair, nail and skin care products.
4. benzyl alcohol is a preservative against bacteria, used in concentrations of 1 to 3 percent. It can cause skin irritation.

Production Method

1.Benzyl chloride with potassium or sodium is heated for a long timg, and hydrolyzes to yield benzyl alcohol. 2.Benzaldehyde in methanol and sodium hydroxide solution react to benzyl alcohol at 65~75 ℃. The product has high purity. 3.Using benzyl chloride as raw materials, it is heated and hydrolyzes to yield benzyl alcohol in the presence of the sodium catalyst. Specification of spices benzyl alcohol(QB792-81): the relative density of 1.041-1.046; refractive index of 1.538-1.541; boiling range 203-206℃ and distillate volume more than 95%; dissolving completely in 30 volumes of distilled water; containing more than 98 percent of alcohol; chlorine test (NF) as the side reaction. Raw material consumption quota: benzyl chloride 1600kg/t; soda ash 1000kg/t. 4.Benzyl alcohol exists naturally in orange flower, ylang-ylang, jasmine, gardenia, acacia, lilac and hyacinth. Benzyl chloride or benzaldehyde is used as raw materials to prepare benzyl alcohol in the industry. 5.Add chlorobenzyl to 12% sodium carbonate solution, heat to 93 ℃ and stir for 5h. Then warm the mixture to 101~103℃ and react for 10h. After the reaction, cool it to the room temperature, and add salt to saturation. After still standing for stratification, take the upper liquid and get crude products through pressure distillation. Then refine to gain the target products. The yield is 70%~72%. C6H5CH2Cl+H2O[Na2CO3]→C6H5CH2OH+NaCl+CO2↑ In the presence of sodium hydroxide, formaldehyde and benzaldehyde react to produce benzyl alcohol by disproportionation reaction. C6H5CHO+HCHO[NaOH]→C6h5CH2OH+HCOONa

Description

Benzyl alcohol is a component catalyst for epoxy resins. It is also contained in the color developer C-22.

Physical properties

Colorless, hygroscopic, air sensitive liquid with a faint, pleasant, aromatic odor. Odor threshold concentration in water is 10 ppm (Buttery et al., 1988).

Occurrence

The free alcohol is often present in several essential oils and extracts of jasmine, tobacco, tea, neroli, copaiba, Acacia farnesiana Willd., Acacia cavenia Hook. and Arn., Robinia pseudacacia, ylang-ylang, Pandanus odoratissimus, Michelia champaca, Prunus laurocerasus, tuberose, orris, castoreum, violet leaves, clove buds and others. Also found in fresh apple, apricot, mandarin peel oil, high bush blueberry, raspberry, strawberry fruit, American cranberry and cooked asparagus.

Definition

Different sources of media describe the Definition of 100-51-6 differently. You can refer to the following data:
1. ChEBI: Benzyl alcohol is an aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent. It has a role as a solvent, a metabolite, an antioxidant and a fragrance.
2. An aromatic primary alcohol. Phenylmethanol is synthesized by Cannizzaro’s reaction, which involves the simultaneous oxidation and reduction of benzenecarbaldehyde (benzaldehyde) by refluxing in an aqueous solution of sodium hydroxide: 2C6H5CHO → C6H5CH2OH + C6H5COOH Phenylmethanol undergoes the reactions characteristic of alcohols, especially those in which the formation of a stable carbonium ion as an intermediate (C6H5CH2 +) enhances the reaction. Substitution onto the benzene ring is also possible; the –CH2OH group directs into the 2- or 4-position by the donation of electrons to the ring.

Preparation

Benzyl alcohol is prepared commercially by the distillation of benzyl chloride with potassium or sodium carbonate. It may also be prepared by the Cannizzaro reaction of benzaldehyde and potassium hydroxide.

World Health Organization (WHO)

Benzyl alcohol has been used as an antimicrobial agent in pharmaceutical preparations for many years. Parenteral administration of preparations containing 0.9% benzyl alcohol resulted in the death of 16 neonates in the USA in the early 1980s. Many countries subsequently warned against using such preparations in neonates. This decision is not applicable to the use of benzyl alcohol as a preservative in other circumstances or to its use in topical preparations and no country has placed a total ban on the compound.

Aroma threshold values

Detection: 1.2 to 1000 ppb; also 10 to 1000 ppm.

Taste threshold values

Taste characteristics at 50 ppm: chemical, fruity with balsamic nuances.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 36, p. 3628, 1988 DOI: 10.1248/cpb.36.3628Journal of the American Chemical Society, 107, p. 2428, 1985 DOI: 10.1021/ja00294a038Tetrahedron Letters, 35, p. 1515, 1994 DOI: 10.1016/S0040-4039(00)76746-3

General Description

A clear colorless liquid with a pleasant odor. Slightly denser than water. Flash point 194°F. Boiling point 401°F. Contact may irritate skin, eyes, and mucous membranes. May be slightly toxic by ingestion. Used to make other chemicals.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

Attacks plastics. [Handling Chemicals Safely 1980. p. 236]. Acetyl bromide reacts violently with alcohols or water [Merck 11th ed. 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: an explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid [Chem. Eng. News 45(43):73 1967; J, Org. Chem. 28:1893 1963]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites [NFPA 491 M 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].

Hazard

Highly toxic.

Health Hazard

Benzyl alcohol is a low acute toxicant witha mild irritation effect on the skin. Theirritation in 24 hours from the pure compoundwas mild on rabbit skin and moderateon pig skin. A dose of 750 μg producedsevere eye irritation in rabbits. The toxicityof benzyl alcohol is of low order,the effects varying with the species. Oralintake of high concentrations of this compoundproduced behavioral effects in rats.The symptoms progressed from somnolenceand excitement to coma. Intravenous administrationin dogs produced ataxia, dyspnea,diarrhea, and hypermotility in the animals.Adult and neonatal mice treated withbenzyl alcohol exhibited behavioral change,including sedation, dyspnea, and loss ofmotor function. Pretreatment with pyrazoleincreased the toxicity of benzyl alcohol. Withdisulfiram the toxicity remained unchanged.The study indicated that the acute toxicitywas due to the alcohol itself andnot to bezaldehyde, its primary metabolite(McCloskey et al. 1986).

Fire Hazard

Benzyl alcohol is combustible.

Flammability and Explosibility

Nonflammable

Pharmaceutical Applications

Benzyl alcohol is an antimicrobial preservative used in cosmetics, foods, and a wide range of pharmaceutical formulations, including oral and parenteral preparations, at concentrations up to 2.0% v/v. The typical concentration used is 1% v/v, and it has been reported to be used in protein, peptide and small molecule products, although its frequency of use has fallen from 48 products in 1996, 30 products in 2001, to 15 products in 2006. In cosmetics, concentrations up to 3.0% v/v may be used as a preservative. Concentrations of 5% v/v or more are employed as a solubilizer, while a 10% v/v solution is used as a disinfectant. Benzyl alcohol 10% v/v solutions also have some local anesthetic properties, which are exploited in some parenterals, cough products, ophthalmic solutions, ointments, and dermatological aerosol sprays. Although widely used as an antimicrobial preservative, benzyl alcohol has been associated with some fatal adverse reactions when administered to neonates. It is now recommended that parenteral products preserved with benzyl alcohol, or other antimicrobial preservatives, should not be used in newborn infants if at all possible.

Contact allergens

Benzyl alcohol is mainly a preservative, mostly used in topical antimycotic or corticosteroid ointments. It is also a component catalyst for epoxy resins and is contained in the color developer C-22. As a fragrance allergen, it has to be mentioned by name in cosmetics within the EU.

Safety

Benzyl alcohol is used in a wide variety of pharmaceutical formulations. It is metabolized to benzoic acid, which is further metabolized in the liver by conjugation with glycine to form hippuric acid, which is excreted in the urine. Ingestion or inhalation of benzyl alcohol may cause headache, vertigo, nausea, vomiting, and diarrhea. Overexposure may result in CNS depression and respiratory failure. However, the concentrations of benzyl alcohol normally employed as a preservative are not associated with such adverse effects. Reports of adverse reactions to benzyl alcohol used as an excipient include toxicity following intravenous administration; neurotoxicity in patients administered benzyl alcohol in intrathecal preparations; hypersensitivity, although relatively rare; and a fatal toxic syndrome in premature infants. The fatal toxic syndrome in low-birth-weight neonates, which includes symptoms of metabolic acidosis and respiratory depression, was attributed to the use of benzyl alcohol as a preservative in solutions used to flush umbilical catheters. As a result of this, the FDA has recommended that benzyl alcohol should not be used in such flushing solutions and has advised against the use of medicines containing preservatives in the newborn. The WHO has set the estimated acceptable daily intake of the benzyl/benzoic moiety at up to 5 mg/kg body-weight daily. LD50 (mouse, IV): 0.32 g/kg LD50 (mouse, oral): 1.36 g/kg LD50 (rat, IP): 0.4 g/kg LD50 (rat, IV): 0.05 g/kg LD50 (rat, oral): 1.23 g/kg

Synthesis

By saponification of the ester present in Tolu and Pery balsams; synthetically, it is obtained from benzyl chloride by the action of sodium or potassium carbonate.

Carcinogenicity

In an NTP study, F344 rats were dosed by oral gavage with 0, 200, and 400 mg/kg, 5 days/ week for 2 years. Benzyl alcohol had no effect on the survival of male rats; female rats had reduced survival, and many of the early deaths were considered related to the gavage procedure. There were no treatment-related effects on nonneoplastic or neoplastic lesions in either sex treated with benzyl alcohol. It was concluded that under the conditions of the study, there was no evidence of carcinogenic activity . In the same NTP study, B6C3F1 mice were dosed by oral gavage with 0, 100, and 200 mg/kg, 5 days/week for 2 years. No effects on survival or body weight gain were observed. There were no treatment-related effects on nonneoplastic or neoplastic lesions in either sex. It was concluded that under the conditions of the study, there was no evidence of carcinogenic activity.

Source

Benzyl alcohol naturally occurs in tea (900 ppm), daffodils (165–330 ppm), hyacinths (64–920 ppm), jasmine (120–228 ppm) rosemary (7–32 ppm), hyssop (0.1–30 ppm), tangerines (1–2 ppm), blueberries (0.01–0.08 ppm in fruit juice), ylang-ylang, colocynth, licorice, roselle, tomatoes, spearmint, sweet basil, apricots, tuberose (Duke, 1992), and small-flowered oregano shoots (2 ppm) (Baser et al., 1991). Also identified among 139 volatile compounds identified in cantaloupe (Cucumis melo var. reticulates cv. Sol Real) using an automated rapid headspace solid phase microextraction method (Beaulieu and Grimm, 2001).

Environmental fate

Biological. Heukelekian and Rand (1955) reported a 5-d BOD value of 1.55 g/g which is 61.5% of the ThOD value of 2.52 g/g. Chemical/Physical. Slowly oxidizes in air to benzaldehyde (Huntress and Mulliken, 1941). Benzyl alcohol will not hydrolyze because it has no hydrolyzable functional group (Kollig, 1993).

Metabolism

Esters of benzyl alcohol are rapidly hydrolysed in vivo to benzyl alcohol, which is then oxidized . The animal organism readily oxidizes benzyl alcohol to benzoic acid, which after conjugation with glycine is rapidly eliminated as hippuric acid in the urine.Benzyl alcohol is oxidised by alcohol dehydrogenase (AlcDH), a cytoplasmic enzyme present mainly in the liver, but also in the intestine and kidney. This reaction is saturable. The benzaldehyde formed is oxidised by aldehyde dehydrogenases (AldDH), cytoplasmic and mitochondrial enzymes mainly present in the liver, but also in the intestine and numerous organs.

storage

Benzyl alcohol oxidizes slowly in air to benzaldehyde and benzoic acid; it does not react with water. Aqueous solutions may be sterilized by filtration or autoclaving; some solutions may generate benzaldehyde during autoclaving. Benzyl alcohol may be stored in metal or glass containers. Plastic containers should not be used; exceptions to this include polypropylene containers or vessels coated with inert fluorinated polymers such as Teflon. Benzyl alcohol should be stored in an airtight container, protected from light, in a cool, dry place.

Purification Methods

It is usually purified by careful fractional distillation under reduced pressure in the absence of air. Benzaldehyde, if present, can be detected by UV absorption at 283nm. It has also been purified by shaking with aqueous KOH and extracting with peroxide-free diethyl ether. After washing with water, the extract is treated with saturated NaHS solution, filtered, washed, dried with CaO and distilled under reduced pressure [Mathews J Am Chem Soc 48 562 1926]. Peroxy compounds can be removed by shaking with a solution of Fe2+ followed by washing the alcohol layer with distilled water and fractionally distilling it. [Beilstein 6 IV 2222.]

Toxicity evaluation

Due to an abundance of useful applications across society, from industrial production to consumer products, benzyl alcohol is present in the environment and is steadily released through commercial and household waste streams. Benzyl alcohol was an early object of chemists striving for greener synthetic approaches involving mixed catalysts for oxidation. It is released into the atmosphere entirely as a vapor due to its high vapor pressure, where it is lost by degradation involving reaction with hydroxyl radicals at a half-life of about 2 days. Benzyl alcohol is expected to have quite high mobility based upon its soil to water partition coefficient, and a projected soil half-life of about 13 days.

Incompatibilities

Benzyl alcohol is incompatible with oxidizing agents and strong acids. It can also accelerate the autoxidation of fats. Although antimicrobial activity is reduced in the presence of nonionic surfactants, such as polysorbate 80, the reduction is less than is the case with hydroxybenzoate esters or quaternary ammonium compounds. Benzyl alcohol is incompatible with methylcellulose and is only slowly sorbed by closures composed of natural rubber, neoprene, and butyl rubber closures, the resistance of which can be enhanced by coating with fluorinated polymers. However, a 2% v/v aqueous solution in a polyethylene container, stored at 208℃, may lose up to 15% of its benzyl alcohol content in 13 weeks. Losses to polyvinyl chloride and polypropylene containers under similar conditions are usually negligible. Benzyl alcohol can damage polystyrene syringes by extracting some soluble components

Regulatory Status

Included in the FDA Inactive Ingredients Database (dental injections, oral capsules, solutions and tablets, topical, and vaginal preparations). Included in parenteral and nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

Check Digit Verification of cas no

The CAS Registry Mumber 100-51-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 100-51:
(5*1)+(4*0)+(3*0)+(2*5)+(1*1)=16
16 % 10 = 6
So 100-51-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2

100-51-6 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (L03292)  Benzyl alcohol, 99%   

  • 100-51-6

  • 250g

  • 261.0CNY

  • Detail
  • Alfa Aesar

  • (L03292)  Benzyl alcohol, 99%   

  • 100-51-6

  • 1000g

  • 599.0CNY

  • Detail
  • Alfa Aesar

  • (L03292)  Benzyl alcohol, 99%   

  • 100-51-6

  • 2500g

  • 676.0CNY

  • Detail
  • Riedel-de Haën

  • (80708)  Benzylalcohol  CHROMASOLV®, GC-Headspace tested, ≥99.9% (GC)

  • 100-51-6

  • 80708-1L

  • 2,824.38CNY

  • Detail
  • Sigma-Aldrich

  • (39971)  Benzylalcohol  certified reference material, TraceCERT®

  • 100-51-6

  • 39971-100MG

  • 1,054.17CNY

  • Detail
  • Sigma-Aldrich

  • (305197)  Benzylalcohol  anhydrous, 99.8%

  • 100-51-6

  • 305197-100ML

  • 1,326.78CNY

  • Detail
  • Sigma-Aldrich

  • (305197)  Benzylalcohol  anhydrous, 99.8%

  • 100-51-6

  • 305197-1L

  • 2,566.98CNY

  • Detail
  • Sigma-Aldrich

  • (305197)  Benzylalcohol  anhydrous, 99.8%

  • 100-51-6

  • 305197-2L

  • 3,658.59CNY

  • Detail
  • Sigma-Aldrich

  • (305197)  Benzylalcohol  anhydrous, 99.8%

  • 100-51-6

  • 305197-6X1L

  • 12,893.40CNY

  • Detail
  • Sigma-Aldrich

  • (08421)  Benzylalcohol  analytical standard

  • 100-51-6

  • 08421-5ML-F

  • 556.92CNY

  • Detail
  • Sigma-Aldrich

  • (08421)  Benzylalcohol  analytical standard

  • 100-51-6

  • 08421-25ML-F

  • 2,163.33CNY

  • Detail
  • Vetec

  • (V900264)  Benzylalcohol  Vetec reagent grade, 98%

  • 100-51-6

  • V900264-500ML

  • 88.92CNY

  • Detail

100-51-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name benzyl alcohol

1.2 Other means of identification

Product number -
Other names Benzyl alcohol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:100-51-6 SDS

100-51-6Synthetic route

benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.5h;100%
With RuCl2(2-(diphenylphosphino)-N-(thiophen-2-ylmethyl)ethanamine)PPh3; hydrogen; sodium methylate In toluene at 100℃; under 37503.8 Torr; for 16h; Autoclave;100%
With dichloro(benzene)ruthenium(II) dimer; 2-((di-p-tolylphosphino)methyl)-1-methyl-1H-imidazole; potassium tert-butylate; hydrogen In tetrahydrofuran at 100℃; under 37503.8 Torr; for 4.5h;99%
benzaldehyde
100-52-7

benzaldehyde

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With Triethoxysilane; potassium fluoride for 36h; Product distribution;100%
With n-butyllithium; 1-methoxycyclohexa-1,4-diene In tetrahydrofuran; Petroleum ether for 5h; Product distribution; Ambient temperature;100%
With sodium tetrahydroborate In methanol; dichloromethane at 22℃; for 0.00166667h; also in other alcohols, also at other temperatures, also the reduction time required for 50percent reduction;100%
benzoyl chloride
98-88-4

benzoyl chloride

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; silica gel In hexane at 25℃; for 3h;100%
With diisopropoxytitanium(III) tetrahydroborate In dichloromethane at -20℃; for 0.133333h;100%
With trihexyl(tetradecyl)phosphonium decanoate*BH3 at 20℃; Product distribution / selectivity;99%
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With C32H34BrN5ORu; potassium tert-butylate; hydrogen In tetrahydrofuran at 70℃; under 37503.8 Torr; for 4h; Reagent/catalyst;100%
With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium tert-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox; Autoclave;100%
With C32H32Cl2N2P2Ru; hydrogen; sodium methylate In para-xylene; toluene at 5 - 100℃; under 37503.8 Torr; for 4h; Reagent/catalyst; Glovebox;100%
tetrahydro-2-(benzyloxy)-2H-pyran
1927-62-4

tetrahydro-2-(benzyloxy)-2H-pyran

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With dinitrogen tetraoxide In dichloromethane at -10℃; deprotection;100%
poly(4-vinylpyridinium) p-toluenesulfonate In tetrahydrofuran; ethanol at 75℃; for 30h; Hydrolysis;99%
With C24H20O3; toluene-4-sulfonic acid In tetrahydrofuran; methanol at 20℃; for 1h;99%
benzyloxy-trimethylsilane
14642-79-6

benzyloxy-trimethylsilane

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With dinitrogen tetraoxide In dichloromethane at -10℃; deprotection;100%
With water; 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane at 20℃; for 0.25h;100%
montmorillonite K-10 for 0.0166667h; Solid phase reaction; desilylation; microwave irradiation;99%
O-Alloc benzyl alcohol
22768-01-0

O-Alloc benzyl alcohol

A

propene
187737-37-7

propene

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) In benzene at 5℃;A n/a
B 100%
benzyl formate
104-57-4

benzyl formate

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In o-xylene at 80℃; for 24h; Inert atmosphere;100%
Stage #1: benzyl formate With phenylsilane; C74H74Mn2N6P4 at 25℃; for 0.5h; Glovebox; Inert atmosphere;
Stage #2: With sodium hydroxide In water at 25℃; for 2h; Glovebox; Inert atmosphere;
99%
Stage #1: benzyl formate With phenylsilane; (Ph2PPrPDI)Mn at 25℃; for 0.25h; Glovebox; Inert atmosphere;
Stage #2: With sodium hydroxide In water at 25℃; for 2h; Catalytic behavior; Reagent/catalyst; Glovebox;
88%
benzoic acid benzyl ester
120-51-4

benzoic acid benzyl ester

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium tert-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox; Autoclave;100%
With dichloro(benzene)ruthenium(II) dimer; 2-((di-p-tolylphosphino)methyl)-1-methyl-1H-imidazole; potassium tert-butylate; hydrogen In tetrahydrofuran at 100℃; under 37503.8 Torr; for 2h;99%
With C66H102N4OP2Ru; hydrogen In toluene at 105℃; under 22502.3 Torr; for 20h; Inert atmosphere; Glovebox;99%
benzyl (1-chloroethyl) carbonate
99464-81-0

benzyl (1-chloroethyl) carbonate

ammonium thiocyanate

ammonium thiocyanate

A

benzyl 1-thiocyanoethylcarbonate
117972-00-6

benzyl 1-thiocyanoethylcarbonate

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With tetrabutyl phosphonium bromide In acetone for 18.5h; Heating;A 100%
B 18%
benzyl bromide
100-39-0

benzyl bromide

2-(trimethylsilyl)ethyl benzeneselenenate
133957-60-5

2-(trimethylsilyl)ethyl benzeneselenenate

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 7h; Ambient temperature;100%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 7h; Product distribution; Ambient temperature; other alkyl halides, different reation times;100%
benzyl 2-(2-hydroxypropyl)phenyl sulfone
111396-78-2

benzyl 2-(2-hydroxypropyl)phenyl sulfone

A

3-methyl-1-oxobenzo-2,1-oxathiane
111396-79-3

3-methyl-1-oxobenzo-2,1-oxathiane

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 1h;A 100%
B 100%
benzenesulphonylacetic acid benzyl ester
152757-22-7

benzenesulphonylacetic acid benzyl ester

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With ethanol; magnesium; mercury dichloride In tetrahydrofuran for 2h; Ambient temperature;100%
2-iodobenzyl alcohol
5159-41-1

2-iodobenzyl alcohol

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); hypophosphorous acid; sodium hydrogencarbonate In ethanol for 5h; Heating;100%
With tri(2-furyl)germane; triethyl borane In tetrahydrofuran at 20℃; for 1.5h; Reduction;93%
With tri(2-furyl)germane; triethyl borane In tetrahydrofuran; hexane at 20℃; for 1.5h;93%
With isopropyl alcohol at 20℃; for 12h; UV-irradiation; chemoselective reaction;86%
With potassium phosphate; palladium diacetate; hydrazine hydrate In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 8h; Green chemistry;78%
benzyl trifluoroacetate
351-70-2

benzyl trifluoroacetate

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With silica gel; triethylamine In diethyl ether; Petroleum ether Substitution; Detrifluoroacetylation;100%
methanol
67-56-1

methanol

Benzyl 3-phenylpropionate
22767-96-0

Benzyl 3-phenylpropionate

A

3-phenylpropanoic acid methyl ester
103-25-3

3-phenylpropanoic acid methyl ester

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A 100%
B n/a
ethanol
64-17-5

ethanol

Benzyl 3-phenylpropionate
22767-96-0

Benzyl 3-phenylpropionate

A

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A 100%
B n/a
Benzyl 3-phenylpropionate
22767-96-0

Benzyl 3-phenylpropionate

allyl alcohol
107-18-6

allyl alcohol

A

allyl 3-phenylpropionate
15814-45-6

allyl 3-phenylpropionate

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A 100%
B n/a
(2R,3S)-1-chloro-3-dibenzylamino-4-phenyl-2-butanol sulfuric acid salt
934971-01-4

(2R,3S)-1-chloro-3-dibenzylamino-4-phenyl-2-butanol sulfuric acid salt

A

(2R,3S)-1-chloro-3-amino-4-phenyl-2-butanol sulfuric acid salt
934971-02-5

(2R,3S)-1-chloro-3-amino-4-phenyl-2-butanol sulfuric acid salt

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With hydrogen; palladium hydroxide/carbon In methanol at 40℃; for 3h;A 100%
B n/a
Li(1+)*ReMn(CO)9(CHO)(1-)=Li(ReMn(CO)9(CHO))
85283-42-7

Li(1+)*ReMn(CO)9(CHO)(1-)=Li(ReMn(CO)9(CHO))

benzaldehyde
100-52-7

benzaldehyde

A

decacarbonylmanganeserhenium
14693-30-2

decacarbonylmanganeserhenium

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
In tetrahydrofuran under N2, benzaldehyde was added to soln. of Re-Mn-complex in THF at -78°C, warmed to -30°C, 5 min, quenched with aq. THF;A 58%
B 100%
Li[cis-Re2(CO)9(CHO)]*tetrahydrofuran

Li[cis-Re2(CO)9(CHO)]*tetrahydrofuran

benzaldehyde
100-52-7

benzaldehyde

A

decacarbonyldirhenium(0)
14285-68-8

decacarbonyldirhenium(0)

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With tetradecane In tetrahydrofuran under N2, 1.13 equiv of benzaldehyde in THF was added to soln. of Re-complex in THF, stirred for 1 h, water was added , extd. with ether, driedover Na2SO4, 1 equiv of tetradecane standard was added; solvent removed, dissolved in min. ether, hexane added, placed in freezer overnight, crystd., filtered, vac. dried;A 100%
B 74%
C28H28BO4(1-)*Na(1+)

C28H28BO4(1-)*Na(1+)

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With water100%
tert-butyldimethyl(phenoxy)silane
18052-27-2

tert-butyldimethyl(phenoxy)silane

(benzyloxy)(tert-butyl)dimethylsilane
53172-91-1

(benzyloxy)(tert-butyl)dimethylsilane

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With 1,11-bis(3-methyl-3H-imidazolium-1-yl)-3,6,9-trioxaundecane di(methanesulfonate) In methanol at 20℃; for 1.41667h;100%
benzoic acid
65-85-0

benzoic acid

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With diisobutylaluminum borohydride In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;99%
Stage #1: benzoic acid With borane-2-methyltetrahydrofuran complex In 2-methyltetrahydrofuran at 0 - 20℃; for 3h;
Stage #2: With water In 2-methyltetrahydrofuran Product distribution / selectivity;
97.1%
With [Zn(BH4)2(py)] In tetrahydrofuran for 1.5h; Heating;96%
propyl benzoate
2315-68-6

propyl benzoate

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With C32H36ClNO2P2Ru; potassium tert-butylate; hydrogen In tetrahydrofuran at 120℃; under 38002.6 Torr; for 12h; Autoclave; Green chemistry;99%
With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 38002.6 - 76005.1 Torr; for 15h; Glovebox; Autoclave;95%
With lithium aluminium tetrahydride In diethyl ether for 1h; Heating; Yield given;
Benzyl acetate
140-11-4

Benzyl acetate

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With [Ru(2-(methylthio)-N-[(pyridin-2-yl)methyl]ethan-1-amine)(triphenylphosphine)Cl2]; potassium tert-butylate; hydrogen In toluene at 80℃; under 30003 Torr; for 3h;99%
With methanol; sodium methylate at 60℃; Reagent/catalyst;99%
With Ximenia american In water at 30℃; for 72h; pH=5; Enzymatic reaction;98%
(benzyloxy)(tert-butyl)dimethylsilane
53172-91-1

(benzyloxy)(tert-butyl)dimethylsilane

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With C24H20O3; tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h;99%
With water; aluminium In hexane for 15h; Ambient temperature;98%
With polymer-supported dicyanoketene acetal; water In acetonitrile at 20℃; for 24h; Hydrolysis;98%
N,N-diisopropyl benzamide
20383-28-2

N,N-diisopropyl benzamide

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With n-butyllithium; borane-THF; 2,3-dihydropyrrole at 65℃;99%
With LiPyrrBH3 In tetrahydrofuran at 25℃; for 2h;99%
benzyl tert-butyldiphenylsilyl ether
139706-45-9

benzyl tert-butyldiphenylsilyl ether

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With potassium fluoride; Tetraethylene glycol at 80℃; for 3.5h;99%
With hafnium tetrakis(trifluoromethanesulfonate) In methanol at 20℃; for 3h; chemoselective reaction;97%
With hafnium tetrakis(trifluoromethanesulfonate) In methanol at 20℃; for 3h; chemoselective reaction;97%
benzoic acid phenyl ester
93-99-2

benzoic acid phenyl ester

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With dimethylsulfide borane complex In 2-methyltetrahydrofuran at 90℃; under 7500.75 Torr; for 0.333333h; Inert atmosphere; Flow reactor; chemoselective reaction;99%
With sodium tetrahydroborate; C36H30F6N10Ni4O10(2+)*2C2F3O2(1-); zinc(II) chloride In tetrahydrofuran at 45℃; for 12h;90%
With methylsilane; potassium tert-butylate In tetrahydrofuran at 70℃; for 72h; Reagent/catalyst; Time; Inert atmosphere; Schlenk technique; Glovebox; chemoselective reaction;76%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

benzyl alcohol
100-51-6

benzyl alcohol

tetrahydro-2-(benzyloxy)-2H-pyran
1927-62-4

tetrahydro-2-(benzyloxy)-2H-pyran

Conditions
ConditionsYield
zeolite HSZ-360 In neat (no solvent) at 25℃; for 5h;100%
With high p-toluenesulfonate content diphenylamine and terephthalaldehyde resin In acetonitrile at 20℃; for 1h;100%
With monoaluminum phosphate for 0.25h; Product distribution; Heating; other catalyst: AlPO4-Al2O3, other alcohols and phenols;99%
2-aminopyridine
504-29-0

2-aminopyridine

benzyl alcohol
100-51-6

benzyl alcohol

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With dichloro-[1,3-bis(4-tert-butylbenzyl)perhydrobenzimidazol-2-ylidene](p-cymene)ruthenium(II); potassium tert-butylate at 120℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Sealed tube;100%
With potassium tert-butylate; copper diacetate In 1,4-dioxane at 130℃; for 24h;99%
With potassium tert-butylate; copper diacetate In 1,4-dioxane at 130℃; for 24h; Inert atmosphere;99%
nicotinic acid
59-67-6

nicotinic acid

benzyl alcohol
100-51-6

benzyl alcohol

benzyl nicotinate
94-44-0

benzyl nicotinate

Conditions
ConditionsYield
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride In dichloromethane for 1h; Ambient temperature;100%
With N,N'-dimethylaminopyridine; di-tert-butyl dicarbonate In nitromethane at 50℃; for 16h;81%
With boric acid; glycerol Entfernen des entstehenden H2O;
phthalic anhydride
85-44-9

phthalic anhydride

benzyl alcohol
100-51-6

benzyl alcohol

o-(benzyloxycarbonyl)benzoic acid
2528-16-7

o-(benzyloxycarbonyl)benzoic acid

Conditions
ConditionsYield
In pyridine; benzene at 100℃; for 2h;100%
With 1-hydro-3-(3-sulfopropyl)-imidazolium 4-methyl-benzenesulfonate at 60℃; Heating;95%
In pyridine; benzene at 100℃; for 2h;84%
acetic anhydride
108-24-7

acetic anhydride

benzyl alcohol
100-51-6

benzyl alcohol

Benzyl acetate
140-11-4

Benzyl acetate

Conditions
ConditionsYield
With iodine for 15h; Ambient temperature;100%
With magnesium(II) perchlorate at 20℃; for 0.25h;100%
With nickel dichloride for 0.116667h; microwave irradiation;100%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

benzyl alcohol
100-51-6

benzyl alcohol

benzyl acetoacetate
5396-89-4

benzyl acetoacetate

Conditions
ConditionsYield
[Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In toluene for 6h; Heating;100%
With rhizopus niveus lipase; Pseudomonas sp. lipoprotein lipase; Candida antarctica lipase B immobilized on acrylic resin; Carica papaya protease In toluene at 40℃; for 48h; Enzymatic reaction;98%
1-chloro-3-hydroxy-1,1,3,3-tetrabutyldistannoxane In toluene for 16h; Heating;96%
benzoyl chloride
98-88-4

benzoyl chloride

benzyl alcohol
100-51-6

benzyl alcohol

benzoic acid benzyl ester
120-51-4

benzoic acid benzyl ester

Conditions
ConditionsYield
With bifunctional polymer In toluene at 20℃; for 6h;100%
Stage #1: benzoyl chloride; benzyl alcohol In dichloromethane at 20℃;
Stage #2: With poly{trans-bicyclo[2.2.1]hept-5-ene-2,3-di(chlorocarbonyl)} In dichloromethane Heating;
95%
With triethylamine94%
4-methoxy-aniline
104-94-9

4-methoxy-aniline

benzyl alcohol
100-51-6

benzyl alcohol

benzyl(4-methoxyphenyl)amine
17377-95-6

benzyl(4-methoxyphenyl)amine

Conditions
ConditionsYield
With chloro(η5-pentamethylcyclopentadienyl)(L-prolinato)iridium(III) In toluene at 95℃; for 24h; Inert atmosphere; Sealed tube;100%
With potassium tert-butylate; copper diacetate In 1,4-dioxane at 130℃; for 48h;99%
With potassium tert-butylate; copper diacetate In 1,4-dioxane at 130℃; for 48h; Inert atmosphere;99%
4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

benzyl alcohol
100-51-6

benzyl alcohol

benzyl 4-nitrobenzoate
14786-27-7

benzyl 4-nitrobenzoate

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 96h; Inert atmosphere;100%
With dmap In dichloromethane at 20℃; for 24h;92%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;82%
acetic acid
64-19-7

acetic acid

benzyl alcohol
100-51-6

benzyl alcohol

Benzyl acetate
140-11-4

Benzyl acetate

Conditions
ConditionsYield
zirconium(IV) oxide In toluene for 1h; Heating; in vapor-phase at 150 deg C;100%
LaY zeolite at 116℃; for 8h; Acetylation;99%
With bismuth(lll) trifluoromethanesulfonate at 20℃; for 0.25h;99%
bromoacetic acid
79-08-3

bromoacetic acid

benzyl alcohol
100-51-6

benzyl alcohol

Benzyl bromoacetate
5437-45-6

Benzyl bromoacetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene at 120℃; for 24h;100%
With toluene-4-sulfonic acid In benzene at 120℃; for 24h; Inert atmosphere;100%
With toluene-4-sulfonic acid In benzene at 120℃; for 24h;100%
cyanoacetic acid
372-09-8

cyanoacetic acid

benzyl alcohol
100-51-6

benzyl alcohol

benzyl 2-cyanoacetate
14447-18-8

benzyl 2-cyanoacetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 1h;100%
With pyridine In acetonitrile 1.) 0 deg C, 1 h, 2.) 25 deg C, 1 h;98%
With sulfuric acid In benzene for 2.5h; Fischer esterification; Heating;93%
acrylonitrile
107-13-1

acrylonitrile

benzyl alcohol
100-51-6

benzyl alcohol

3-benzyloxypropionitrile
6328-48-9

3-benzyloxypropionitrile

Conditions
ConditionsYield
With [μN,κP,κC,κN-{2-(i-Pr2PO),6-(CH2NBn)-(C6H3)}Ni]2 In benzene at 50℃; for 1h;100%
With sodium hydroxide In water at 20℃; for 6h; Michael addition;99%
With sodium hydroxide at 20℃; Michael Addition;97%
trichloroacetonitrile
545-06-2

trichloroacetonitrile

benzyl alcohol
100-51-6

benzyl alcohol

O-benzyl 2,2,2-trichloroacetimidate
81927-55-1

O-benzyl 2,2,2-trichloroacetimidate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In n-heptane at 0℃; for 0.25h; Solvent;100%
With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In dichloromethane; water at -15 - 20℃; for 1.5h;99%
With potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at -15 - 25℃; for 1h;97%
aniline
62-53-3

aniline

benzyl alcohol
100-51-6

benzyl alcohol

N-Benzylaniline
758640-21-0

N-Benzylaniline

Conditions
ConditionsYield
With C25H27ClIrN4O(1+)*Cl(1-); caesium carbonate at 120℃; for 20h;100%
With potassium tert-butylate; copper diacetate In 1,4-dioxane at 130℃; for 48h;99%
With potassium tert-butylate; copper diacetate In 1,4-dioxane at 130℃; for 48h; Inert atmosphere;99%
phenyl chloroformate
1885-14-9

phenyl chloroformate

benzyl alcohol
100-51-6

benzyl alcohol

benzyl phenyl carbonate
28170-07-2

benzyl phenyl carbonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 16h; Inert atmosphere;100%
With pyridine In dichloromethane at 23℃; Cooling with ice; Inert atmosphere;99%
With pyridine; dmap In dichloromethane at 0 - 20℃; for 13.5h;95%
benzoic acid
65-85-0

benzoic acid

benzyl alcohol
100-51-6

benzyl alcohol

benzoic acid benzyl ester
120-51-4

benzoic acid benzyl ester

Conditions
ConditionsYield
With cyanomethylenetributyl-phosphorane In benzene at 100℃; for 24h;100%
With TiO(acac)2 In xylene for 15h; Heating;100%
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 5h;99%
phenylacetyl chloride
103-80-0

phenylacetyl chloride

benzyl alcohol
100-51-6

benzyl alcohol

benzyl 2-phenylacetate
102-16-9

benzyl 2-phenylacetate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;100%
With samarium In acetonitrile at 70℃; for 0.0333333h;92%
With triethylamine In dichloromethane at 20℃; for 12h;70.1%
trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

benzyl alcohol
100-51-6

benzyl alcohol

benzyl trifluoroacetate
351-70-2

benzyl trifluoroacetate

Conditions
ConditionsYield
erbium(III) triflate In acetonitrile at 20℃; for 0.166667h;100%
With erbium(III) chloride for 2h; Heating;99%
In diethyl ether at 0℃; for 2h; Inert atmosphere;95%
citric acid
77-92-9

citric acid

benzyl alcohol
100-51-6

benzyl alcohol

tribenzyl citrate
631-25-4

tribenzyl citrate

Conditions
ConditionsYield
toluene-4-sulfonic acid In toluene for 18h; Heating / reflux;100%
With hydrogenchloride In xylene for 12h; Esterification; Heating;95%
at 160 - 165℃;
With hydrogenchloride; xylene
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

benzyl alcohol
100-51-6

benzyl alcohol

benzoic acid benzyl ester
120-51-4

benzoic acid benzyl ester

Conditions
ConditionsYield
With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea; 4-pyrrolidin-1-ylpyridine In octane for 24h; Reflux;100%
With dilithium tetra(tert-butyl)zincate at 0℃; for 1h; Temperature; Inert atmosphere;100%
With lanthanum(III) isopropoxide; 2-(2-methoxyethoxy)ethyl alcohol In hexane Reflux; chemoselective reaction;97%
isocyanate de chlorosulfonyle
1189-71-5

isocyanate de chlorosulfonyle

benzyl alcohol
100-51-6

benzyl alcohol

benzyl N-chlorosulfonylcarbamate
89979-13-5

benzyl N-chlorosulfonylcarbamate

Conditions
ConditionsYield
In dichloromethane for 1h;100%
In diethyl ether at 23℃; Inert atmosphere; Cooling with ice;97%
In dichloromethane at -10℃; for 1h;69%
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

benzyl alcohol
100-51-6

benzyl alcohol

benzyl diphenylmethyl ether
26059-49-4

benzyl diphenylmethyl ether

Conditions
ConditionsYield
methyltrioxorhenium(VII) for 48h; Ambient temperature;100%
With boron trifluoride diethyl etherate In toluene at 100℃; for 7h; Concentration; Solvent; Time;98%
With trimethylsilyl bromide at 50℃; for 24h; Sealed tube;98%
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

benzyl alcohol
100-51-6

benzyl alcohol

benzyl (Z)-9-octadecenoate
55130-16-0

benzyl (Z)-9-octadecenoate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In water; benzene for 22h; Heating;100%
With porous phenol sulfonic acid-formaldehyde resin In neat (no solvent) at 90℃; for 6h;91%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 2.5h;85%
benzyl alcohol
100-51-6

benzyl alcohol

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

benzyl 4-nitrobenzoate
14786-27-7

benzyl 4-nitrobenzoate

Conditions
ConditionsYield
With [Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In various solvent(s) at 150℃; for 10h;100%
With [bis(acetoxy)iodo]benzene; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 25℃; for 16h; Mitsunobu reaction;100%
Stage #1: 4-nitro-benzoic acid With N-chlorobenzotriazole; triphenylphosphine In dichloromethane for 0.25h; Cooling;
Stage #2: benzyl alcohol With triethylamine In dichloromethane at 20℃; for 0.333333h;
98%
benzyl alcohol
100-51-6

benzyl alcohol

dibenzyl ether
103-50-4

dibenzyl ether

Conditions
ConditionsYield
With copper(ll) bromide at 175℃; for 8h; Reagent/catalyst;100%
With (NH4)2.8H0.9[ε-VMo9.4V2.6O40Bi2]·7.2H2O at 129.84℃; for 3h; Catalytic behavior; Reagent/catalyst;97%
With benzyl bromide In neat (no solvent) at 120℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Sealed tube; Green chemistry;97%
benzyl alcohol
100-51-6

benzyl alcohol

benzyl bromide
100-39-0

benzyl bromide

Conditions
ConditionsYield
With 1,1,1,2,2,2-hexamethyldisilane; pyridinium hydrobromide perbromide In chloroform at 25℃; for 0.5h;100%
With phosphorus tribromide In benzene at 20℃;100%
Stage #1: benzyl alcohol With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane for 0.0833333h;
Stage #2: With potassium bromide In dichloromethane; N,N-dimethyl-formamide for 0.5h;
99%

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Synthesis of benzyl methyl ether from benzyl alcohol and methanol in high-temperature carbonic water was studied in a batch reactor. Benzyl methyl ether formation was not observed by reacting benzyl alcohol with only methanol under supercritical conditions at 573 K. On the other hand, benzyl met...detailed

One-, two- and three-dimensional coordination polymers based on copper paddle-wheel SBUs as selective catalysts for Benzyl alcohol (cas 100-51-6) oxidation07/26/2019

Copper-based coordination polymers, Cu2(μ2-MeCO2)4(DABCO) (1), [Cu(1,4-BDC-Br)(DABCO)0.5]. xDMF.yH2O (2) and Cu(1,4-BDC-OH)(DMF) (3) (1,4-BDC-Br = 2-bromoterephthalate, DABCO = triethylenediamine, 1,4-BDC-OH = 2-hydroxyterephthalate) were solvothermally synthesized. Two polymorphs of 1 (1a and ...detailed

Evaluation of catalytic activity of MeOx/sepiolite in Benzyl alcohol (cas 100-51-6) oxidation07/24/2019

A series of MeOx/sepiolite (Me = Cu, Cr, Mn, Co, Ni) catalysts was prepared through the deposition–precipitation and characterized by means of XRD, EDS, SEM, BET, and H2-TPR. The structural characterization showed a fine distribution of MeOx metal oxides on magnesium silicate nanobars. The sepi...detailed

Preparation andCharacterization of CuCeO2catalytic materials forthe oxidation of Benzyl alcohol (cas 100-51-6) to benzaldehyde in water07/22/2019

A series of CuCeO2catalytic materials, with copper loadings in the 5–20 wt% range, was prepared, characterized and tested in the oxidation of benzyl alcohol to benzaldehyde in batch conditions, at 100 °C employing water as the solvent. Different CeO2and CuCeO2 samples were obtained following h...detailed

Oxidation of Benzyl alcohol (cas 100-51-6) through eco-friendly processes using Fe-doped cryptomelane catalysts07/21/2019

Due to the convenience of catalyst separation and solvent-free conditions, gas-phase oxidation of benzyl alcohol-in particular to-benzaldehyde reaction is more attractive method for industrial applications. In this respect it is environmentally and scientifically important to develop a low cost,...detailed

Formation of PdO on Au–Pd bimetallic catalysts and the effect on Benzyl alcohol (cas 100-51-6) oxidation07/19/2019

A series of catalysts consisting of gold–palladium bimetallic nanoparticles (Au–Pd NPs in the range of 1–6 nm) anchored on foamlike mesoporous silica were used for the aerobic oxidation of benzyl alcohol. A remarkable synergistic effect was observed on these Au–Pd NP catalysts prepared by a ...detailed

100-51-6Relevant articles and documents

Intracrystalline reactivity of layered double hydroxides: Carboxylate alkylations in dry media

Garcia-Ponce, Angel Luis,Prevot, Vanessa,Casal, Blanca,Ruiz-Hitzky, Eduardo

, p. 119 - 121 (2000)

This work concerns the reactivity in dry media conditions, i.e. without solvents, of layered double hydroxide (LDH) solids, containing carboxylate ions in their structure, towards alkyl and benzyl halides. Reaction occurs giving the corresponding esters, with excellent yield and selectivity, and preserving the lamellar arrangement of the pristine solids. The reactions were activated by conventional thermal treatment (100 °C) or by microwave (MW) irradiation.

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Gaylord,Kay

, p. 1574 (1958)

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REDUCTIVE COUPLING OF AROMATIC ALDEHYDES BY OCTACARBONYL DIFERRATE

Ito, Keiji,Nakanishi, Saburo,Otsuji, Yoshio

, p. 1141 - 1144 (1980)

The reaction of aromatic aldehydes with Fe(CO)5 or Fe3(CO)12 in pyridine gives the corresponding 1,2-diaryl-1,2-ethanediols as major products in good yields.A reactive species of this reaction is octacarbonyl diferrate (2-).

Manganese Catalyzed Hydrogenation of Organic Carbonates to Methanol and Alcohols

Kumar, Amit,Janes, Trevor,Espinosa-Jalapa, Noel Angel,Milstein, David

, p. 12076 - 12080 (2018)

The first example of a homogeneous catalyst based on an earth-abundant metal for the hydrogenation of organic carbonates to methanol and alcohols is reported. Based on the mechanistic investigation, which indicates metal-ligand cooperation between the manganese center and the N?H group of the pincer ligand, we propose that the hydrogenation of organic carbonates to methanol occurs via formate and aldehyde intermediates. The reaction offers an indirect route for the conversion of CO2 to methanol, which coupled with the use of an earth abundant catalyst, makes the overall process environmentally benign and sustainable.

Iron-catalyzed hydrosilylation of esters

Bezier, David,Venkanna, Gopaladasu T.,Castro, Luis C. Misal,Zheng, Jianxia,Roisnel, Thierry,Sortais, Jean-Baptiste,Darcel, Christophe

, p. 1879 - 1884 (2012)

The first hydrosilylation of esters catalyzed by a well defined iron complex has been developed. Esters are converted to the corresponding alcohols at 100 °C, under solvent-free conditions and visible light activation. Copyright

A Pd@Zeolite Catalyst for Nitroarene Hydrogenation with High Product Selectivity by Sterically Controlled Adsorption in the Zeolite Micropores

Zhang, Jian,Wang, Liang,Shao, Yi,Wang, Yanqin,Gates, Bruce C.,Xiao, Feng-Shou

, p. 9747 - 9751 (2017)

The adsorption of molecules on metal nanoparticles can be sterically controlled through the use of zeolite crystals, which enhances the product selectivity in hydrogenations of reactants with more than one reducible group. Key to this success was the fixation of Pd nanoparticles inside Beta zeolite crystals to form a defined structure (Pd@Beta). In the hydrogenation of substituted nitroarenes with multiple reducible groups as a model reaction, the Pd@Beta catalyst exhibited superior selectivity for hydrogenation of the nitro group, outperforming both conventional Pd nanoparticles supported on zeolite crystals and a commercial Pd/C catalyst. The extraordinary selectivity of Pd@Beta was attributed to the sterically selective adsorption of the nitroarenes on the Pd nanoparticles controlled by the zeolite micropores, as elucidated by competitive adsorption and adsorbate displacement tests. Importantly, this strategy is general and was extended to the synthesis of selective Pt and Ru catalysts by fixation inside Beta and mordenite zeolites.

Pt/ZrO2: An efficient catalyst for aerobic oxidation of toluene in aqueous solution

Mohammad, Sadiq,Mohammad, Ilyas

, p. 2216 - 2220 (2010)

The heterogeneous oxidation of toluene in aqueous medium has been investigated. Artificially contaminated water with aromatic compound (toluene) was exposed to a simple platinized zirconia (1% Pt/ZrO2) catalyst in the presence of molecular oxyg

Organometallic chemistry sans organometallic reagents: Modulated electron-transfer reactions of sub valent early transition metal salts

Eisch, John J.,Shi, Xian,Alila, Joseph R.,Thiele, Sven

, p. 1175 - 1187 (1997)

The potential of low-valent, early transition-metal reagents as selective reductants in organic chemistry has been foreshadowed by intensive research on the ill-defined and heterogeneous subvalent titanium intermediates generated in the McMurry reaction and its numerous variants. As part of a long-term research effort to develop soluble, well-defined transition-metal reductants of modulated and selective activity toward organic substrates, the THF-soluble reductant, titanium dichloride, has been thoroughly examined, as well as the analogous ZrCl2 and HfCl2 reagents, all of which are readily obtainable by the alkylative reduction of the Group 4 tetrachloride by butyllithium in THF. Noteworthy is that such interactions of MCl4, with butyllithium in hydrocarbon media lead, in contrast, to M(III) or M(IV) halide hydrides. Analogous alkylative reductions in THF applied to VCl4, CrCl3, and MoCl5 have yielded reducing agents similar to those obtained from MCl4 but gradated in their reactivity. Such reductants have proved capable of coupling carbonyl derivatives, benzylic halides, acetylenes and certain olefins in a manner consistent with an oxidative addition involving a two-electron transfer (TET). Such a reaction pathway is consistent with the observed stereochemistry for pinacol formation from ketones and for the reductive dimerization of alkynes. In contrast to the reaction of CrCl3 with two equivalents of butyllithium, which leads to a CrCl intermediate, the interaction of CrCl3 in THF with four equivalents of butyllithium at -78°C yields a reagent of the empirical formulation, LiCrH4 · 2 LiCl · 2 THF, as supported by elemental and gasometric analysis of its protolysis. This hydridic reductant cleaves a wide gamut of o carbon-heteroatom bonds (C-X, C-O, C-S and C-N), towards which the CrCl reductant is unreactive. The type of cleavage and/or coupled products resulting from the action of "LiCrH4" on these substrates is best understood as arising from single-electron transfer (SET). In light of the aforementioned findings, the gradated reducing action noted among TiCl2, ZrCl2, HfCl2 and CrCl, as well as the contrasting reducing behavior between CrCl and LiCrH4, there is no doubt that future research with early transition metals will continue to yield novel reductants of modulated and site-selective reactivity. VCH Verlagsgesellschaft mbH,.

Tailor-Made Ruthenium-Triphos Catalysts for the Selective Homogeneous Hydrogenation of Lactams

Meuresch, Markus,Westhues, Stefan,Leitner, Walter,Klankermayer, Jürgen

, p. 1392 - 1395 (2016)

The development of a tailored tridentate ligand enabled the synthesis of a molecular ruthenium-triphos catalyst, eliminating dimerization as the major deactivation pathway. The novel catalyst design showed strongly increased performance and facilitated the hydrogenation of highly challenging lactam substrates with unprecedented activity and selectivity. Bulky catalysts: A tailored sterically demanding tridentate ligand enabled the synthesis of a novel molecular ruthenium-triphos catalyst, which eliminates dimerization as the major deactivation pathway. The novel catalyst design showed increased performance and facilitated the hydrogenation of highly challenging lactam substrates with unprecedented activity and selectivity.

Highly efficient tetradentate ruthenium catalyst for ester reduction: Especially for hydrogenation of fatty acid esters

Tan, Xuefeng,Wang, Yan,Liu, Yuanhua,Wang, Fangyuan,Shi, Liyang,Lee, Ka-Ho,Lin, Zhenyang,Lv, Hui,Zhang, Xumu

, p. 454 - 457 (2015)

A new tetradentate ruthenium complex has been developed for hydrogenation of esters. The catalysts structure features a pyridinemethanamino group and three tight chelating five-membered rings. The structure character is believed to be responsible for its high stability and high carbonylation-resistant properties. Thus, this catalyst shows outstanding performance in the catalytic hydrogenation of a variety of esters, especially for fatty acid esters, which may be used in practical applications. New insight on designing hydrogenation catalyst for reducing esters to alcohols has been provided through theoretical calculations.

Copper(ii) induced oxidative modification and complexation of a schiff base ligand: Synthesis, crystal structure, catalytic oxidation of aromatic hydrocarbons and DFT calculation

Biswas, Surajit,Dutta, Arpan,Dolai, Malay,Debnath, Mainak,Jana, Atish Dipankar,Ali, Mahammad

, p. 34248 - 34256 (2014)

A mononuclear square planar complex [CuII(Lf)] (1) was synthesized and structurally characterized by single crystal X-ray diffraction studies. Though we have started with the Schiff base H 2La with two -CH2

Palladium-catalyzed hydrodehalogenation of aryl halides using paraformaldehyde as the hydride source: High-throughput screening by paper-based colorimetric iodide sensor

Pyo, Ayoung,Kim, Sudeok,Kumar, Manian Rajesh,Byeun, Aleum,Eom, Min Sik,Han, Min Su,Lee, Sunwoo

, p. 5207 - 5210 (2013)

Paraformaldehyde was employed as a hydride source in the palladium-catalyzed hydrodehalogenation of aryl iodides and bromides. High throughput screening using a paper-based colorimetric iodide sensor (PBCIS) showed that Pd(OAc)2 and Cs2CO3 were the best catalyst and base, respectively. Aryl iodides and bromides were hydrodehalogenated to produce the reduced arenes using Pd(OAc)2 and Pd(PPh3)4 catalyst. This catalytic system showed good functional group tolerance. In addition, it was found that paraformaldehyde is the hydride source and the reducing agent for the formation of palladium nanoparticles.

A New Approach for Oxygenation Using Nitric Oxide under the Influence of N-Hydroxyphthalimide

Eikawa, Masahiro,Sakaguchi, Satoshi,Ishii, Yasutaka

, p. 4676 - 4679 (1999)

An approach for partial oxygenation through a carbocation as an intermediate was successfully developed by using nitric oxide under the influence of N-hydroxyphthalimide. Thus, a variety of benzylic ethers were converted into the corresponding partially oxidized compounds, which are difficult to prepare by conventional methods, in high yields. For example, the reaction of phthalane with NO in the presence of a catalytic amount of NHPI at 60°C gave phthalaldehyde in 80% yield. The reaction was found to proceed through the formation of a hemiacetal, such as 1-hydroxyphthalane. In addition, 1,3-di-tert-butoxymethyl benzene afforded 1,3-benzenedicarbaldehyde in good yield. On the other hand, isochroman was converted into 1,1′-oxodiisochromane under these reaction conditions. The reaction of ethers with NO in the presence of a NHPI catalyst is thought to proceed via the formation of a carbocation as an intermediate. A possible reaction path was suggested.

One-pot double benzylation of 2-substituted pyridines using palladium-catalyzed decarboxylative coupling of sp2 and sp3 carbons

Wang, Yaping,Li, Xinjian,Leng, Faqiang,Zhu, Helong,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng

, p. 3307 - 3313 (2014)

An efficient and practical decarboxylative double benzylation method for various 2-picolinic acids has been established by using a bimetallic catalytic system of palladium(II) chloride (PdCl2) and silver(I) oxide (Ag2O), which offered a variety of diarylmethane derivatives with moderate to good yields.

Nitration of alkanes with nitric acid by vanadium-substituted polyoxometalates

Shinachi, Satoshi,Yahiro, Hidenori,Yamaguchi, Kazuya,Mizuno, Noritaka

, p. 6489 - 6496 (2004)

The nitration of alkanes by using nitric acid as a nitrating agent in acetic acid was efficiently promoted by vanadium-substituted Keggin-type phosphomolybdates such as [H4PVMo11O40], [H5PV2Mo10O40], and [H 6PV3Mo9O40] as catalyst precursors. A variety of alkanes including alkylbenzenes were nitrated to the corresponding nitroalkanes as major products in moderate yields with formation of oxygenated products under mild reaction conditions. The carbon-carbon bond cleavage reactions hardly proceeded. ESR, NMR, and IR spectroscopic data show that the vanadium-substituted polyoxometalate, for example, [H4PVMo 11O40], decomposes to form free vanadium species and [PMo12O40]3- Keggin anion. The reaction mechanism involving a radical-chain path is proposed. The polyoxometalates initially abstract the hydrogen of the alkane to form the alkyl radical and the reduced polyoxometalates. The reduced polyoxometalates subsequently react with nitric acid to produce the oxidized form and nitrogen dioxide. This step would be promoted mainly by the phosphomolybdates, [PMo12O 40]n-, and the vanadium cations efficiently enhance the activity. The nitrogen dioxide promotes the further formation of nitrogen dioxide and an alkyl radical. The alkyl radical is trapped by nitrogen dioxide to form the corresponding nitroalkane.

Effects of the carbon support nature and ruthenium content on the performances of Ru/C catalysts in the liquid-phase hydrogenation of benzaldehyde to benzyl alcohol

Mironenko, Roman M.,Belskaya, Olga B.,Zaikovskii, Vladimir I.,Likholobov, Vladimir A.

, p. 923 - 930 (2015)

Abstract The hydrogenation of benzaldehyde in ethanol medium in the presence of Ru/C catalysts was shown to proceed with the preferential formation of benzyl alcohol without subsequent hydrodeoxygenation into toluene. An increase in ruthenium content of t

New CNN-type ruthenium pincer NHC complexes. Mild, efficient catalytic hydrogenation of esters

Fogler, Eran,Balaraman, Ekambaram,Ben-David, Yehoshua,Leitus, Gregory,Shimon, Linda J.W.,Milstein, David

, p. 3826 - 3833 (2011)

Figure Presented: New pincer ruthenium complexes (2-6) based on the new bipyridine-NHC ligand 1 were prepared and studied, resulting in an efficient catalytic hydrogenation of esters to the corresponding alcohols under mild conditions. Reaction of the ligand 1 with RuH(Cl)CO(PPh3) 3, followed by reaction with one equivalent of the base KHMDS, gave the mixed phosphine-NHC complex 2, incorporating a C-H-activated bipyridine ligand. Complex 2 has an octahedral structure containing two phosphorus atoms trans to each other, a hydride trans to the NHC ligand, and CO trans to the C-H-activated carbon of the bipyridine ligand. Using the precursor complex Ru(p-cymene)Cl2(CO), reaction with 1 followed by treatment of the intermediate product with one equivalent of KHMDS resulted in formation of the dichloride pincer complexes 3a and 3b, which are in equilibrium, as indicated by variable-temperature 1H NMR. Complex 3a is an octahedral, neutral, and symmetric complex with the CO ligand positioned trans to the central pyridine group of the pincer ligand and the two chlorides trans to each other, as indicated by single-crystal X-ray diffraction. Complex 3b is cationic, with an outer-sphere chloride. Reaction of the NHC ligand 1 with LiHMDS at low temperature followed by addition of RuH(Cl)CO(PPh3)3 resulted in the mixed phosphine-NHC complex 4, which has an octahedral structure containing phosphorus trans to the hydride, a CO trans to the NHC ligand, and an outer-sphere chloride. Chloride substitution by BArF- gave the X-ray-characterized complex 5. Deprotonation of complex 4 with KHMDS resulted in formation of the dearomatized complex 6. The in situ prepared 6 (from complex 4 and an equivalent of base) is among the best catalysts known for the hydrogenation of nonactivated esters to the corresponding alcohols under mild conditions.

n-Butyllithium (1 mol %)-catalyzed Hydroboration of Aldehydes and Ketones with Pinacolborane

Yang, Su Jin,Jaladi, Ashok Kumar,Kim, Jea Ho,Gundeti, Shankaraiah,An, Duk Keun

, p. 34 - 38 (2019)

A practical and efficient protocol for the hydroboration of aldehydes and ketones using a pinacolborane and alkyl lithium system is demonstrated. A systematic evaluation showed that 1 mol % n-butyllithium afforded catalyzed hydroboration of aldehydes and ketones in a short reaction time under ambient conditions. Excellent yield, functional group tolerance, short reaction time, low catalyst loading, and gram-scale synthesis are the salient features of the proposed protocol.

Design of mesoporous aluminosilicates supported (1R,2S)-(-)-ephedrine: Evidence for the main factors influencing catalytic activity in the enantioselective alkylation of benzaldehyde with diethylzinc

Abramson,Lasperas,Brunel

, p. 357 - 367 (2002)

(-)-Ephedrine, used as a model β-amino alcohol, was covalently anchored on mesoporous micelle templated aluminosilicates (Al-MTS) through nucleophilic substitution of halogenoalkyl(aryl)silane chains previously grafted on the surface. The covalent graftin

Deamination of N,O-Dialkylhydroxylamines via N-Nitroso-N,O-dialkylhydroxylamines: a New Reaction

Maskill, H.,Menneer, Iain D.,Smith, David I.

, p. 1855 - 1856 (1995)

N-Nitroso-N,O-dialkylhydroxylamines undergo acid catalysed deaminative solvolysis in aqueous solution.

Why does alkylation of the N-H functionality within M/NH bifunctional Noyori-type catalysts lead to turnover?

Dub, Pavel A.,Scott, Brian L.,Gordon, John C.

, p. 1245 - 1260 (2017)

Molecular metal/NH bifunctional Noyori-type catalysts are remarkable in that they are among the most efficient artificial catalysts developed to date for the hydrogenation of carbonyl functionalities (loadings up to ~10-5 mol %). In addition, these catalysts typically exhibit high C=0/C=C chemo- and enantioselectivities. This unique set of properties is traditionally associated with the operation of an unconventional mechanism for homogeneous catalysts in which the chelating ligand plays a key role in facilitating the catalytic reaction and enabling the aforementioned selectivities by delivering/accepting a proton (H+) via its N-H bond cleavage/formation. A recently revised mechanism of the Noyori hydrogenation reaction (Dub, P. A et al. J. Am. Chem. Soc. 2014,136,3505) suggests that the N-H bond is not cleaved but serves to stabilize the turnover-determining transition states (TDTSs) via strong N-H···O hydrogen-bonding interactions (HBIs). The present paper shows that this is consistent with the largely ignored experimental fact that alkylation of the N-H functionality within M/NH bifunctional Noyori-type catalysts leads to detrimental catalytic activity. The purpose of this work is to demonstrate that decreasing the strength of this HBI, ultimately to the limit of its complete absence, are conditions under which the same alkylation may lead to beneficial catalytic activity.

Oxidation of toluene and other examples of Ci£H bond activation by CdO2 and ZnO2 nanoparticles

Lingampalli,Gupta, Uttam,Gautam, Ujjal K.,Rao

, p. 837 - 842 (2013)

Nanoparticles of CdO2 and ZnO2 are shown to oxidize toluene primarily to benzaldehyde in the 160-180 °C range, around which temperature the nanoparticles decompose to give the oxides. The product selectivity and other features of the

Acetonyltriphenylphosphonium bromide and its polymer-supported analogues as catalysts in protection and deprotection of alcohols as alkyl vinyl ethers

Hon, Yung-Son,Lee, Chia-Fu,Chen, Rong-Jiunn,Szu, Ping-Hui

, p. 5991 - 6001 (2001)

Both acetonyltriphenylphosphonium bromide (ATPB, 1) and poly-p-styryldiphenylacetonylphosphonium bromide (A) were effective catalysts in the protection of alcohols as THP, THF, and EE ethers as well as the cleavage of THP, THF, and EE ethers to the corresponding alcohols. They could be applied to 1°, 2° and 3° alcohols, phenol and acid-labile alcohols. Both ATPB and catalyst A are excellent catalysts in the present study. It needed only 1×10-2-1.25×10-2 mol equiv. of the polymer-supported catalyst A in the reactions.

Highly chemoselective reduction of imines using a AuNPore/PhMe2SiH/water system and its application to reductive amination

Takale, Balaram S.,Tao, Shanmou,Yu, Xiaoqiang,Feng, Xiujuan,Jin, Tienan,Bao, Ming,Yamamoto, Yoshinori

, p. 7154 - 7158 (2015)

Abstract An unusually strong affinity of unsupported nanoporous gold (AuNPore) towards aldimines and ketimines has been demonstrated. By using PhMe2SiH and water as a hydrogen source and AuNPore as a catalyst, ketimines and aldimines can be reduced to the corresponding amines in high chemical yields under mild conditions. This system was also applied to the reductive amination of aldehydes and ketones.

Transfer Hydrogenation of Ketones and Imines with Methanol under Base-Free Conditions Catalyzed by an Anionic Metal-Ligand Bifunctional Iridium Catalyst

Han, Xingyou,Li, Feng,Liu, Peng,Wang, Rongzhou,Xu, Jing

, p. 2242 - 2249 (2020)

An anionic iridium complex [Cp*Ir(2,2′-bpyO)(OH)][Na] was found to be a general and highly efficient catalyst for transfer hydrogenation of ketones and imines with methanol under base-free conditions. Readily reducible or labile substituents, such as nitro, cyano, and ester groups, were tolerated under present reaction conditions. Notably, this study exhibits the unique potential of anionic metal-ligand bifunctional iridium catalysts for transfer hydrogenation with methanol as a hydrogen source.

Hydrogenation of Esters by Manganese Catalysts

Li, Fu,Li, Xiao-Gen,Xiao, Li-Jun,Xie, Jian-Hua,Xu, Yue,Zhou, Qi-Lin

, (2022/01/13)

The hydrogenation of esters catalyzed by a manganese complex of phosphine-aminopyridine ligand was developed. Using this protocol, a variety of (hetero)aromatic and aliphatic carboxylates including biomass-derived esters and lactones were hydrogenated to primary alcohols with 63–98% yields. The manganese catalyst was found to be active for the hydrogenation of methyl benzoate, providing benzyl alcohol with turnover numbers (TON) as high as 45,000. Investigation of catalyst intermediates indicated that the amido manganese complex was the active catalyst species for the reaction. (Figure presented.).

Chemoselective (Hetero)Arene Electroreduction Enabled by Rapid Alternating Polarity

Hayashi, Kyohei,Griffin, Jeremy,Harper, Kaid C.,Kawamata, Yu,Baran, Phil S.

, p. 5762 - 5768 (2022/04/15)

Conventional chemical and even electrochemical Birch-type reductions suffer from a lack of chemoselectivity due to a reliance on alkali metals or harshly reducing conditions. This study reveals that a simpler avenue is available for such reductions by simply altering the waveform of current delivery, namely rapid alternating polarity (rAP). The developed method solves these issues, proceeding in a protic solvent, and can be easily scaled up without any metal additives or stringently anhydrous conditions.

Photophysics of Perylene Diimide Dianions and Their Application in Photoredox Catalysis

Li, Han,Wenger, Oliver S.

supporting information, (2021/12/23)

The two-electron reduced forms of perylene diimides (PDIs) are luminescent closed-shell species whose photochemical properties seem underexplored. Our proof-of-concept study demonstrates that straightforward (single) excitation of PDI dianions with green

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