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108-46-3

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108-46-3 Usage

Uses

Different sources of media describe the Uses of 108-46-3 differently. You can refer to the following data:
1. Manufacture of rubber products, wood adhesives, dyes, explosives, and cosmetics; in photography.
2. 1. It can be used as the raw materials for the production of synthetic resins, adhesives, dyes and ultraviolet absorbing agent. It can also be used as the dipped cord of tire. Medically it can be used as the disinfection antiseptic agent. 2. Resorcinol is also known as 1, 3-hydroquinone. In the field of pesticides, it can be used as the intermediate 3-chloro-4-methyl coumarin and herbicide oxyfluorfen in the synthesis of pesticides coumaphos. It can also be used for the production of dyes, specialty coatings, pharmaceuticals, photographic material, synthetic resins, adhesives, and cosmetics. 3. Resorcinol is mainly used for the field of rubber adhesives, synthetic resins, dyes, preservative, pharmaceutical and analytical reagents. Resorcinol is similar with phenol and cresol. It can generate condensation polymer through the reaction with formaldehyde. It can be used for making glue silk and the adhesive agent of tire cord for nylon-purpose, making wood glue, and being as the adhesive for vinyl material and metal. Resorcinol is the intermediate of many kinds of azo dyes and fur dyes as well as the raw material of pharmaceutical intermediates, p-nitrogen salicylic acid. Resorcinol has bactericidal effects and can be used as preservatives for being supplied to cosmetics and dermatological drugs pastes and ointments. The resorcinol derivatives, β-methylumbelliferone can be used as the intermediate for optical bleach; tri-nitro resorcinol is detonator. There is also a considerable amount of resorcinol being used in the production of benzophenone-class ultraviolet absorbers. This product can irritate the skin and mucous membranes, can cause poisoning disease through the rapid absorption by the skin. Minimum lethal dose of rat being subject to subcutaneous injection is 450mg/kg. 4. It can be applied to the fields of photographic film, medicines, dyes and chemical fiber industry. 5. It can also be used as reagents for analysis. 6. It can be used for characterization and determination of zinc, lead, tartaric acid, nitrate and nitrite through colorimetric method; it can also applied to the colorimetric reaction for measuring sugar and Furfuryl alcohol; as the reagent for detecting ketone sugars and lignin; it can also applied to the salt reagent of diazonium compound as well as to organic synthesis.
3. Resorcinol is used in the manufacture of resorcinol–formaldehyde resins, resin adhesives, dyes, drugs, andexplosives; in tanning; in cosmetics; and in dyeing and printing textiles.
4. In very mild solutions, resorcinol is used as an anti-septic and soothing preparation for itchy skin. In slightly higher concentrations, resorcinol removes the top layer of the stratum corneum and is used particularly in cases of acne. In still higher concentrations, it can act as an aggressive surface skin exfoliant. Resorcinol can also be used as a preservative. While it is a beneficial skin care ingredient when used in low concentrations, it causes irritation in higher concentrations with a strong burning sensation and a reddening of the skin. used in high concentrations as a peel, resorcinol may cause a variety of problems, including swelling. It is is obtained from various resins.
5. A benzene derivative used as keratolytic and antiseborrheic. Also used in veterinary medicine as a topical antipruritic and antiseptic (has been used as intestinal antiseptic).
6. anthelmintic
7. An aromatic alcohol used as a chemical intermediate

description

Resorcinol has bactericidal, fungicidal and anti-itching effect with the bactericidal effect being 1/3 of the phenol and also a low irritating and corrosive property. At low concentration, it can play the role promoting the regeneration of horny while having keratin exfoliation effect at high concentration. It is mainly used for rubber adhesives, plastics, synthetic resins, synthetic fibers, dyes, preservatives, anti-itch, anti-fungal agent, analytical reagent and can also be used to treat ringworm, eczema, seborrheic dermatitis, acne and psoriasis. Figure 1 3D structure of resorcinol. The above information is edited by the lookchem of Dai Xiongfeng.

Chemical Properties

Different sources of media describe the Chemical Properties of 108-46-3 differently. You can refer to the following data:
1. It is white needle-like crystal. It will become pink upon exposure to light and air or contact with iron. It has a sweet taste. It is soluble in water, ethanol, amyl alcohol, easily soluble in ether, glycerol, slightly soluble in chloroform, carbon disulfide as well as in benzene.
2. Resorcinol is odorless.
3. crystals or powder
4. Resorcinol is a white crystalline solid with a characteristic odor and a sweetish taste. Turns pink on expo- sure to air or light, or contact with iron.

reaction

The chemical property of resorcinol is active and it can participate in the following four kinds of reaction. (1) It can have reaction with sodium amalgam, water for production of dihydro-resorcinol (1, 3-cyclohexanedione). (2) It can generate ester with reaction with acid anhydride. (3) It can react with hydroxylamine in a diketone type to generate oxime. (4) In the action of concentrated sulfuric acid or zinc chloride, it can react with phthalic anhydride to generate fluorescent dye-fluorescent yellow.

Indications

Different sources of media describe the Indications of 108-46-3 differently. You can refer to the following data:
1. It can be used for the treatment of seborrheic dermatitis, acne, superficial skin fungal infections, tinea versicolor, calluses, corns, and common warts.
2. Resorcinol (resorcin), a phenol derivative, is less keratolytic than salicylic acid. This drug is an irritant and sensitizer and reported to be both bactericidal and fungicidal. Solutions containing 1% to 2% have been used in preparations for seborrhea, acne, and psoriasis.

Side effects

1, it can cause contact dermatitis and has weak irritation effect on skin and mucous membrane. This product, when being absorbed through broken skin and wound surface in the large amount, can lead to myxedema. 2, because this product can be absorbed through the skin or ulcers, and thus is not suitable or being applied to infants and young children in high concentration and large-scale. 3, poisoning symptoms include diarrhea, nausea, vomiting, stomach pain, dizziness, severe or persistent headache, fatigue or weakness, being prone to excitement or irritability, sleepiness, sweating, bradycardia, and shortness of breath. 4, applying this product to the wound of children can lead to methaemoglobinaemia. 5, since this product has anti-thyroid effects, systemic effects is similar as phenol poisoning, but often accompanied with convulsions.

Precautions

1, it can turn pale hair to black color; it can cause skin redness and scaling at a few days after treatment; take this drug with caution. 2, dark-skinned patients may be caused by its stimulation of pigment generation. 3, when being used in combination with soaps, cleansers, acne preparations, preparations containing alcohol or acid-dimensional A, it can cause skin irritation or excessive drying effect. 4, it has anti-thyroid effects; it can lead to myxedema upon long term use (especially used in ulcer surface). 5. This product is toxic and thus this product can’t subject to systemic or long-term use; avoid applying it to the broken skin wound in order to preventing poisoning.

Applications

Resorcinol is an important raw material for organic synthesis. It is mainly used as the raw material of rubber adhesives, raw analysis reagents, drugs and preservatives, dyes, synthetic resin. For example, eosin is an important triphenylmethane dye with red dying which is mainly used for yarn dyeing. It is made from the following process: first generate its intermediate fluorescent yellow thorough the co-heating between resorcinol and phthalic anhydride in the presence of zinc chloride or concentrated sulfuric acid, then apply tetra-bromination to generate it. Eosin is commonly used to produce red ink, also be used as biological material such as the staining agent for microscopic examination. If the intermediate fluorescent yellow is subject to bromination in acetic acid solution, only di-bromination can occur; further co-heating with mercuric acetate can obtain mercurochrome (also known as red mercury bromine) which is an important antiseptic disinfectant. It is easily soluble in water with its 2% aqueous solution being the daily-used “red syrup” for disinfection. The alcohol and acetone solution of mercurochrome may also be used for skin disinfection. Put resorcinol and hexanoic acid for acylation reaction and further reduction can generate 4-n-hexyl hydroquinone which is also a kind of disinfectant. In medicine, it is also used as a topical anti-itch agent and a digestive agent of the intestinal tract.

Toxicity

GRAS (FEMA).

Production

1. Benzene sulfonic acid is sulfonated with oleum; further go through neutralization, alkaline melting, acidification, n-butanol extraction, evaporation of the solvent, and distillation to obtain the finished products. 2. It can be produced through the hydrogenation of m-dinitrobenzene into m-phenylenediamine which is further subject to hydrolysis to get the finished product. 3. It can be produced from the hydrolysis of m-aminophenol. Resorcinol can also derived from benzene and propylene using peroxide di-isopropylbenzene method with the process being similar as isopropylbenzene production. Put benzene, 65% fuming sulfuric acid and sodium sulfate separately into the reactor; control the reaction temperature at 75 ℃ to obtain the sulphonate. Then add anhydrous sodium sulfate to this sulphonate, stir and heat to 175 ℃ for dissolving it; Add sulfur trioxide at this temperature and continue the reaction for an additional 1.5h to generate di-sulphonate (with the content of benzene disulfonic acid being 75%). Use dilute alkali to neutralize the di-sulphonate and remove the excess amount of sulfate salt; the resulting sodium benzene di-sulfonate is gradually added into the molten sodium hydroxide 290 °C; raise the temperature to 325 °C within 15min and further dissolve the alkali melting substance in water; acidify it with sulfuric acid and extract with ether; evaporate the solvent to obtain the finished resorcinol products.

Occurrence

Reported found in roasted barley, cane molasses, beer, red wine, white wine, special wine and coffee.

Definition

ChEBI: A benzenediol that is benzene dihydroxylated at positions 1 and 3.

Aroma threshold values

Detection: 6 to 40 ppm

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 8727, 1994 DOI: 10.1016/S0040-4039(00)78482-6

General Description

Very white crystalline solid that becomes pink on exposure to light if not completely pure. Burns although ignition is difficult. Density approximately 1.28 g / cm3. Irritating to skin and eyes. Toxic by skin absorption. Used to make plastics and pharmaceuticals.

Air & Water Reactions

Hygroscopic. Soluble in water.

Reactivity Profile

Resorcine is a weak organic acid. Incompatible with acetanilide, albumin, alkalis, antipyrine, camphor, iron salts, menthol, spirit nitrous ether, and urethane. Can react with oxidizing materials . Has a potentially explosive reaction with concentrated nitric acid [Lewis]. Turns pink on contact with iron.

Hazard

Irritant to skin and eyes. Questionable car- cinogen.

Health Hazard

Different sources of media describe the Health Hazard of 108-46-3 differently. You can refer to the following data:
1. Inhalation of vapors or dust causes irritation of respiratory tract. Ingestion causes burns of mucous membranes, severe diarrhea, pallor, sweating, weakness, headache, dizziness, tinnitus, shock, and severe convulsions; may also cause siderosis of the spleen and tubular injury to the kidney. Contact with eyes causes irritation. Can be absorbed from wounds or through unbroken skin, producing severe dermatitis, methemoglobinemia, cyanosis, convulsions, tachycardia, dyspnea, and death.
2. The acute oral toxicity of resorcinol is moderate in most test animals. It is less toxic than phenol or catechol. Ingestion or skin absorption can cause methemoglobinemia, cyanosis, and convulsions. Vapors or dusts are irritant to mucous membranes. Contact with the skin or eyes can cause strong irritation. An amount of 100 mg caused severe irritation in rabbit eyes.LD50 value, oral (rats): 301 mg/kg (NIOSH 1986).

Fire Hazard

Behavior in Fire: Containers may explode.

Flammability and Explosibility

Nonflammable

Contact allergens

Resorcinol is used in hairdressing as a modifier (or a coupler) of the PPD group of dyes. It is the least frequent sensitizer in hairdressers. It is also used in resins, in skin treatment mixtures, and for tanning. Severe cases of dermatitis due to resorcinol contained in wart preparations have been reported.

Biochem/physiol Actions

Resorcinol is an aromatic alcohol serves as an antiseptic. It reduces pain from painful nodules in patients suffering from Hidradenitis suppurativa (HS).

Safety Profile

Human poison by ingestion. Experimental poison by ingestion, intraperitoneal, parenteral, and subcutaneous routes. Moderately toxic experimentally by skin contact and intravenous routes. Questionable carcinogen with experimental tumorigenic data. Human mutation data reported. A skin and severe eye irritant. It can cause systemic poisoning by acting as both a blood and nerve poison. In a suitable solvent, this material can readily be absorbed through human skin and can cause local hyperemia, itching, dermatitis, edema, and corrosion associated with enlargement of regonal lymph glands as well as serious systemic disorders such as restlessness, methemoglobinemia, cyanosis, convulsions, tachycardia, dyspnea, and death. These same symptoms can be induced by ingestion of the material. For poisoning, treat symptomatically. Get medical advice. Used as a topical antiseptic and keratolytic agent. Combustible when exposed to heat or flame; can react with oxidming materials. To fight fEe, use water, CO2, dry chemical. Potentially explosive reaction with concentrated nitric acid. Incompatible with acetadde, alkalies, ferric salts, spirit nitrous ether, urethan. When heated to decomposition it emits acrid smoke and irritating fumes

Potential Exposure

Resorcinol is weakly antiseptic; resorcinol compounds are used in the production of resorcinol-formaldehyde adhesives; or as an intermediate; in pharmaceuticals and hair dyes for human use. Major industrial uses are as adhesives in rubber products and tires, wood adhesive resins, and as ultraviolet absorbers in polyolefin plastics. Resorcinol is also a by-product of coal conversion and is a component of cigarette smoke. Thus, substantial opportunity exists for human exposure.

Carcinogenicity

Acute Toxicity. The primary signs of intoxication resemble those induced by phenol, and include initial stimulation of the CNS, followed by depression, renal glomerular and tubular degeneration, central hepatic necrosis, myocardial depression, pruritus, and reddening of the skin. Resorcinol has been reported to be less toxic than phenol or pyrocatechol by oral and dermal routes. Resorcinol is a simple aromatic chemical (1,3-benzenediol) that has found widespread use, particularly as a coupler in hair dyes. Clinical experience clearly shows that resorcinol is a skin sensitizer, although several predictive tests have been negative. In a local lymph node assay performed in accordance with OECD Guideline 429, resorcinol was identified as a skin sensitizer. Few reports of the toxicity of resorcinol have been published. Oral ingestion in humans may cause methemoglobinemia, cyanosis, and convulsions, whereas dermal exposure has been reported to cause dermatitis, hyperemia, and pruritus. Industrial inhalation exposures are rather rare, but could occur in any industry if the compound is heated beyond 300°F. Pathology reported for humans includes anemia, marked siderosis of the spleen and marked tubular injury in the kidney, fatty changes of the liver, degenerative changes in the kidney, fatty changes of the heart muscle, moderate enlargement and pigmentation of the spleen, and edema and emphysema of the lungs.

Shipping

UN2876 Resorcinol, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Crystallise resorcinol from *benzene, toluene or *benzene/diethyl ether. The benzoate has m 117o. [Beilstein 6 IV 2069.]

Incompatibilities

Reacts with oxidizers, nitric acid; oil, ferric salts; methanol, acetanilide, albumin, antipyrene, alkalies, urethane, ammonia, amino compounds. Hygroscopic; absorbs moisture from the air.

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations govern- ing storage, transportation, treatment, and waste disposal. Dissolve in a combustible solvent and incinerate.

Check Digit Verification of cas no

The CAS Registry Mumber 108-46-3 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 8 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 108-46:
(5*1)+(4*0)+(3*8)+(2*4)+(1*6)=43
43 % 10 = 3
So 108-46-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H

108-46-3 Well-known Company Product Price

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

  • (A13080)  Resorcinol, 99%   

  • 108-46-3

  • 50g

  • 148.0CNY

  • Detail
  • Alfa Aesar

  • (A13080)  Resorcinol, 99%   

  • 108-46-3

  • 250g

  • 370.0CNY

  • Detail
  • Alfa Aesar

  • (A13080)  Resorcinol, 99%   

  • 108-46-3

  • 1000g

  • 1336.0CNY

  • Detail
  • Alfa Aesar

  • (A13080)  Resorcinol, 99%   

  • 108-46-3

  • 5000g

  • 5729.0CNY

  • Detail
  • Alfa Aesar

  • (36248)  Resorcinol, ACS, 99.0-100.5%   

  • 108-46-3

  • 25g

  • 257.0CNY

  • Detail
  • Alfa Aesar

  • (36248)  Resorcinol, ACS, 99.0-100.5%   

  • 108-46-3

  • 100g

  • 638.0CNY

  • Detail
  • Alfa Aesar

  • (36248)  Resorcinol, ACS, 99.0-100.5%   

  • 108-46-3

  • 500g

  • 3190.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1201)  Resorcinol  pharmaceutical secondary standard; traceable to USP, PhEur

  • 108-46-3

  • PHR1201-500MG

  • 718.73CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000012)  Hymecromone impurity A  European Pharmacopoeia (EP) Reference Standard

  • 108-46-3

  • Y0000012

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000767)  Resorcinol  European Pharmacopoeia (EP) Reference Standard

  • 108-46-3

  • Y0000767

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (53363)  Resorcinol  certified reference material, TraceCERT®

  • 108-46-3

  • 53363-100MG

  • 968.76CNY

  • Detail
  • USP

  • (1602003)  Resorcinol  United States Pharmacopeia (USP) Reference Standard

  • 108-46-3

  • 1602003-200MG

  • 4,662.45CNY

  • Detail

108-46-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name resorcinol

1.2 Other means of identification

Product number -
Other names 1,3-diethynylenebenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:108-46-3 SDS

108-46-3Synthetic route

3-allyloxyphenol
1616-51-9

3-allyloxyphenol

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol for 0.5h; Heating;98%
3-hydroxyphenylboronic acid
87199-18-6

3-hydroxyphenylboronic acid

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 48h; Green chemistry;98%
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 48h; UV-irradiation;98%
With dihydrogen peroxide In water at 20℃; for 0.5h;91%
m-phenylenediamine
108-45-2

m-phenylenediamine

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With sulfuric acid; water at 230℃; for 6h; Large scale;96.46%
Stage #1: m-phenylenediamine In water at 20℃; for 0.5h;
Stage #2: With sodium nitrite In water at 20℃; for 5h; Time;
80%
With hydrogenchloride at 180℃;
With sulfuric acid In water at 230℃; under 15001.5 Torr; for 7.5h; Reagent/catalyst; Temperature; Pressure; Autoclave;372 g
4-Bromoresorcinol
6626-15-9

4-Bromoresorcinol

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With sodium sulfite In water at 20℃; for 18h; Kinetics; Mechanism; Temperature; Green chemistry;96%
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With sodium trimethylsilanethiolate In various solvent(s) at 185℃; for 24h; Mechanism; Product distribution; other reagents, other aryl methyl ethers;95%
With hexamethyldisilathiane; sodium methylate In various solvent(s) at 185℃; for 24h;95%
With L-Selectride In tetrahydrofuran at 67℃; for 96h;93%
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 3h; Concentration; Autoclave; Inert atmosphere; Green chemistry;92%
With pyridinium p-toluenesulfonate for 0.025h; microwave irradiation;75%
O-methylresorcine
150-19-6

O-methylresorcine

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;95%
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;95%
With aluminium(III) iodide In dimethyl sulfoxide; acetonitrile at 80℃; for 48h;78%
With aluminium(III) iodide; dimethyl sulfoxide In acetonitrile at 80℃; for 18h;78%
With aluminium(III) iodide; calcium oxide In acetonitrile at 80℃; for 18h;18%
resorcin bis(tetrahydropyranyl)ether
30778-88-2

resorcin bis(tetrahydropyranyl)ether

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With montmorillonite K-10 In methanol at 40 - 50℃; for 0.6h;94%
1,3-di(2-hydroperoxy-2-propyl)benzene
721-26-6

1,3-di(2-hydroperoxy-2-propyl)benzene

A

acetone
67-64-1

acetone

B

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
sulfur trioxide In 4-methyl-2-pentanone at 70℃; for 0.166667h; Product distribution / selectivity;A n/a
B 94%
3-Iodophenol
626-02-8

3-Iodophenol

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With glycolic Acid; copper hydroxide; sodium hydroxide In water; dimethyl sulfoxide at 120℃; for 6h; Inert atmosphere; Schlenk technique;93%
With formic acid; oxygen; triethylamine; copper(ll) bromide In acetonitrile at 20℃; for 48h; Irradiation;90%
With cesium hydroxide In water; dimethyl sulfoxide at 120℃; for 24h; Sealed tube; Inert atmosphere;88%
With copper(I) oxide; 2-(N,N-dimethylamino)ethanol; water; potassium hydroxide In dimethyl sulfoxide at 100℃; for 24h; Reagent/catalyst; Temperature; Inert atmosphere;87%
Kalischmelze;
1,3-bis(allyloxy)benzene
13594-95-1

1,3-bis(allyloxy)benzene

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol for 1h; Heating;92%
m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite at 12.5 - 90℃;91.8%
With sulfuric acid; water; sodium nitrite at -5 - 40℃; for 2h; Reagent/catalyst; Temperature;74.5%
Stage #1: m-Hydroxyaniline With sulfuric acid; sodium nitrite In water at -8 - 25℃; for 0.25h;
Stage #2: With water In acetic acid butyl ester at 75 - 80℃; for 0.25h;
55%
With sulfuric acid Diazotization.Verkochen der Diazoniumsulfatloesung;
Stage #1: m-Hydroxyaniline With hydrogenchloride; sodium nitrite In water at 1℃; for 0.5h;
Stage #2: With potassium carbonate In water at 30℃; for 0.5h; Temperature;
1,3-O-bis(tert-butyldimethylsilyl)resorcinol
120951-86-2

1,3-O-bis(tert-butyldimethylsilyl)resorcinol

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With potassium fluoride; hydrogen bromide In N,N-dimethyl-formamide at 25℃; for 2h;91%
1,3-phenylenediboronic acid
4612-28-6

1,3-phenylenediboronic acid

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With Fe2O3-SiO2 nanoparticles; air In water at 50℃; for 3h; Green chemistry;89%
With [Cu6I2(μ4-I)2(μ4-5-phpymt)2]; triethylamine In water; acetonitrile for 48h; Catalytic behavior; Solvent; Time; UV-irradiation;74%
C18H30O4

C18H30O4

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With aluminum (III) chloride; sodium iodide In methanol at 60℃; for 24h; Reagent/catalyst; Solvent;89%
allyl 3-acetoxyphenyl ether
3993-32-6

allyl 3-acetoxyphenyl ether

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol for 1.5h; Heating;86%
3-Bromophenol
591-20-8

3-Bromophenol

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With copper(I) oxide; tetra(n-butyl)ammonium hydroxide; 1,10-phenanthroline-4,7-diol In water at 110℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry;86%
1,3-bis(methoxymethyl)resorcinol
57234-29-4

1,3-bis(methoxymethyl)resorcinol

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With bismuth(III) chloride In water; acetonitrile at 50℃; for 2h;85%
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

A

O-methylresorcine
150-19-6

O-methylresorcine

B

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With hydrogen iodide at 25℃; for 24h; Inert atmosphere;A 12%
B 85%
With copper(I) oxide; sodium methylate In methanol at 185℃; for 12h; Autoclave;A 50%
B 43%
1,3-bis(trimethylsiloxy)benzene
4520-29-0

1,3-bis(trimethylsiloxy)benzene

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With nano magnetic sulfated zirconia (Fe3O4 at ZrO2/SO42-) In neat (no solvent) at 20℃; for 0.5h; Green chemistry;85%
(E)-3-(2,4-dimethoxyphenyl)-2-propenoic acid
16909-09-4

(E)-3-(2,4-dimethoxyphenyl)-2-propenoic acid

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With hydrogenchloride; water at 250℃; under 37503.8 Torr; for 4.5h; Sealed tube; Inert atmosphere;84%
3-monochlorophenol
108-43-0

3-monochlorophenol

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; water at 100℃; for 17h;83%
Kalischmelze;
bei der Kalischmelze;
In water Quantum yield; Ambient temperature; Irradiation; presence of O2 investigated;
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
Stage #1: 3,5-dihydroxyphenol With sodium hydroxide; hydrogen; Rh/Al2O3 at 20℃; under 2585.81 Torr; for 12h;
Stage #2: With sulfuric acid for 9h; Heating; Further stages.;
82%
With sodium tetrahydroborate; water
5-methoxyresorcinol
2174-64-3

5-methoxyresorcinol

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
Stage #1: 5-methoxyresorcinol With sodium hydroxide; hydrogen; Rh/Al2O3 In water under 2585.81 Torr; for 12h;
Stage #2: With sulfuric acid for 9h; Heating; Further stages.;
80%
1,3-Diiodobenzene
626-00-6

1,3-Diiodobenzene

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With β-D-glucose; copper(II) acetate monohydrate; potassium hydroxide In water; dimethyl sulfoxide at 20 - 120℃; for 24h;80%
Resorcinol monoacetate
102-29-4

Resorcinol monoacetate

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With copper dichloride In methanol; water for 3h; Heating;75%
2,6-Dihydroxybenzoic acid
303-07-1

2,6-Dihydroxybenzoic acid

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With silver carbonate In dimethyl sulfoxide at 120℃; for 16h;71%
Destillation;
With hydrogenchloride at 120℃; pH=1.40; Activation energy; Kinetics; Further Variations:; Temperatures; pH-values;
3-Benzyloxyphenyl acetate
81499-29-8

3-Benzyloxyphenyl acetate

A

Resorcinol monoacetate
102-29-4

Resorcinol monoacetate

B

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With pentamethylbenzene,; boron trichloride In dichloromethane at -78℃; for 0.333333h;A 26%
B 71%
hydrogenchloride
7647-01-0

hydrogenchloride

7,7,7,15,15,15-hexamethyl-6,8,14,16-tetraoxa-7,15-distibatricyclo[11.3.1.1.(9,13)]octadeca-1,3,5,9,11,13-hexaene
171001-66-4

7,7,7,15,15,15-hexamethyl-6,8,14,16-tetraoxa-7,15-distibatricyclo[11.3.1.1.(9,13)]octadeca-1,3,5,9,11,13-hexaene

A

trimethylantimony dichloride
13059-67-1, 22810-79-3, 91108-42-8

trimethylantimony dichloride

B

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
In ethanol excess soln. of acid addn. to Sb-compd., heating (3 h, reflux, water bath), soln. pouring to petri dish; sepn. by different solubility in benzene;A 70%
B 69%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

recorcinol
108-46-3

recorcinol

7-hydroxy-4-methyl-chromen-2-one
90-33-5, 79566-13-5

7-hydroxy-4-methyl-chromen-2-one

Conditions
ConditionsYield
With trifluoroacetic acid at 100℃; for 0.5h; Pechmann condensation; Microwave irradiation; regioselective reaction;100%
With silica-supported methanesulfonic acid catalyst In octadecane at 160℃; for 2h; Pechmann reaction;99%
With iron(III) chloride In neat (no solvent) at 70℃; for 12h; Pechmann Condensation; Green chemistry;99%
4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

recorcinol
108-46-3

recorcinol

3-(4-nitrobenzoyloxy)phenyl 4-nitrobenzoate
187264-29-5

3-(4-nitrobenzoyloxy)phenyl 4-nitrobenzoate

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 20℃; for 24h;100%
With tetralin at 160℃;
With pyridine at 100℃;
With pyridine In toluene Heating;
isobutyryl chloride
79-30-1

isobutyryl chloride

recorcinol
108-46-3

recorcinol

1-(2,4-dihydroxyphenyl)-2-methyl-1-propanone
29048-54-2

1-(2,4-dihydroxyphenyl)-2-methyl-1-propanone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at 20℃;100%
at 90℃;
With aluminium trichloride; nitrobenzene at 40 - 50℃;
ethyl 2-oxocyclohexane carboxylate
1655-07-8

ethyl 2-oxocyclohexane carboxylate

recorcinol
108-46-3

recorcinol

3-hydroxy-7,8,9,10-tetrahydrobenzo[c]chromen-6-one
3722-44-9

3-hydroxy-7,8,9,10-tetrahydrobenzo[c]chromen-6-one

Conditions
ConditionsYield
With sulfuric acid at 0 - 20℃; for 1h; Pechmann condensation;100%
With sulfuric acid at 20℃; for 24h;98%
With aluminum oxide; methanesulfonic acid at 20℃; for 0.166667h; Pechmann reaction;96%
isobutyric Acid
79-31-2

isobutyric Acid

recorcinol
108-46-3

recorcinol

1-(2,4-dihydroxyphenyl)-2-methyl-1-propanone
29048-54-2

1-(2,4-dihydroxyphenyl)-2-methyl-1-propanone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at 90℃; for 1.5h; Inert atmosphere;100%
With zinc(II) chloride at 125 - 140℃;
With boron trifluoride
ethyl 2-chloro-3-oxo-butyrate
609-15-4

ethyl 2-chloro-3-oxo-butyrate

recorcinol
108-46-3

recorcinol

3-chloro-4-methylumbelliferone
6174-86-3

3-chloro-4-methylumbelliferone

Conditions
ConditionsYield
With trifluoroacetic acid at 100℃; for 0.5h; Pechmann condensation; Microwave irradiation; regioselective reaction;100%
With zirconium(IV) oxychloride In ethanol at 60 - 65℃; for 24h; Pechmann reaction;98%
With aluminum potassium sulfate dodecahydrate at 65℃; for 2h; Pechmann condensation; Neat (no solvent);93%
recorcinol
108-46-3

recorcinol

4-Bromoresorcinol
6626-15-9

4-Bromoresorcinol

Conditions
ConditionsYield
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 2h; Heating;100%
With dihydrogen peroxide; potassium bromide In water; acetonitrile96%
With DMd; sulfuric acid; sodium bromide In acetone at 20℃; for 0.0166667h;95%
chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

recorcinol
108-46-3

recorcinol

1,3-bis(methoxymethyl)resorcinol
57234-29-4

1,3-bis(methoxymethyl)resorcinol

Conditions
ConditionsYield
Stage #1: recorcinol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Inert atmosphere;
Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; mineral oil at 20℃; for 27h; Inert atmosphere;
100%
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;99%
Stage #1: recorcinol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Inert atmosphere;
Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 5h;
95%
(4-chlorophenyl)(2-hydroxy-3,3-dimethyl-2,3-dihydroindol-1-yl)methanone
51459-50-8

(4-chlorophenyl)(2-hydroxy-3,3-dimethyl-2,3-dihydroindol-1-yl)methanone

recorcinol
108-46-3

recorcinol

(4-Chloro-phenyl)-[2-(2,4-dihydroxy-phenyl)-3,3-dimethyl-2,3-dihydro-indol-1-yl]-methanone
91751-58-5

(4-Chloro-phenyl)-[2-(2,4-dihydroxy-phenyl)-3,3-dimethyl-2,3-dihydro-indol-1-yl]-methanone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In 1,4-dioxane at 40℃; for 10h;100%
With boron trifluoride diethyl etherate In 1,4-dioxane at 40℃; for 10h;100%
Dodecanal
112-54-9

Dodecanal

recorcinol
108-46-3

recorcinol

C-undecylcalix[4]resorcinarene
847018-76-2

C-undecylcalix[4]resorcinarene

Conditions
ConditionsYield
ytterbium (III) tris-[tris-(nonafluorobutanesulfonyl)methide] In ethanol for 48h; Heating / reflux;100%
With hydrogenchloride In ethanol; water at -10 - 90℃; for 20.1667h;82%
With hydrogenchloride In ethanol at 20 - 90℃; for 17h;76%
3-hydroxyphenylacetic acid
621-37-4

3-hydroxyphenylacetic acid

recorcinol
108-46-3

recorcinol

1-(2,4-dihydroxyphenyl)-2-(3-hydroxyphenyl)ethanone
89019-84-1

1-(2,4-dihydroxyphenyl)-2-(3-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate for 1.5h; Reflux;100%
With boron trifluoride diethyl etherate at 60 - 70℃; for 1h;93%
With boron trifluoride diethyl etherate In toluene at 90℃; for 2h;57%
With boron trifluoride diethyl etherate at 110℃; for 2h; Inert atmosphere;
With boron trifluoride diethyl etherate In N,N-dimethyl-formamide at 90℃; for 2h;
m-methoxyphenylacetic acid
1798-09-0

m-methoxyphenylacetic acid

recorcinol
108-46-3

recorcinol

1-(2,4-dihydroxyphenyl)-2-(3-methoxyphenyl)ethanone
89019-83-0

1-(2,4-dihydroxyphenyl)-2-(3-methoxyphenyl)ethanone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at 85℃; for 3h;100%
With boron trifluoride diethyl etherate at 60 - 70℃; for 1h;96%
With boron trifluoride diethyl etherate at 80 - 90℃; Inert atmosphere;74%
methylphosphonous acid diphenyl ester
38316-42-6

methylphosphonous acid diphenyl ester

recorcinol
108-46-3

recorcinol

oligomeric resorcinol methylphosphonate

oligomeric resorcinol methylphosphonate

Conditions
ConditionsYield
at 60 - 241℃; under 0.750075 - 15.201 Torr; for 11h;100%
recorcinol
108-46-3

recorcinol

C88H68Br4O8

C88H68Br4O8

C100H76O12

C100H76O12

Conditions
ConditionsYield
With potassium carbonate; copper(II) oxide In pyridine for 168h; Heating;100%
cyclohexylacetic acid chloride
23860-35-7

cyclohexylacetic acid chloride

recorcinol
108-46-3

recorcinol

2-cyclohexyl-1-(2,4-dihydroxyphenyl)ethanone
470485-27-9

2-cyclohexyl-1-(2,4-dihydroxyphenyl)ethanone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at 20℃; Inert atmosphere;100%
With aluminium trichloride In dichloromethane at 20 - 70℃; for 4h;40%
Conditions
ConditionsYield
With hydrogenchloride In ethanol at 80℃; for 18h;100%
benzyl bromide
100-39-0

benzyl bromide

2-bromo-5-methoxy-benzoic acid
22921-68-2

2-bromo-5-methoxy-benzoic acid

recorcinol
108-46-3

recorcinol

3-(Benzyloxy)-8-methoxy-6H-benzo[c]chromen-6-one
845438-83-7

3-(Benzyloxy)-8-methoxy-6H-benzo[c]chromen-6-one

Conditions
ConditionsYield
Stage #1: 2-bromo-5-methoxy-benzoic acid; recorcinol With sodium hydroxide; copper(II) sulfate
Stage #2: benzyl bromide With caesium carbonate
100%
recorcinol
108-46-3

recorcinol

5,6-dichlorofluorescein
86166-34-9

5,6-dichlorofluorescein

Conditions
ConditionsYield
Stage #1: 4,5-dichlorophthalic acid With methanesulfonic acid at 90℃; for 1h;
Stage #2: recorcinol at 80 - 105℃; for 1h;
100%
2-(1-benzyl-pyrrol-2-yl)-4,6-dichloro-[1,3,5]triazine
35252-49-4

2-(1-benzyl-pyrrol-2-yl)-4,6-dichloro-[1,3,5]triazine

recorcinol
108-46-3

recorcinol

2-(1-benzyl-1H-pyrrole-2-yl)-4,6-bis(2,4-dihydroxyphenyl)-1,3,5-triazine

2-(1-benzyl-1H-pyrrole-2-yl)-4,6-bis(2,4-dihydroxyphenyl)-1,3,5-triazine

Conditions
ConditionsYield
Stage #1: 2-(1-benzyl-pyrrol-2-yl)-4,6-dichloro-[1,3,5]triazine; recorcinol With aluminum (III) chloride In xylene at 50 - 85℃; for 3h; Friedel Crafts Acylation;
Stage #2: With hydrogenchloride In water
100%
1,1'-bis(ethenyl-4-pyridyl)ferrocene
222165-10-8

1,1'-bis(ethenyl-4-pyridyl)ferrocene

recorcinol
108-46-3

recorcinol

1,1'-bis(ethenyl-4-pyridyl)ferrocene resorcinol

1,1'-bis(ethenyl-4-pyridyl)ferrocene resorcinol

Conditions
ConditionsYield
In ethanol at room temp. for 7 d; elem. anal.;100%
9-benzyl-6-chloro-9H-purine
1928-76-3

9-benzyl-6-chloro-9H-purine

recorcinol
108-46-3

recorcinol

4-(9-phenylmethyl-9H-purin-6-yl)-benzene-1,3-diol
1241556-45-5

4-(9-phenylmethyl-9H-purin-6-yl)-benzene-1,3-diol

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; 1,1,1,3',3',3'-hexafluoro-propanol at 60℃; for 24h;100%
With aluminum (III) chloride In 1,2-dichloro-ethane for 0.5h; Reflux;51%
recorcinol
108-46-3

recorcinol

C6H6O2*2C15H22O5

C6H6O2*2C15H22O5

Conditions
ConditionsYield
In methanol100%
1,1,3,3-tetramethyldisilazane
15933-59-2

1,1,3,3-tetramethyldisilazane

recorcinol
108-46-3

recorcinol

1,3-bis(dimethylsilyloxy)benzene
138219-50-8

1,3-bis(dimethylsilyloxy)benzene

Conditions
ConditionsYield
With dimethylmonochlorosilane In tetrahydrofuran Reflux;100%
oxirane
75-21-8

oxirane

methyloxirane
75-56-9, 16033-71-9

methyloxirane

recorcinol
108-46-3

recorcinol

C38H70O14

C38H70O14

Conditions
ConditionsYield
Stage #1: methyloxirane; recorcinol With potassium hydroxide In toluene at 48.8789℃; for 1.5h; Under N2;
Stage #2: oxirane at 48.8789℃; for 2h;
99.7%
acetyl chloride
75-36-5

acetyl chloride

recorcinol
108-46-3

recorcinol

Resorcinol diacetate
108-58-7

Resorcinol diacetate

Conditions
ConditionsYield
Stage #1: acetyl chloride; recorcinol In chloroform at 20 - 65℃; for 4h; Large scale;
Stage #2: In water Temperature; Large scale;
99.5%
bismuth(III) oxychloride at 20℃; for 0.0833333h;98%
zirconium(IV) oxychloride at 20℃; for 0.0833333h;97%
acetic anhydride
108-24-7

acetic anhydride

recorcinol
108-46-3

recorcinol

Resorcinol diacetate
108-58-7

Resorcinol diacetate

Conditions
ConditionsYield
With Sulfate; titanium(IV) oxide In dichloromethane at 40℃; for 0.0666667h;99%
With iron(III) p-toluenesulfonate hexahydrate In acetonitrile at 20℃; for 0.833333h;99%
With bismuth(lll) trifluoromethanesulfonate In acetonitrile at 20℃; for 0.166667h;98%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

recorcinol
108-46-3

recorcinol

1,3-dimesyloxybenzene
59722-31-5

1,3-dimesyloxybenzene

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 0 - 20℃; for 0.166667h; Green chemistry;99%
With pyridine
Benzotrichlorid
98-07-7

Benzotrichlorid

recorcinol
108-46-3

recorcinol

2,4-dihydroxybenzophenone
131-56-6

2,4-dihydroxybenzophenone

Conditions
ConditionsYield
With ethanol; water at 60 - 80℃; for 9h; Temperature; Green chemistry;99%
With water In ethanol at 40 - 50℃; for 4h; Temperature; Large scale;97.6%
With ethanol und Eintragen des Reaktionsgemisches in heisses Wasser;

108-46-3Related news

Insight into the mechanism of adsorption of phenol and Resorcinol (cas 108-46-3) on activated carbons with different oxidation degrees08/22/2019

In this work, activated carbons (ACs) with different oxidation degrees were fabricated and applied for phenol and resorcinol adsorption to systematically evaluate the adsorption mechanisms. The kinetics and isotherms at different temperatures were carried out to evaluate the adsorption rate and ...detailed

Environmental and occupational exposure to Resorcinol (cas 108-46-3) in Finland08/21/2019

Resorcinol is a suspected endocrine disruptor that affects thyroid function by inhibiting thyroxin peroxidase. It may also have an impact on iodine uptake. Resorcinol has various uses; for example in the manufacture of rubber products and in wood adhesives, flame retardants, UV stabilizers, and ...detailed

108-46-3Relevant articles and documents

-

Lock

, p. 1759,1764 (1933)

-

Deoxygenation of polyhydroxybenzenes: An alternative strategy for the benzene-free synthesis of aromatic chemicals

Hansen, Chad A.,Frost

, p. 5926 - 5927 (2002)

New synthetic connections have been established between glucose and aromatic chemicals such as pyrogallol, hydroquinone, and resorcinol. The centerpiece of this approach is the removal of one oxygen atom from 1,2,3,4-tetrahydroxybenzene, hydroxyhydroquinone, and phloroglucinol methyl ether to form pyrogallol, hydroquinone, and resorcinol, respectively. Deoxygenations are accomplished by Rh-catalyzed hydrogenation of the starting polyhydroxybenzenes followed by acid-catalyzed dehydration of putative dihydro intermediates. Pyrogallol synthesis consists of converting glucose into myo-inositol, oxidation to myo-2-inosose, dehydration to 1,2,3,4-tetrahydroxybenzene, and deoxygenation to form pyrogallol. Synthesis of pyrogallol via myo-2-inosose requires 4 enzyme-catalyzed and 2 chemical steps. For comparison, synthesis of pyrogallol from glucose via gallic acid intermediacy and the shikimate pathway requires at least 20 enzyme-catalyzed steps. A new benzene-free synthesis of hydroquinone employs conversion of glucose into 2-deoxy-scyllo-inosose, dehydration of this inosose to hydroxyhydroquinone, and subsequent deoxygenation to form hydroquinone. Synthesis of hydroquinone via 2-deoxy-scyllo-inosose requires 2 enzyme-catalyzed and 2 chemical steps. By contrast, synthesis of hydroquinone using the shikimate pathway and intermediacy of quinic acid requires 18 enzyme-catalyzed steps and 1 chemical step. Methylation of triacetic acid lactone, cyclization, and regioselective deoxygenation of phloroglucinol methyl ether affords resorcinol. Given the ability to synthesize triacetic acid lactone from glucose, this constitutes the first benzene-free route for the synthesis of resorcinol. Copyright

Synthetic Study on Acremoxanthone A: Construction of Bicyclo [32.2]nonane CD Skeleton and Fusion of AB Rings

Hirano, Yoichi,Tokudome, Kensei,Takikawa, Hiroshi,Suzuki, Keisuke

, p. 214 - 220 (2017)

Toward the total synthesis of acremoxanthone A, a model study has revealed a convergent approach to construct the ABCDE ring system. The key steps include: (1) an effective construction of the bicyclo[3.2.2]nonane skeleton, (2) protocol for generating the bridgehead anion and trapping, and (3) 1,3-dipolar cycloaddition of a nitrile oxide to the internal alkene.

Spectroscopy of hydrothermal reactions 23: The effect of OH substitution on the rates and mechanisms of decarboxylation of benzoic acid

Li, Jun,Brill, Thomas B.

, p. 2667 - 2673 (2003)

The decarboxylation rates of aqueous benzoic acid and 12 mono-, di-, and trihydroxy derivatives of benzoic acid were compared by using spectra from a flow reactor FTIR spectroscopy cell operating at 275 bar in the temperature range of 120-330 °C. Each compound was investigated at its natural pH and as the neutral acid (pH = 1.3-1.5). The decarboxylation reactions followed the first-order (or pseudo-first-order) rate law enabling the rate constants and corresponding Arrhenius parameters of the undissociated acids to be obtained. Based on the half-lives of the reactions at 200 °C, the thermal stability of the OH substituted benzoic acids follow the order: 2,4,6 > 2,4 > 2,3,4 > 2,6 > 2,5 > 2,3 > 3,4,5 > 2 > 3,4 > 4. Solutions of 3,5-dihydroxybenzoic and 3-hydroxybenzoic acids and unsubstituted benzoic acid had the highest thermal stability, whereas no decarboxylation was observed up to 330 °C at a residence time of about 45s. In general, the rate order is multiple ortho, para-OH substitution > ortho substitution > para substitution > meta substitution. The range of activation energies for the decarboxylation of OH substituted benzoic acids is 90-97 kJ/mol, and the rate differences are controlled mainly by activation entropy. The transition state structures were determined using density functional theory. Starting from the anti carboxylic hydrogen conformers in the gas phase, the activation energies to the transition state structures having the four-member C-C(O)-O-H ring are 213-260 kJ/mol using B3LYP/6-31G//B3LYP/6-31G and 202-246 kJ/mol using B3LYP/6-31+G(d,p)//B3LYP/6-31G(d). Incorporation of one water molecule forms a six-member cyclic structure, which dramatically reduces the activation energy by about 120-130 kJ/mol using B3LYP/6-31G//B3LYP/6-31G and by about 75 kJ/mol using B3LYP/6-31+G(d,p)//B3LYP/6-31G(d). In the water-catalyzed transition state structure, the water molecule acts as a bridge linked by two hydrogen bonds which enables concerted proton transfer and C-(CO2H) bond cleavage to occur. Although the calculated activation energy approximately follows the trend of the experimental half-lives, the experimental activation entropy appears to dominate in determining the rates.

-

Nunn,Rapson

, p. 3151,3155 (1949)

-

Ledwith,Woods

, p. 1422 (1970)

Chirikdjian et al.

, p. 1105 (1969)

Polymorphism in isomeric dihydroxybenzoic acids

Sarma, Bipul,Sanphui, Palash,Nangia, Ashwini

, p. 2388 - 2399 (2010)

Multifunctional molecules are capable of assembling via different supramolecular synthons, or hydrogen bond motifs, between the same or different functional groups, leading to the possibility of polymorphism. We have employed sublimation and melt crystallization to generate two new crystalline polymorphs of 3,5-dihydroxybenzoic acid (DHBA), and a second form for 2,3-dihydroxybenzoic acid and 3,4-dihydroxybenzoic acid each. Since hydroxybenzoic acids tend to give solvate/hydrate crystal structures by solution crystallization, solvent-free methods are necessary to obtain single crystals of unsolvated forms. In addition to guest-free polymorphs, a new hydrate polymorph of 3,4-dihydroxybenzoic acid was crystallized from cold water. Polymorphs of dihydroxybenzoic acids differ in the number of symmetry-independent molecules (Z'), the nature of the hydrogen bond synthon, the molecular packing, and the unit cell parameters. Structural and thermal characterization of polymorphic phases shows that the commercial material matches with the high Z' phase for 2,3-DHBA, 3,5-DHBA, and 3,4-DHBA hydrate even though a low Z' crystal structure is known in each case. Solventless crystallization conditions at high temperature are a practical method to generate new guest-free polymorphs and high Z' crystal structures for high affinity functional group compounds.

A {110} facet predominated Bi6O6(OH)3(NO3)3·1.5H2O photocatalyst: Selective hydrothermal synthesis and its superior photocatalytic activity for degradation of phenol

Yang, Li-Min,Zhang, Guo-Ying,Liu, Yue,Xu, Yan-Yan,Liu, Chun-Mei,Liu, Jing-Wang

, p. 79715 - 79723 (2015)

A basic bismuth(iii) nitrate photocatalyst with the composition of Bi6O6(OH)3(NO3)3·1.5H2O (BBN) was facilely synthesized using a hydrothermal strategy via incomplete hydrolysis of bismuth nitrate. Characterization of the composition, morphology, microstructure, optical absorption, BET surface area, and photocatalytic behavior was systematically explored. The results indicated that BBN architectures built up of multilayered meshing-teeth structures with predominant {110} side facets can be selectively obtained by fine-tuning the reaction parameters. The sample exhibits an obviously superior photocatalytic activity for the degradation of phenol compared with BBN sheets with dominant top {001} planes and commercial P25, with the rate constant k improved by 3.6 and 2.8 fold, respectively. The excellent photocatalytic behavior combined with the rather low BET surface area of 0.0453 m2 g-1 indicate that the highly reactive {110} facets in BBN are responsible for the photocatalysis. The active oxidation species and main intermediates in the phenol/BBN system are ascertained using scavenger experiments and high performance liquid chromatography (HPLC) techniques. Combining the band edge of BBN and the redox potentials of the active species, a possible migration mechanism of photogenerated e-/h+ pairs on the surface of BBN is proposed. This work provides some new insights for the rational design and synthesis of active-facet exposed basic salt photocatalysts with excellent efficiency.

Polyhedral Pt vs. spherical Pt nanoparticles on commercial titanias: Is shape tailoring a guarantee of achieving high activity?

Kovács,Fodor, Sz.,Vulpoi,Schrantz,Dombi,Hernádi,Danciu,Pap, Zs.,Baia

, p. 156 - 167 (2015)

As shape tailoring is gaining more attention in the field of photocatalysis, exploration of the impact of noble metal (Pt) nanoparticles' morphology on the activity of TiO2-Pt nanocomposites is inevitable. Spherical and polyhedral Pt nanoparticles have been synthesized by chemical reduction, while Aldrich anatase, Aldrich rutile, and Aeroxide P25 were used as base photocatalysts. The nanocomposites were analyzed using DRS, XRD, and HRTEM to uncover morphological, optical, and structural peculiarities of the composite photocatalysts. The importance of the Pt nanoparticles' geometry was proven at three levels: (i) UV light-driven photodegradation of three model pollutants: phenol, methyl orange, and oxalic acid; (ii) the primary degradation intermediates' evolution profile in the case of phenol degradation; and (iii) photocatalytic H2 production.

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Davis,Harrington

, p. 129,131 (1934)

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Black TiO2 nanotube arrays decorated with Ag nanoparticles for enhanced visible-light photocatalytic oxidation of salicylic acid

Plodinec, Milivoj,Gr?i?, Ivana,Willinger, Marc G.,Hammud, Adnan,Huang, Xing,Pan?i?, Ivana,Gajovi?, Andreja

, p. 883 - 896 (2019)

Novel forms of black TiO2 nanotubes-based photocatalysts for water purification were prepared. Two features were combined: decoration of TiO2 nanotube arrays with Ag nanoparticles (sample TiO2-NT's@Ag) and further hydrogenation of this material (TiO2-NT's@Ag-HA). Obtained photocatalysts show high efficiency for degradation of salicylic acid, a typical water-borne pollutant. The photocatalysts considerably exceed the photocatalytic properties of TiO2 nanotubes and commercial TiO2 P25 taken as a reference for modeling of the photocatalytic process. The comparison of photocatalytic activities between novel photocatalyst was based on a numerical approach supported by the complex kinetic model. This model allowed a separate study of different contributions on overall degradation rate. The contributions include: salicylic acid photolysis, photocatalysis in UVB, UVA and in the visible part of applied simulated solar irradiation. The superior photocatalytic performance of the photocatalyst TiO2-NT's@Ag-HA, particularly under visible irradiation, was explained by the combined effect of a local surface plasmon resonance (LSPR) due to Ag nanoparticles and creation of additional energy levels in band-gap of TiO2 due to Ti3+ states at nanotube surfaces. The presence of Ag also positively influence charge separation of created electron-holes pairs. The synergy of several effects was quantified by a complex kinetic model through the factor of synergy, fSyn. Stability testing indicated that the catalysts were stable for at least 20 h. The novel design of catalysts, attached on Ti foils, presents a solid base for the development of more efficient photocatalytic reactors for large-scale with a long-term activity.

Raney ni-al alloy mediated hydrodehalogenation and aromatic ring hydrogenation of halogenated phenols in aqueous medium

Liu, Guo-Bin,Zhao, Hong-Yun,Zhang, Jie,Thiemannb, Thies

, p. 342 - 344 (2009)

Raney Ni-Al alloy in a dilute aqueous alkaline solution has been shown to be a very powerful reducing agent and is highly effective for the reductive dehalogenation of polyhalogenated phenols and aromatic ring hydrogenation of phenols to the corresponding cyclohexanols.

Aqueous-phase hydrodeoxygenation of highly oxygenated aromatics on platinum

Yang, Jin,Williams, C. Luke,Ramasubramaniam, Ashwin,Dauenhauer, Paul J.

, p. 675 - 682 (2014)

Utilization of renewable sugars from biomass by a hybrid chemical process produces highly oxygenated aromatic compounds, such as phloroglucinol, which require catalytic reduction for desirable aromatic products. Aqueous phase hydrodeoxygenation of phloroglucinol on carbon-supported platinum produces resorcinol, phenol, cyclohexanol, cyclohexanone, and 1,3-cyclohexanediol by combinations of carbon-oxygen bond cleavage and carbon-carbon double bond hydrogenation. Carbon-carbon σ-bond cleavage was not observed. Hydrodeoxygenation was the primary reaction of phloroglucinol, leading to the production of resorcinol in the overall rate-limiting reaction, with an activation energy barrier of Ea = 117 kJ mol-1. Subsequent reactions of resorcinol produced 1,3-cyclohexanediol and phenol with similar energy barriers, Ea = 46 and Ea = 54 kJ mol-1, respectively. Further hydrogenation of phenol (Ea = 42 kJ mol -1) occurs through the intermediate, cyclohexanone, which is further reduced (Ea = 14 kJ mol-1) to the dominant product, cyclohexanol.

Copper phthalocyanine as an efficient and reusable heterogeneous catalyst for direct hydroxylation of benzene to phenol under mild conditions

Farahmand, Shohreh,Ghiaci, Mehran,Razavizadeh, Jala.S.

, p. 174 - 179 (2019)

The liquid-phase oxidation of benzene to phenol over copper phthalocyanine as a heterogeneous catalyst was studied at room temperature. Acetonitrile was chosen as the preferred solvent and hydrogen peroxide as an eco-friendly oxidant. The yield and selectivity of 13.9% and 100% were obtained, respectively. The catalyst was characterized by FT-IR, UV-Vis, XRD, TGA, XPS, 1H NMR, 13C NMR, CHN, BET, FE-SEM, TEM, and EDX analysis. The effects of different parameters on the catalytic performance of CuPc were also investigated. The reusability of the catalyst was studied, and the results showed that after five cycles the yield of phenol did not change noticeably, probably due to its stability in the reaction conditions.

Catalytic wet oxidation of phenol with Fe-ZSM-5 catalysts

Yan, Ying,Jiang, Songshan,Zhang, Huiping

, p. 3850 - 3859 (2016)

Fe-ZSM-5 and Fe2O3/ZSM-5 zeolite catalysts were prepared and tested for catalytic wet oxidation of phenol. First, Fe-ZSM-5 and Fe2O3/ZSM-5 zeolite catalysts were prepared by the hydrothermal synthetic and incipient wetness impregnation method and characterized to determine the framework and extra-framework Fe3+ species. Second, the catalytic properties of Fe-ZSM-5 in the oxidation of phenol were systematically studied to determine the optimum technological parameters by investigating the effects of reaction temperature, pH, catalyst concentration and stirring rate on the conversion of phenol. In addition to the phenol conversion, selectivity to CO2 and concentration of aromatic intermediates in the oxidation of phenol with the two catalysts were analyzed under the same optimum conditions. Leaching of iron from the catalysts, as well as the catalytic stability of Fe-ZSM-5, was also tested. Finally, the kinetics of catalytic wet oxidation of phenol with Fe-ZSM-5 was studied. The experimental results showed that both the framework and extra-framework Fe3+ species were present in Fe-ZSM-5. The oxidation reaction with Fe-ZSM-5 was performed well at a temperature of 70 °C, pH of 4, catalyst concentration of 2.5 g L-1, stirring rate of 400 rpm and reaction time of 180 min. The conversion of phenol reached 94.1%. From the catalytic results of the two catalysts, it can be concluded that the framework Fe3+ species may be more efficient in phenol oxidation than the extra-framework Fe3+ species, the stability of Fe-ZSM-5 was better and a relatively low decrease in activity could be found after three consecutive runs. The activation energy of 27.42 kJ mol-1 was obtained for phenol oxidation with Fe-ZSM-5.

Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide-Dimethyl Sulfoxide

Sang, Dayong,Tian, Juan,Tu, Xiaodong,He, Zhoujun,Yao, Ming

, p. 704 - 712 (2019)

Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o -hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.

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Petersen,Baehr-Predari

, p. 126 (1871)

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Study of the Reactivity of the [(PE1CE2P)Ni(II)] (E1, E2 = O, S) Pincer System with Acetonitrile and Base: Formation of Cyanomethyl and Amidocrotononitrile Complexes versus Ligand Decomposition by P-S Bond Activation

Hasche, Patrick,Spannenberg, Anke,Beweries, Torsten

, p. 4508 - 4515 (2019)

Nickel(II) chloride complexes with PE1CE2P (E = O, S) pincer ligands were used as precursors for the generation of cyanomethyl complexes in order to investigate the influence of variations (O vs S) in the side arms of the ligands on reactivity and stability of such compounds. In this regard, five hitherto unknown Ni(II) compounds were synthesized and fully characterized. Reaction of the Ni(II) chloride complex [(iPrPOCSPiPr)NiCl] (2-Cl) with 1 equiv of base and nitrile furnishes the cyanomethyl complex [(iPrPOCSPiPr)NiCH2CN] (2-CM). Increase of the amount of base and nitrile results in the formation of 3-amidocrotononitrile complexes [(iPrPOCOPiPr)NiNHC(CH3)CHCN] (1-ACN) and [(iPrPOCSPiPr)NiNHC(CH3)CHCN] (2-ACN). In contrast, similar reactions of the bis(thiophosphinite) complex 3-Cl resulted in formation of a tetranuclear Ni cluster (4) or a dinuclear 1,3-dithiolate-bridged PSCSP complex 5 by unexpected cleavage of P-S bonds of the pincer ligand.

Photocatalytic synthesis of phenols mediated by visible light using KI as catalyst

Huiqin, Wei,Wu, Mei

supporting information, (2021/11/30)

A transition-metal-free hydroxylation of iodoarenes to afford substituted phenols is described. The reaction is promoted by KI under white LED light irradiation and uses atmospheric oxygen as oxidant. By the use of triethylamine as base and solvent, the corresponding phenols are obtained in moderate to good yields. Mechanistic studies suggest that KI and catalysis synergistically promote the cleavage of C-I bond to form free aryl radicals.

Efficient demethylation of aromatic methyl ethers with HCl in water

Bomon, Jeroen,Bal, Mathias,Achar, Tapas Kumar,Sergeyev, Sergey,Wu, Xian,Wambacq, Ben,Lemière, Filip,Sels, Bert F.,Maes, Bert U. W.

supporting information, p. 1995 - 2009 (2021/03/26)

A green, efficient and cheap demethylation reaction of aromatic methyl ethers with mineral acid (HCl or H2SO4) as a catalyst in high temperature pressurized water provided the corresponding aromatic alcohols (phenols, catechols, pyrogallols) in high yield. 4-Propylguaiacol was chosen as a model, given the various applications of the 4-propylcatechol reaction product. This demethylation reaction could be easily scaled and biorenewable 4-propylguaiacol from wood and clove oil could also be applied as a feedstock. Greenness of the developed methodversusstate-of-the-art demethylation reactions was assessed by performing a quantitative and qualitative Green Metrics analysis. Versatility of the method was shown on a variety of aromatic methyl ethers containing (biorenewable) substrates, yielding up to 99% of the corresponding aromatic alcohols, in most cases just requiring simple extraction as work-up.

Isotruxene-based porous polymers as efficient and recyclable photocatalysts for visible-light induced metal-free oxidative organic transformations

Zhang, Haowen,Zhang, Xiao,Zheng, Ying,Zhou, Cen

supporting information, p. 8878 - 8885 (2021/11/27)

Two new isotruxene-based porous polymers were prepared and demonstrated to be highly efficient, metal-free heterogeneous photocatalysts for oxidative transformations using air as the mild oxidant under visible-light irradiation. Both catalysts show excellent recyclability. In addition, the reactions can be performed in water, further indicating the greenness of this method. This journal is

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