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Cas Database

100-51-6

100-51-6

Identification

  • Product Name:Benzyl alcohol

  • CAS Number: 100-51-6

  • EINECS:202-859-9

  • Molecular Weight:108.14

  • Molecular Formula: C7H8O

  • HS Code:2906.29

  • Mol File:100-51-6.mol

Synonyms:Benzyl alcohol (JP14/NF);Phenylmethyl alcohol;alpha-Hydroxytoluene;phenylcarbinol;Benzenecarbinol;.alpha.-Hydroxytoluene;(Hydroxymethyl)benzene;Phenylmethanol;Benzal alcohol;benzenemethanol;.alpha.-Toluenol;Methanol, phenyl-;Sunmorl BK 20;NCI-C06111;see Carbamo(dithioperox)imidic acid,phenylmethyl ester;Benzyl alcohol F.F.C.;Benzyl Alcohol , Natural;Benzyl alcohol nat.;benzoic alcohol;Benzyl Alcohol, Reagent;Phenolcarbinol;Phenyl Methanol;FEMA No. 2137;alpha-Toluenol;Benzyl Alcohol Natural;BenzylAlcohol(PhenylCarbinol);

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn,ToxicT

  • Hazard Codes:Xn,T

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH332 Harmful if inhaled

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Remove contaminated clothes. First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Refer for medical attention . Inhalation of vapor may cause irritation of upper respiratory tract. Prolonged or excessive inhalation may result in headache, nausea, vomiting, and diarrhea. In severe cases, respiratory stimulation followed by respiratory and muscular paralysis, convulsions, narcosis and death may result. Ingestion may produce severe irritation of the gastrointestinal tract, followed by nausea, vomiting, cramps and diarrhea; tissue ulceration may result. Contact with eyes causes local irritation. Material can be absorbed through skin with anesthetic or irritant effect. (USCG, 1999) Enhancement of elimination: Hemodialysis may enhance the elimination of benzyl alcohol and its metabolites and may also be useful to help correct severe metabolic acidosis. However, more cases involve prolonged repeated infusion, and the usefulness of dialysis in unknown.

  • Fire-fighting measures: Suitable extinguishing media Foam, carbon dioxide, dry chem ... This chemical is combustible. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from strong oxidants.Benzyl alcohol is stored in stainless steel tanks. Because benzyl alcohol oxidizes readily, it is advisable to cover the surface of the liquid with nitrogen.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:Benzyl Alcohol
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  • Product Description:Benzyl Alcohol min. 99.0 %
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Relevant articles and documentsAll total 1936 Articles be found

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.

Nitrous Oxide as a Nucleophile in the Formation of a New Reactive Intermediate from Benzyl Cations in the Solvolysis of Benzyl Azoxytosylate

Maskill, H.,Jencks, William P.

, p. 944 - 946 (1984)

Rate and product analytical results of solvolysis of benzyl azoxytosylate in 1:1 (v/v) trifluoroethanol : water require two product-forming routes: one involves a long-lived intermediate (formed from benzyl cations and nitrous oxide) which is trappable by

-

Gaylord,Kay

, p. 1574 (1958)

-

Reactivity of silole within a core-modified porphyrin environment: Synthesis of 21-silaphlorin and its conversion to carbacorrole

Skonieczny, Janusz,Latos-Grazynski, Lechoslaw,Szterenberg, Ludmila

, p. 4861 - 4874 (2008)

Condensation of 1,1-dimethyl-3,4-diphenyl-2,5-bis(p-tolylhydroxymethyl) silole with pyrrole and p-tolylaldehyde did not form the expected 21,21-dimethyl-2,3-diphenyl-5,10,15,20-tetra(p-tolyl)-21 -silaporphy rin, but rather its reduced derivative, 21-silap

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-).

Novel preparation of 2,1-benzothiazine derivatives from sulfonamides with [hydroxy(tosyloxy)iodo]arenes

Misu, Yuhta,Togo, Hideo

, p. 1342 - 1346 (2003)

Cyclization of sulfonamides bearing an aromatic ring at the β-position with various organohypervalent iodine compounds was carried out to form the corresponding 2,1-benzothiazine derivatives. Among them, the cyclization effectively proceeded with [hydroxy

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.

Oxidation of toluene in NOx free air: product distribution and mechanism

Seuwen, P.,Warneck, P.

, p. 315 - 332 (1996)

Product distributuion resulting from the oxidation in air initiated by chlorine atoms, by toluene photolysis, and by hydroxyl radicals were studied at atmospheric pressure in the absence of nitrogen oxides.In the first case only benzaldehyde and benzylalcohol with a ratio of 7.8 +/- 1.7 were observed, from wich a branching ratio α = 0.76 +/- 0.05 was derived for the radical propagating pathway of the self-reaction of benzylperoxy radicals.In the second and third case the apparent branching ratio decreased to α = 0.56 +/- 0.07 and 0.37 +/- 0.08, respectively, indicating the occurence of additional reactions between benzylperoxy and other peroxy radicals.The major ring retaining products resulting from the reaction of OH with toluene were o-cresol, p-cresol, and methyl-p-benzo-quinone (57.9 +/- 12.5percent reacted carbon, corrected for secondary losses), in addition to 7.7 +/- 1.6percent benzaldehyde and benzylalcohol arising from methyl hydrogen abstraction.Formaldehyde, acetaldehyde, glyoxal, methylglyoxal, carbon monoxide, and carbon dioxide were observed as ring cleavage products (25.0 +/- 7.2percent).Except for CO2, which appears to be an important ring cleavage product only under NOx-free conditions, the distribution of ring cleavage products was similar to that found by Gery et al. (1985) in the presence of NOx.Comparison of experimental data and results from computer simulations show that self-reactions of the hydroxy-methyl-cyclo-hexadienylperoxy radicals are negligible compared to internal rearrangement reactions leading to ring stabilization or ring cleavage.The mechanisms of CO2 production appears to require the formation of a Criegee intermediate.

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

Solvent-free reduction of carboxylic acids to alcohols with NaBH4 promoted by 2,4,6-trichloro-1,3,5-triazine and PPh3 in the presence of K2CO3

Jaita, Subin,Kaewkum, Pantitra,Duangkamol, Chuthamat,Phakhodee, Wong,Pattarawarapan, Mookda

, p. 46947 - 46950 (2014)

A simple, rapid, and eco-friendly method for NaBH4 reduction of carboxylic acids to alcohols under solvent-free conditions was developed using a combination of 2,4,6-trichloro-1,3,5-triazine (TCT) with a catalytic amount of triphenylphosphine as an acid activator. With the 1 : 0.2 : 1.5 : 2 mole ratio of TCT : PPh3 : K2CO3 : NaBH4, carboxylic acids including aromatic acids, aliphatic acids, and N-protected α-amino acids (Fmoc, Z) could readily undergo reduction to give the corresponding alcohols in good to excellent yields within 10 min.

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.

Synthesis of β-hydroxy-α,α-disubstituted amino acids through the orthoamide-type overman rearrangement of an α,β-unsaturated ester and stereodivergent intramolecular SN2′ reaction: Development and application to the total synthesis of sphingofungin F

Sugai, Tomoya,Usui, Shunme,Tsuzaki, Shun,Oishi, Hiroki,Yasushima, Daichi,Hisada, Shoko,Fukuyasu, Takahiro,Oishi, Takeshi,Sato, Takaaki,Chida, Noritaka

, p. 594 - 607 (2018)

The development of a two-step synthesis for β-hydroxy-α,α- disubstituted amino acid derivatives from cyclic orthoamide is reported. The first step is the orthoamide-type Overman rearrangement of an α,β-unsaturated ester to give a sterically hindered α,α-disubstituted amidoester. The α,β-unsaturated ester is known to be a challenging substrate in the conventional Overman rearrangement due to the competitive aza-Michael reaction. However, suppression of the aza-Michael reaction is realized by two factors; 1) the high reaction temperature, and 2) an alkyl substituent at the α-position. The second step is stereodivergent intramolecular SN2′ reaction for the installation of a hydroxy group at the β-position. Either syn- or anti-type SN2′ reaction is possible by simply changing the reaction conditions. The developed method can provide all four possible stereoisomers of the β-hydroxy-α,α-disubstituted amino acid, and is successfully applied to the total synthesis of sphingofungin F.

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

-

Chaudhari, F. M.,Knox, G. R.,Pauson, P. L.

, (1967)

-

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,.

-

Maki et al.

, p. 3295 (1975)

-

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.

-

Dyer,Newborn

, p. 5495,5496,5498 (1958)

-

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.

Cobalt-Catalyzed Reductive Alkylation of Amines with Carboxylic Acids

Emayavaramban, Balakumar,Chakraborty, Priyanka,Sundararaju, Basker

, p. 3089 - 3093 (2019)

Direct reductive alkylation of amines with carboxylic acid is carried out by using an inexpensive, air-stable cobalt/triphos catalytic system with molecular hydrogen as the reductant. This efficient synthetic method proceeds through reduction and condensation, followed by reduction of the in situ-generated imine into the amine in a green catalytic process.

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

THE GAS-PHASE REDUCTIVE DIMERIZATION OF BENZALDEHYDE ON A FUSED IRON CATALYST

Glebov, L. S.,Shuikin, A. N.,Kliger, G. A.,Mikaya, A. I.,Zaikin, V. G.,et al.

, p. 814 - 817 (1990)

The gas-phase heterogeneous catalytic reductive dimerization of benzaldehyde to trans-stilbene and dibenzyl was carried out on a reduced promoted fused iron catalyst.The mechanism of this reaction was examined.

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.

Variations on an NHC theme: Which features enhance catalytic transfer hydrogenation with ruthenium complexes?

Depasquale, Joseph,Kumar, Mukesh,Zeller, Matthias,Papish, Elizabeth T.

, p. 966 - 979 (2013)

N-heterocyclic carbene (NHC) based ruthenium complexes were studied as catalysts for the transfer hydrogenation of ketones. Variations in the catalyst structure were investigated for their impact on hydrogenation and catalyst stability. Catalyst attributes included bis- or mono-NHC ligands, pendant ether groups in some cases, and arene ligands of varied bulk and donor strength. Ruthenium complexes were synthesized and fully characterized, including complexes with a monodentate NHC ligand containing a tethered ether N substituent (ImEt,CH2CH2OEtRuCl2(η6-arene); arene = benzene (4), p-cymene (5), hexamethylbenzene (6)), a complex with a monodentate NHC ligand with solely alkyl N substituents (Im Et,PentylRuCl2(η6-p-cymene) (8)), and a complex with a bis-NHC ligand ([RuCl(methylenebis(ImEt) 2)(η6-p-cymene)]PF6 (7)) (Im = imidazole-derived NHC; superscripts indicate N substituents). X-ray crystal structures were obtained for 4, 5, 7, and 8. All of the ruthenium complexes were tested and found to be active transfer hydrogenation catalysts for the reduction of acetophenone to 1-phenylethanol in basic 2-propanol. Precatalyst 4, which contains a tethered ether group and benzene ligand, was found to be the most active catalyst. Variable-temperature 1H NMR studies of complexes 4-6 show that arene lability increases in the order C 6Me6 -1 and 845, respectively, for ketone reduction with catalyst 4.

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.

HOMOGENEOUS HYDROGENATION OF KETONES USING CHROMIUM HEXACARBONYL AS CATALYST PRECURSOR IN THE PRESENCE OF BASES

Marko, Laszlo,Nagy-Magos, Zsuzsa

, p. 193 - 204 (1985)

The hydrogenation of ketones at 100-120 degC and 100 bar H2 is catalyzed by Cr(CO)6 in methanol solution in the presence of NaOMe.The reaction is inhibited by CO and the rate increases with increasing H2 pressure and base: chromium ratio.In a stoichiometric reaction at 75 degC, HCr(CO)5- hydrogenates ketones to alcohols, while forming Cr2(CO)102-.A catalytic cycle involving alkoxychromium complexes, R2CHOCr(CO)5-, as intermediates is proposed.Similar hydrogenation catalysts are obtained from W(CO)6 and Mo(CO)6; the latter is the most active and may be used even at 70-80 degC.

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.

A highly active worm-like PtMo nanowire for the selective synthesis of dibenzylamines

Lu, Shuanglong,Xu, Pengyao,Cao, Xueqin,Gu, Hongwei

, p. 8755 - 8760 (2018)

Worm-like nanowires are among the most active nanomaterials. In this study, we report the synthesis of dibenzylamine (DBA) motifs from reductive amination of either aldehydes or nitriles catalyzed by entirely new worm-like PtMo nanowires (PtMo WNWs). Under the assistance of H2 gas, PtMo WNWs can be prepared in a facile manner, following which, their structure and composition are characterized by TEM, XRD, XPS, etc. Upon careful optimization of reaction parameters, the as-prepared PtMo WNWs work effectively in the activation of dihydrogen molecules, and both aldehydes and nitriles can be used as starting materials to fabricate DBAs under mild and green conditions. The reaction kinetics has been investigated, which reveals that the PtMo WNWs show superior activity in the conversion of imines into amines. This study provides a practical advancement in the preparation of amines. Moreover, the protocol reported herein is feasible for the synthesis of worm-like nanostructures with designed composition for various catalytic applications.

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.

Interfacial CoOx Layers on TiO2 as an Efficient Catalyst for Solvent-Free Aerobic Oxidation of Hydrocarbons

Wang, Hai,Wang, Liang,Zhang, Jian,Wang, Chengtao,Liu, Ziyu,Gao, Xinhua,Meng, Xiangju,Yoo, Seung Jo,Kim, Jin-Gyu,Zhang, Wei,Xiao, Feng-Shou

, p. 3965 - 3974 (2018)

Construction of efficient interfaces to improve the performance of supported metal catalysts is a challenging but effective technique. A newly synthesized catalyst with layered cobalt oxide on the surface of titania (layer-CoOx/TiO2) is highly selective towards the aerobic oxidation of C?H bonds in a series of hydrocarbons under sustainable conditions. The layer-CoOx/TiO2 easily outperforms the state-of-the-art noble metal catalysts and homogeneous cobalt salts used in industry. In-depth structural and functional characterization reveal that the layer-CoOx/TiO2 readily reacts with O2 for the adsorption and activation of C?H bonds. The layered structure of CoOx can maximize the interfacial effect of CoOx/TiO2 leading to a good performance for the oxidation of C?H bonds.

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

Tetrahydropyranylation of alcohols and phenols using polystyrene supported lewis acids as catalysts

Zhang, Yi,Dou, Qianqian,Liu, Yuan,Dai, Liyan,Wang, Xiaozhong,Chen, Yingqi

, p. 2567 - 2572 (2012)

Polystyrene supported TiCl4 (Ps-TiCl4) and polystyrene supported FeCl3(Ps-FeCl3) were prepared by coordinating Lewis acids with polystyrene. The catalysts were characterized by TGA, BET, SEM, IR and pyridine-adsorbed IR. The loading of Ps-TiCl4 and Ps-FeCl3 were 0.35 and 0.3 mmol·g-1 respectively. Both catalysts were found to be efficient for the tetrahydropyranylation and detetrahydropyranylation of various alcohols and phenols in different solvents. Two catalysts can be recovered and reused for five times with good activity. Polystyrene supported TiCl4 (Ps-TiCl4) and polystyrene supported FeCl3(Ps-FeCl 3) were prepared by coordinating Lewis acids with polystyrene. The catalysts were characterized by TGA, BET, SEM, IR and pyridine-adsorbed IR. The loading of Ps-TiCl4 and Ps-FeCl3 were 0.35 and 0.3 mmol·g-1 respectively. Both catalysts were found to be efficient for the tetrahydropyranylation and detetrahydropyranylation of various alcohols and phenols in different solvents. Two catalysts can be recovered and reused for five times with good activity. Copyright

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.

-

Hauser,Kantor

, p. 1437,1441 (1951)

-

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.

OXIDATIVE Si-C BOND CLEAVAGE OF ORGANOTRIFLUOROSILANES INVOLVING ORGANIC-GROUP MIGRATION FROM HYPERCOORDINATE SILICON TO OXYGEN

Sato, Kazuhiko,Kira, Mitsuo,Sakurai, Hideki

, p. 4375 - 4378 (1989)

Various organotrifluorosilanes react with trimethylamine-N-oxide without catalyst to give the corresponding alcohols in high yields under mild conditions.Stereospecific nature of the reaction is suggestive of the involvment of intramolecular 1,2-organic-group migration from hypercoordinate silicon to oxygen.

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

A desilylation and a one-pot desilylation-oxidation of aliphatic tert-butyldimethylsilyl ethers using catalytic quantities of PdCl2(CH3CN)2

Wilson, Noel S.,Keay, Brian A.

, p. 2918 - 2919 (1996)

-

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.

Transformation of benzonitrile into benzyl alcohol and benzoate esters in supercritical alcohols

Kamitanaka, Takashi,Yamamoto, Kenji,Matsuda, Tomoko,Harada, Tadao

, p. 5699 - 5702 (2008)

The reactions of benzonitrile in supercritical methanol, ethanol, and 2-propanol were investigated under non-catalytic conditions. In supercritical methanol, benzonitrile was converted to methyl benzoate in high yield. The esterification reaction also occurred in supercritical ethanol to afford ethyl benzoate in moderate yield. The esterification could occur via a route analogous to the Pinner reaction. On the other hand, benzonitrile in supercritical 2-propanol yielded no ester. Benzyl alcohol was the major product in supercritical 2-propanol. We investigated the reaction of the C{double bond, long}N bond in supercritical 2-propanol. In supercritical 2-propanol, N-benzylideneaniline was transferred to the reduction product (N-benzylaniline) and hydrolysis products (benzyl alcohol and aniline). The hydrolysis reaction was restricted when the reaction was carried out in supercritical 2-propanol with a low water content. This indicates that the water in the 2-propanol acts as a reagent for the hydrolysis of the C{double bond, long}N bond. These results suggested the following reaction process: C6H5C{triple bond, long}N→C6H5CH{double bond, long}NH→C6H5CHO→C6H5CH2OH.

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.

-

Swamer,Hauser

, p. 2647 (1946)

-

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

Non-Pincer-Type Manganese Complexes as Efficient Catalysts for the Hydrogenation of Esters

van Putten, Robbert,Uslamin, Evgeny A.,Garbe, Marcel,Liu, Chong,Gonzalez-de-Castro, Angela,Lutz, Martin,Junge, Kathrin,Hensen, Emiel J. M.,Beller, Matthias,Lefort, Laurent,Pidko, Evgeny A.

, p. 7531 - 7534 (2017)

Catalytic hydrogenation of carboxylic acid esters is essential for the green production of pharmaceuticals, fragrances, and fine chemicals. Herein, we report the efficient hydrogenation of esters with manganese catalysts based on simple bidentate aminophosphine ligands. Monoligated Mn PN complexes are particularly active for the conversion of esters into the corresponding alcohols at Mn concentrations as low as 0.2 mol % in the presence of sub-stoichiometric amounts of KOtBu base.

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.

Cu and boron doped carbon nitride for highly selective oxidation of toluene to benzaldehyde

Han, Hongling,Ding, Guodong,Wu, Tianbin,Yang, Dexin,Jiang, Tao,Han, Buxing

, p. 12686 - 12697 (2015)

A novel Cu and boron doped graphitic carbon nitride catalyst (Cu-CNB) was synthesized using cheap precursors and systematically characterized. The selective oxidation of toluene proceeded very smoothly over the catalyst at 70 °C using tert-butyl hydropero

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.

ORGANOCERIUM REAGENTS FROM IODINE ACTIVATED CERIUM METAL AND ORGANIC IODIDES: THEIR REACTIONS WITH CARBONYL COMPOUNDS

Fukuzawa, Shin-ichi,Fujinami, Tatsuo,Sakai, Shizuyoshi

, p. 179 - 186 (1986)

Cerium metal activated by a trace of iodine reacted smoothly with alkyl, allyl, and aryl iodides to give the corresponding organocerium reagents.The reaction of the organocerium reagents thus prepared in situ with carbonyl compounds gave not only Grignard-type adducts but also reduction and reductive coupling products.

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.

α-Deuterium Isotope Effects in Benzyl Halides. 2. Reaction of Nucleophiles with Substituted Benzyl Bromides. Evidence for a Change in Transition-State Structure with Electron-Donating Substituents

Vitullo, V.P.,Grabowski, J.,Sridharan, S.

, p. 6463 - 6465 (1980)

Rates and α-D isotope effects have been determined for the following substrates and nucleophiles: p-methoxybenzyl bromide (Et3N, SCN-, N3-, OH-, S2O32-) benzyl bromide (Et3N, SCN-, N3-, OH-, S2O32-), and p-nitrobenzyl bromide (Et3N, SCN-, N3-, S2O32-).In nearly all cases the second-order rate constant for each nucleophile goes though a minimum for the unsubstituted compound while the α-D isotope increases monotonically in the sequence p-NO2>p-H>p-OCH3.These results are consistent with an increasing "looseness" of the SN2 transition state as the substituent on the aromatic ring becomes more electron donating.

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.).

Selective catalytic synthesis of bio-based high value chemical of benzoic acid from xylan with Co2MnO4@MCM-41 catalyst

Fan, Minghui,He, Yuting,Li, Quanxin,Luo, Yuehui,Yang, Mingyu,Zhang, Yanhua,Zhu, Lijuan

, (2021/12/20)

The efficient synthesis of bio-based chemicals using renewable carbon resources is of great significance to promote sustainable chemistry and develop green economy. This work aims to demonstrate that benzoic acid, an important high added value chemical in petrochemical industry, can be selectively synthesized using xylan (a typical model compound of hemicellulose). This novel controllable transformation process was achieved by selective catalytic pyrolysis of xylan and subsequent catalytic oxidation. The highest benzoic acid selectivity of 88.3 % with 90.5 % conversion was obtained using the 10wt%Co2MnO4@MCM-41 catalyst under the optimized reaction conditions (80 °C, 4 h). Based on the study of the model compounds and catalyst's characterizations, the reaction pathways for the catalytic transformation of xylan to bio-based benzoic acid were proposed.

3D structured TiO2-based aerogel photocatalyst for the high-efficiency degradation of toluene gas

Dai, Li,Guan, Jie,Li, Shijie,Li, Xueying,Yu, Wei,Zhang, Li

, p. 2272 - 2281 (2022/02/16)

Photocatalytic technology is a green , environmentally friendly, energy-saving technology, which is considered to be an ideal method for removing volatile organic compounds (VOCs). At present, photocatalytic technology mostly uses powdered catalysts, which is not conducive to recycling and restricts the contact between the gas and catalyst. In this work, a three-dimensional (3D)-structured TiO2-based aerogel with TiO2 as the main body and all the components beneficial to photocatalysis was prepared for the first time. Under simulated sunlight irradiation, the toluene-removal rate of the Pt-loaded TiO2 and reduced graphene oxide (RGO) composite aerogel (denoted as Pt-TiO2/RGO aerogel, or PTA thereafter) was 60.47% higher than that of the pure RGO aerogel, and 56.03% higher than that of the bare TiO2 nanofibers. The block-shaped composite aerogel could be easily recycled, and the C/C0 of toluene using the recycled sample decreased by only 5.31% in the 5th run. The Pt-TiO2/RGO composite aerogel had the highest photocatalytic degradation rate of toluene with a relative humidity (RH) of 60-80%, which is conducive to the purification of VOCs in high-humidity areas. The 3D aerogel enriches the contact between the solid photocatalyst and the toluene molecules, and also solves the problem of low adhesion between the catalyst and the carrier. This work provides a new perspective for the efficient removal of toluene gas by constructing a highly active 3D TiO2 aerogel with an increased gas-solid reaction rate.

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.

Supported Iridium Catalyst for Clean Transfer Hydrogenation of Aldehydes and Ketones using Methanol as Hydrogen Source

He, Guangke,Liu, Xiang,Wang, Jing,Ye, Sen,Zhu, Jiazheng,Zhu, Longfei

, (2022/02/01)

The use of methanol as abundant and low-toxic hydrogen source under mild and clean conditions is promising for the development of safe and sustainable reduction processes, but remains a daunting challenge. This work presents a recyclable ZnO-supported Ir

Process route upstream and downstream products

Process route

phosgene
75-44-5

phosgene

diethyl ether
60-29-7,927820-24-4

diethyl ether

2-ClC<sub>6</sub>H<sub>4</sub>CH<sub>2</sub>OBn
52322-07-3

2-ClC6H4CH2OBn

isopropylmagnesium bromide
920-39-8

isopropylmagnesium bromide

2-Chlorobenzyl alcohol
17849-38-6

2-Chlorobenzyl alcohol

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
diethyl ether
60-29-7,927820-24-4

diethyl ether

methylmagnesium iodide

methylmagnesium iodide

benzaldehyde
100-52-7

benzaldehyde

1-Phenylethanol
98-85-1,13323-81-4

1-Phenylethanol

benzalacetophenone
94-41-7

benzalacetophenone

acetophenone
98-86-2

acetophenone

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
Erwaermen des Reaktionsprodukts mit Benzaldehyd und nach Zersetzung mit verd.Schwefelsaeure;Produkt5: Dibenzoylmethan;
benzyl 4-(nitro)phenylcarbamate
53821-12-8

benzyl 4-(nitro)phenylcarbamate

ethanolamine
141-43-5

ethanolamine

4-Nitrophenyl isocyanate
100-28-7

4-Nitrophenyl isocyanate

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
at 130 - 170 ℃;
1-Phenylprop-1-yne
673-32-5

1-Phenylprop-1-yne

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

3-phenyl-2-propanol
698-87-3,14898-87-4

3-phenyl-2-propanol

1-Phenylethanol
98-85-1,13323-81-4

1-Phenylethanol

(RS)-2-phenyl-1-propanol
1123-85-9

(RS)-2-phenyl-1-propanol

(2E)-3-phenyl-2-propen-1-ol
4407-36-7

(2E)-3-phenyl-2-propen-1-ol

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With lithium aluminium tetrahydride; oxygen; at 80 ℃; for 61h; under 759.8 Torr; Product distribution; autoxidation;
5 % Turnov.
1.4 % Turnov.
56.7 % Turnov.
29.9 % Turnov.
1.1 % Turnov.
5.9 % Turnov.
methyl chlorobenzoate
610-96-8

methyl chlorobenzoate

benzoic acid methyl ester
93-58-3,5705-52-2,80226-58-0

benzoic acid methyl ester

2-Chlorobenzyl alcohol
17849-38-6

2-Chlorobenzyl alcohol

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With samarium diiodide; water; In pyridine; for 0.00833333h; Ambient temperature;
13%
23%
53%
With samarium diiodide; water; In tetrahydrofuran; for 0.00833333h; Ambient temperature;
53%
13%
23%
2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

benzyl tosylate
1024-41-5

benzyl tosylate

((2,2,2-trifluoroethoxy)methyl)benzene
67696-28-0

((2,2,2-trifluoroethoxy)methyl)benzene

benzyl bromide
100-39-0

benzyl bromide

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With water; sodium bromide; at 25 ℃; Rate constant;
N-Nitroso-N-benzylformamide
85995-49-9

N-Nitroso-N-benzylformamide

phenylmagnesium bromide

phenylmagnesium bromide

phenyl benzyl ketone
451-40-1

phenyl benzyl ketone

1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

benzyl bromide
100-39-0

benzyl bromide

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With water; In diethyl ether; Product distribution; Mechanism; Ambient temperature;
methylmagnesium bromide
75-16-1

methylmagnesium bromide

benzaldehyde
100-52-7

benzaldehyde

1-Phenylethanol
98-85-1,13323-81-4

1-Phenylethanol

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With titanium (2R,3R)-2,3-(isopropylidenedioxy)butane-1,4-dioxide diisopropoxide; multistep reaction; other alkyl- and aralkyl magnesium halides, aldehyde and reagent;
benzaldehyde
100-52-7

benzaldehyde

acetophenone
98-86-2

acetophenone

1-Phenylethanol
98-85-1,13323-81-4

1-Phenylethanol

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With sodium tetrahydroborate; tin(ll) chloride; In tetrahydrofuran; for 1.5h; Heating; selectivity, absence of SnCl2, further solvents;
96.8%
8%
With 5-ethyl-2-methylpyridine borane complex; acetic acid; at 20 - 70 ℃; for 0.0833333h; Product distribution / selectivity;
With C38H52ClIrN2O2; potassium hydroxide; In isopropyl alcohol; at 85 ℃; for 5h; Temperature; Inert atmosphere;
With sodium tetrahydroborate; In water; at 20 ℃; for 1h;
With {(Mo(CO)3(NCMe)(η4-C4Ph4CO))}; In benzene-d6; isopropyl alcohol; at 65 ℃; for 1h; Kinetics;
benzaldehyde
100-52-7

benzaldehyde

1,1-dibromomethane
74-95-3

1,1-dibromomethane

1-Phenylethanol
98-85-1,13323-81-4

1-Phenylethanol

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With lithium; In tetrahydrofuran; Ambient temperature;

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