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Cas Database

103-82-2

103-82-2

Identification

  • Product Name:Phenylacetic acid

  • CAS Number: 103-82-2

  • EINECS:203-148-6

  • Molecular Weight:136.15

  • Molecular Formula: C8H8O2

  • HS Code:2916.33

  • Mol File:103-82-2.mol

Synonyms:Aceticacid, phenyl- (6CI,8CI);2-Phenylacetic acid;NSC 125718;PAA;Phenylaceticacid;Phenylethanoic acid;a-Toluic acid;w-Phenylacetic acid;Benzeneacetic acid;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H319 Causes serious eye irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. In case of skin contact Rinse skin with plenty of water or shower. 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. Give one or two glasses of water to drink. Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Powder, water spray, foam, carbon dioxide. 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. Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. Personal protection: A/P2 filter respirator for organic vapor and harmful dust. Do NOT let this chemical enter the environment. Sweep spilled substance into containers.

  • 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, strong bases and strong reducing agents. Store in an area without drain or sewer access.Separated from strong oxidants, strong bases and strong reducing agents. Store in an area without drain or sewer access.

  • 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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Relevant articles and documentsAll total 599 Articles be found

Synthesis, crystal structure of Co(II)(6-methoxybenzothiazole-2-carboxylate)2(DMF)2 and its application to carbonylation of benzyl chloride

Zhang, Bin,Li, Jianli,Chen, Wei,Wang, Yunxia,Shi, Zhen

, p. 111 - 114 (2010)

A new complex, Co(MBTC)2(DMF)2 (MBTC(6-methoxybenzothiazole-2-carboxylate, DMF=N,N-dimethylformamide), was synthesized in DMF solution and characterized by single crystal X-ray diffraction analysis. Using the cobalt complex as catalyst, phenylacetic acid was prepared by the carbonylation of benzyl chloride with carbon monoxide (0.1 MPa). The effects of solvents, phase transfer catalysts and temperature on the reactions were investigated. The yield of phenylacetic acid was higher than 90% in optimized condition.

Lanthanide-Promoted and Nickel Cyanide Catalyzed Carbonylation Reactions under Phase-Transfer Conditions

Amer, Ibrahim,Alper, Howard

, p. 927 - 930 (1989)

The nickel cyanide and phase transfer catalyzed carbonylation of benzyl chlorides is promoted by lanthanide salts .This simple reaction is sensitive to the concentration of the lanthanide compound, sodium hydroxide, quaternary ammonium salt, and nickel catalyst.The nature of the organic phase and phase transfer agent also influences the reaction rate.The acceleration of the reaction may be a consequence of coordination of a nickel cyanide nitrogen lone pair to the lanthanide salt.

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Wenkert,E.,McPherson,C.A.

, p. 8084 - 8090 (1972)

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Photoreactivity of 1-Pyrenylmethyl Esters. Dependence on the Structure of the Carboxylic Acid Moieties and the Nature of the Excited States

Iwamura, Michiko,Tokuda, Kazuko,Koga, Noboru,Iwamura, Hiizu

, p. 1729 - 1732 (1987)

While the photolysis of 1-pyrenylmethyl phenylacetates in methanol gave the original phenylacetic acids, irradation of the 1-naphthoate and 9-anthracenecarboxylate leads to the formation of the intramolecular exciplexes that are inert to the photolysis.The Φf and τf values of these esters have been determined.

Penicillin G amidase-catalysed hydrolysis of phenylacetic hydrazides on a solid phase: A new route to enzyme-cleavable linkers

Basso, Alessandra,Ebert, Cynthia,Gardossi, Lucia,Linda, Paolo,Phuong, Thao Tran,Zhu, Mingzhao,Wessjohann, Ludger

, p. 963 - 966 (2005)

A novel catalytic property of penicillin G amidase (PGA) is described. Unexpectedly, the enzyme can hydrolyse hydrazide bonds with good efficiency, and in solution the enzyme shows a selectivity that is similar to phenylacetamides. The hydrolysis of phenylacetic hydrazides releases hydrazine, but no inhibition due to the formation of such reactive compounds was observed. This novel catalytic property was assayed also on a solid phase as a pioneering route for the design of enzyme-cleavable linkers and masked scavengers for ketones. On a solid phase a phenylacetic hydrazide compound was chemically synthesised on PEGA1900 and PEGA+ (two co-polymers of acrylamide and ethylene glycol) and the efficiency of PGA in the release of phenylacetic acid depended on the diffusion of the protein inside the polymer. On PEGA+ the enzyme, as previously described, shows a good diffusion due to an improved electrostatic interaction with PGA thus achieving good hydrolytic conversions.

Microwave-assisted rapid hydrolysis and preparation of thioamides by Willgerodt-Kindler reaction

Matloubi Moghaddam,Ghaffarzadeh

, p. 317 - 321 (2001)

Aldehydes and aryl alkyl ketones were efficiently transformed to thioamides with the same number of carbon atoms via Willgerodt-Kindler reaction under microwave irradiation in solvent-free conditions. The thioamides obtained were hydrolyzed to corresponding carboxylic acids with microwave dielectric heating in one minute. Both reactions are very fast and the yields are excellent.

Copper-catalysed Reaction of Arylacetylenes with C,N-Diarylnitrones

Okuro, Kazumi,Enna, Masahiro,Miura, Masahiro,Nomura, Masakatsu

, p. 1107 - 1108 (1993)

Reaction of arylacetylenes with C,N-diarylnitrones is effectively catalysed by copper(I) iodide-dppe in the presence of potassium carbonate to give the corresponding 1-azabut-1-en-3-yne (iminopropyne) derivatives in good yield.

Preparation of Protein Conjugates via Homobifunctional Diselenoester Cross-Linker

Yin, Xu-Guang,Gao, Xiao-Fei,Du, Jing-Jing,Zhang, Xiao-Kang,Chen, Xiang-Zhao,Wang, Jian,Xin, Ling-Ming,Lei, Ze,Liu, Zheng,Guo, Jun

, p. 5796 - 5799 (2016)

Adipic acid diselenoester was developed as an efficient cross-linker for covalent protein conjugation with a variety of small molecular haptens, including mono- and disaccharides, peptide, fluorescence dye, and nicotine. Compared to the counterparts of N-hydroxysuccinimide (NHS) and p-nitrophenyl (PNP) linkers, the diselenoester linker demonstrates improved balance between reactivity and stability and coupling of haptens to proteins under mild conditions with high incorporation efficiency.

Cornforth

, p. 3933 (1974)

Permanganate Ion Oxidations. 14. Kinetics and Mechanism of the Oxidation of Aliphatic Aldehydes in Acid Media

Freeman, Fillmore,Lin, Doris K.,Moore, Gregory R.

, p. 56 - 59 (1982)

The kinetics and mechanism of the permanganate ion oxidation of 2,2-dimethylpropanal (pivalaldehyde, 4) and other aliphatic aldehydes over the pH range 2.80-6.86 have been investigated.The oxidation, which shows general-acid catalysis, is first order in and first order in ->.The mechanism of the Mn(VII) oxidation of aliphatic aldehydes is compared with that proposed for Cr(VI).

Oxygen-Atom Transfer from Iodosobenzene to Ketenes, α-Keto Carboxylic Acids, and Ketones

Moriarty, Robert M.,Gupta, Satish C.,Hu, Henry,Berenschot, Daniel M.,White, Kenneth B.

, p. 686 - 688 (1981)

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Yukawa et al.

, p. 2618,2619 (1967)

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Bryce-Smith

, p. 1079,1080, 1084 (1954)

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Towards the rehabilitation of the Mathews' 'dry' hydrolysis reaction using microwave technology

Chemat, Farid

, p. 5555 - 5557 (2002)

The Mathews' reaction is a one-pot preparation of carboxylic acids from their corresponding nitriles or amides by a 'dry' hydrolysis with phthalic acid or anhydride in the absence of water and solvent. Excellent isolated yields and selectivity (up to 99%) were attained within short reaction times (typically, 30 minutes) when the reaction was performed under microwave heating.

Relative activity of metal cathodes towards electroorganic coupling of CO2 with benzylic halides

Engelhardt, Helen,Klinkova, Anna,Medvedev, Jury J.,Medvedeva, Xenia V.

, (2021)

Electrochemical reduction of benzylic halides represents a convenient route to generating carbanions for their subsequent coupling with CO2 to obtain various carboxylic acids. Despite the industrial prospects of this synthetic process, it still lacks systematic studies of the efficient catalysts and reaction media design. In this work, we performed a detailed analysis of the catalytic activity of a series of different metal electrodes towards electroreduction of benzylic halides to corresponding radicals and carbanions using cyclic voltammetry. Specifically, we screened and summarized the performance of 12 bulk metal cathodes (Ag, Au, Cu, Pd, Pt, Ni, Ti, Zn, Fe, Al, Sn, and Pb) and 3 carbon-based materials (glassy carbon, carbon cloth, and carbon paper) towards electrocarboxylation of eight different benzylic halides and compare it to direct CO2 reduction in acetonitrile. Extensive experimental studies along with a detailed analysis of the results allowed us to map specific electrochemical properties of different metal electrodes, i.e., the potential zones related to the one- and two-electron reduction of organic halides as well as the potential windows where the electrochemical activation of CO2 does not occur. The reported systematic analysis should facilitate the development of nanostructured electrodes based on group 10 and 11 transition metals to further optimize the efficiency of electrocarboxylation of halides bearing specific substituents and make this technology competitive to current synthetic methods for the synthesis of carboxylic acids.

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Gilman,Pacevitz,Baine

, p. 1514,1519 (1940)

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Synthesis of Phenylacetic Acid via Carbonylation of Benzyl Chloride in the Presence of a Water-Soluble Complex, 2>, and Surfactants under Two-Phase Conditions

Okano, Tamon,Hayashi, Tetsuji,Kiji, Jitsuo

, p. 2339 - 2341 (1994)

The addition of surfactants such as n-C7H15SO3Na or n-C7H15COONa is effective in acceleration of the carboxylation of benzyl chloride using a water-soluble catalyst, 2>, in an aqueous NaOH-heptane solution.Phenylacetic acid is easily isolated from the aqueous layer in high yields.However, the addition of n-C7H15SO3Na has no effect on the carboxylation using hydrophobic catalysts, and , under the two phase conditions.

An 'easy-on, easy-off' protecting group for the enzymatic resolution of (±)-1-phenylethylamine in an aqueous medium

Guranda, Dorel T.,Khimiuk, Andrey I.,Van Langen, Luuk M.,Van Rantwijk, Fred,Sheldon, Roger A.,Svedas, Vytas K.

, p. 2901 - 2906 (2004)

A new approach has been developed for the biocatalytic resolution of (±)-1-phenylethylamine in 100% aqueous medium based on two integrated enzymatic steps: protection and deprotection of the reactive amine enantiomer catalyzed by the same enzyme-penicillin acylase from Alcaligenes faecalis. An 'easy-on, easy-off' protecting group has been introduced using (R)-phenylglycine amide as the acyl donor. (R)-Phenylglycyl-substituted (R)-1-phenylethylamine was poorly soluble and precipitated at enzymatic acylation in an alkaline medium (pH 10-11), driving the synthesis towards high yields. Conversely at pH 7.5, its solubility was continuously increasing, which rendered the subsequent deacylation by the same enzyme highly efficient. In contrast to the resolutions, which employ one biocatalytic step, the new approach made it possible to exploit two sequential enantioselective enzymatic reactions implementing a double enantioselectivity control. Effective enzymatic resolution of (±)-1-phenylethylamine in an aqueous medium was performed with (R)-phenylglycine amide as an acyl donor using the suggested approach.

The combi-CLEA approach: Enzymatic cascade synthesis of enantiomerically pure (S)-mandelic acid

Chmura, Andrzej,Rustler, Sven,Paravidino, Monica,Van Rantwijk, Fred,Stolz, Andreas,Sheldon, Roger A.

, p. 1225 - 1232 (2013)

Enantiomerically pure (S)-mandelic acid was synthesised from benzaldehyde by sequential hydrocyanation and hydrolysis in a bienzymatic cascade at starting concentrations up to 0.25 M. A cross-linked enzyme aggregate (CLEA) composed of the (S)-selective oxynitrilase from Manihot esculenta and the non-selective nitrilase from Pseudomonas fluorescens EBC 191 was employed as the biocatalyst. The nitrilase produces approx. equal amounts of (S)-mandelic acid and (S)-mandelic amide from (S)-mandelonitrile under standard conditions, but we surprisingly found that high (up to 0.5 M) concentrations of HCN induced a marked drift towards amide production. By including the amidase from Rhodococcus erythopolis in the CLEA we obtained (S)-mandelic acid as the sole product in 90% yield and >99% enantiomeric purity.

Cobalt carbonyl catalyzed carbonylation of benzal bromides by phase transfer catalysis

Shim, Sang Chul,Doh, Chil Hoon,Park, Woo Hyun,Kwon, Young Gil,Lee, Hyung Soo

, p. 419 - 421 (1990)

The reaction of benzal bromides with CO (1 atm) in a binary system (aq.KOH/C6H6) in the presence of a catalytic amount of Co2(CO)8 together with benzyltriethylammonium chloride as a phase transfer catalyst for 8 h at room temperature gives the corresponding carboxylic acids in good to excellent yields.

A recyclable, metal-free mechanochemical approach for the oxidation of alcohols to carboxylic acids

Carr, Preston,Denlinger, Kendra Leahy,Mack, James,Waddell, Daniel C.

, (2020)

The oxidation of primary alcohols under mechanochemical conditions in a Spex8000M Mixer/Mill was investigated. To facilitate ease of separation and recyclability, a polystyrene-bound version of a TEMPO catalyst was employed. When paired with Oxone in a stainless-steel vial with a stainless-steel ball, several primary alcohols were successfully oxidized to the corresponding carboxylic acids. The product was isolated using gravity filtration, which also allowed for the polystyrene-bound TEMPO catalyst to be recovered and reused in subsequent oxidation reactions. Furthermore, it was demonstrated that the size and steric hindrance of the primary alcohol does not hinder the rate of the reaction. Finally, the aldehyde was selectively obtained from a primary alcohol under ball milling conditions by using a combination of non-supported TEMPO with a copper vial and copper ball.

A versatile procedure for synthesis of organic acids by cobalt carbonyl catalyzed carbonylation of organic halides

Zhesko,Boyarskii,Nikitina

, p. 945 - 950 (2007)

A versatile procedure for synthesis of a broad range of fatty-aromatic and aromatic acids by carbonylation of the corresponding halides under very mild conditions in the presence of cobalt carbonyl as a catalyst was suggested. The main principles of a flexible process for production of practically significant acids and their derivatives were developed.

Efficient Assay for the Detection of Hydrogen Peroxide by Estimating Enzyme Promiscuous Activity in the Perhydrolysis Reaction

Wilk, Monika,Ostaszewski, Ryszard

, p. 1464 - 1469 (2021)

Hydrogen peroxide is an ideal oxidant in view of its availability, atom economy, or green aspects. Furthermore, it is produced by the cell mitochondria and plays a meaningful role in controlling physiological processes, but its unregulated production leads to the destruction of organs. Due to its diverse roles, a fast and selective method for hydrogen peroxide detection is the major limitation to preventing the negative effects caused by its excess. Therefore, we aimed to develop an efficient assay for the detection of H2O2. For this purpose, we combined the enzymatic method for the detection of hydrogen peroxide with the estimation of the promiscuity of various enzymes. We estimated the activity of an enzyme in the reaction of p-nitrophenyl esters with hydrogen peroxide resulting in the formation of peracid. To our knowledge, there is no example of a simple, multi-sensor demonstrating the promiscuous activity of an enzyme and detecting hydrogen peroxide in aqueous media.

Oxidation of aldehydes with Oxone in aqueous acetone

Webb, Kevin S.,Ruszkay, Stephen J.

, p. 401 - 410 (1998)

Several aldehydes have been convened to the corresponding acids in good to excellent yields. The oxidant was Oxone (potassium peroxymonosulfate), the reactions were performed in either 20% aqueous acetone, water, or aqueous acetonitrile, and buffered with sodium bicarbonate.

Site-selective immobilisation of functional enzymes on to polystyrene nanoparticles

Wong, Lu Shin,Okrasa, Krzysztof,MicKlefield, Jason

, p. 782 - 787 (2010)

The immobilisation of proteins on to nanoparticles has a number of applications ranging from biocatalysis through to cellular delivery of biopharmaceuticals. Here we describe a phosphopantetheinyl transferase (Sfp)-catalysed method for immobilising proteins bearing a small 12-mer "ybbR" tag on to nanoparticles functionalised with coenzyme A. The Sfp-catalysed immobilisation of proteins on to nanoparticles is a highly efficient, single step reaction that proceeds under mild conditions and results in a homogeneous population of proteins that are covalently and site-specifically attached to the surface of the nanoparticles. Several enzymes of interest for biocatalysis, including an arylmalonate decarboxylase (AMDase) and a glutamate racemase (GluR), were immobilised on to nanoparticles using this approach. These enzymes retained their activity and showed high operational stability upon immobilisation. The Royal Society of Chemistry 2010.

Trimethyl orthoformate as a highly selective mono-C-methylating agent for arylacetonitriles

Selva, Maurizio,Tundo, Pietro

, p. 9540 - 9544 (1998)

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Brown,Darwent

, p. 169 (1979)

Reductive carboxylation of alkyl halides with CO2by use of photoinduced SmI2/Sm reduction system

Nomoto, Akihiro,Kojo, Yusuke,Shiino, Go,Tomisaka, Yuri,Mitani, Ikuko,Tatsumi, Masahiko,Ogawa, Akiya

, p. 6580 - 6583 (2010)

Upon visible-light irradiation, reductive carboxylation of alkyl halides takes place by using a Sml2/Sm mixed system under atmospheric CO 2 to afford the corresponding carboxylic acids in good to excellent yields.

A simple and efficient protocol for the deprenylation of ethers and esters catalysed by zirconium(IV) chloride-sodium iodide

Sharma, Gangavaram V. M.,Reddy, Ch. Govardhan,Krishna, Palakodety Radha

, p. 1728 - 1730 (2003)

An efficient protocol for the deprotection of prenyl ethers and esters is developed using 20 mol% ZrCl4-NaI (1:1) in CH3CN as a reagent system. A variety of substrates as well as functional groups well tolerate the present reaction conditions.

SELECTIVE HYDROLYSIS OF NITRILES UNDER MILD CONDITIONS BY AN ENZYME

Cohen, Mark A.,Sawden, Janette,Turner, Nicholas J.

, p. 7223 - 7226 (1990)

A wide range of aromatic/aliphatic nitriles and dinitriles have been selcetively hydrolysed using a commercially available enzyme preparation from a Rhodococcuc sp.

Isolation of 2-Alkyl-4-quinolones with Unusual Side Chains from a Chinese Pseudomonas aeruginosa Isolate

Li, Jianye,Sun, Weiwei,Saalim, Muhammad,Wei, Guixiang,Zaleta-Pinet, Diana A.,Clark, Benjamin R.

, p. 2294 - 2298 (2020)

Chemical investigation of a Pseudomonas aeruginosa strain isolated from Hebei, China, led to the isolation of a suite of quinolones, quinolone-N-oxides, and phenazines, the structures of which were elucidated by detailed spectroscopic analysis. Most notable among the secondary metabolites isolated was an unprecedented 4-quinolone containing an S-methyl group in the side chain and a new derivative including a phenyl ring in the side chain, which expand significantly the variety of structural motifs found in the quinolones and raise interesting questions about their biosynthesis.

Ultrathin and Vacancy-Rich CoAl-Layered Double Hydroxide/Graphite Oxide Catalysts: Promotional Effect of Cobalt Vacancies and Oxygen Vacancies in Alcohol Oxidation

Wang, Qian,Chen, Lifang,Guan, Shaoliang,Zhang, Xin,Wang, Bin,Cao, Xingzhong,Yu, Zhi,He, Yufei,Evans, David G.,Feng, Junting,Li, Dianqing

, p. 3104 - 3115 (2018)

Co-containing layered double hydroxides (LDHs) are potential non-noble-metal catalysts for the aerobic oxidation of alcohols. However, the intrinsic activity of bulk LDHs is relatively low. In this work, we fabricated ultrathin and vacancy-rich nanosheets by exfoliating bulk CoAl-LDHs, which were then assembled with graphite oxide (GO) to afford a hybrid CoAl-ELDH/GO catalyst. TEM, AFM, and positron annihilation spectrometry indicate that the thickness of the exfoliated LDH platelets is about 3 nm, with a large number of vacancies in the host layers. Fourier transformed XAFS functions show that the Co-O and Co····Co coordination numbers (5.5 and 2.8, respectively) in the hybrid CoAl-ELDH/GO material are significantly lower than the corresponding values in bulk CoAl-LDHs (6.0 and 3.8, respectively). Furthermore, in addition to the oxygen vacancies (VO) and cobalt vacancies (VCo), CoAl-ELDH/GO also contains negatively charged VCo-Co-OHδ- sites and exposed lattice oxygen sites. CoAl-ELDH/GO shows excellent performance as a catalyst for the aerobic oxidation of benzyl alcohol, with a TOF of 1.14 h-1; this is nearly five times that of the unexfoliated bulk CoAl-LDHs (0.23 h-1) precursor. O2-TPD and DRIFT spectroscopy declare that the oxygen storage capacity and mobility are facilitated by the oxygen vacancies and surface lattice oxygen sites. Meanwhile, DFT calculations of adsorption energy show that benzyl alcohol is strongly adsorbed on the oxygen vacancies and negatively charged VCo-Co-OHδ- sites. A kinetic isotope effect study further illustrates that the vacancy-rich CoAl-ELDH/GO catalyst accelerates the cleavage of the O-H bond in benzyl alcohol. Finally, we show that the hybrid CoAl-ELDH/GO material exhibits excellent catalytic activity and selectivity in the oxidation of a range of other benzylic and unsaturated alcohols.

Alper,Des Abbayes

, p. C11,C12-C14 (1977)

Fluorinated analogues of tert-butyl alcohol as novel protecting groups for use in fluorous synthesis

Pardo, Juan,Cobas, Agustin,Guitian, Enrique,Castedo, Luis

, p. 3711 - 3714 (2001)

Figure presented A series of fluorous derivatives of tert-butyl alcohol were prepared and evaluated as reagents for the protection of carboxylic acids for use in fluorous synthesis. Alcohol 3b can be employed efficiently to protect and immobilize medium-size nonpolar carboxylic acids in a fluorous phase.

Cassar,Foa

, p. C15 (1977)

SILAFUNCTIONAL COMPOUNDS IN ORGANIC SYMTHESIS. 21. HYDROGEN PEROXIDE OXIDATION OF ALKENYL(ALKOXY)SILANES

Tamao, Kohei,Kumada, Makoto,Maeda, Kimio

, p. 321 - 324 (1984)

The carbon-silicon bond in alkenyl(alkoxy)silanes is readily cleaved by hydrogen peroxyde to form the corresponding aldehydes, carboxylic acids or ketones, depending upon the nature of the alkenyl group and the reaction conditions.

Design and evolution of an enzyme with a non-canonical organocatalytic mechanism

Burke, Ashleigh J.,Lovelock, Sarah L.,Frese, Amina,Crawshaw, Rebecca,Ortmayer, Mary,Dunstan, Mark,Levy, Colin,Green, Anthony P.

, p. 219 - 223 (2019)

The combination of computational design and laboratory evolution is a powerful and potentially versatile strategy for the development of enzymes with new functions1–4. However, the limited functionality presented by the genetic code restricts the range of catalytic mechanisms that are accessible in designed active sites. Inspired by mechanistic strategies from small-molecule organocatalysis5, here we report the generation of a hydrolytic enzyme that uses Nδ-methylhistidine as a non-canonical catalytic nucleophile. Histidine methylation is essential for catalytic function because it prevents the formation of unreactive acyl-enzyme intermediates, which has been a long-standing challenge when using canonical nucleophiles in enzyme design6–10. Enzyme performance was optimized using directed evolution protocols adapted to an expanded genetic code, affording a biocatalyst capable of accelerating ester hydrolysis with greater than 9,000-fold increased efficiency over free Nδ-methylhistidine in solution. Crystallographic snapshots along the evolutionary trajectory highlight the catalytic devices that are responsible for this increase in efficiency. Nδ-methylhistidine can be considered to be a genetically encodable surrogate of the widely employed nucleophilic catalyst dimethylaminopyridine11, and its use will create opportunities to design and engineer enzymes for a wealth of valuable chemical transformations.

Cathode made of compacted silver nanoparticles for electrocatalytic carboxylation of 1-phenethyl bromide with CO2

Yang, Hengpan,Wu, Laxia,Wang, Huan,Lu, Jiaxing

, p. 994 - 998 (2016)

Silver nanoparticles prepared by the direct reduction of AgNO3 in aqueous solution were compacted into coins and used as the cathode for the electrocatalytic carboxylation of 1-phenethyl bromide with CO2. The influences of the working electrode, charge, current density and temperature were investigated. Under optimized conditions, 98% yield of 2-phenylpropionic acid was obtained. The reaction was performed under very mild conditions and no added catalyst was required in the electrolyte. Yields that varied from moderate to excellent were also achieved with other benzyl bromides. This electrode has good stability and reusability, and the yield and selectivity of 2-phenylpropionic acid could be maintained during reuse for 10 times.

Microwave-assisted oxidation of alcohols by hydrogen peroxide catalysed by tetrabutylammonium decatungstate

Galica, Mateusz,Kasprzyk, Wiktor,Bednarz, Szczepan,Bogdal, Dariusz

, p. 1240 - 1244 (2013)

This work deals with catalytic activity of tetrabutylammonium decatungstate(VI) in the oxidation of selected alcohols with hydrogen peroxide as an oxidant using 1,2-dichloroethane/water or acetonitrile/water as a solvent system. Different forms of heating were compared. The highest conversions of substrates were achieved in the two phase system acetonitrile/water using microwave irradiation combined with elevated pressure. Finally, optimum parameters for these reactions in a microwave pressurised reactor were established and discussed.

Purification, characterization and in-silico analysis of nitrilase from Gordonia terrae

Kumar, Vijay,Seth, Amit,Kumari, Vijaya,Kumar, Virender,Bhalla, Tek C.

, p. 52 - 62 (2015)

An inducible and aromatic nitrilase from Gordonia terrae was purified with a yield of 19%. The enzyme had turnover number of 63 s-1 × 10-3, Km1.4 mM and Vmax95 Umg-1 protein for benzonitrile. The nitrilase of G. terrae was active at basic pH (7-10), moderate temperature (20-45 °C) and has a half-life of 4 h at 35 °C. MALDI analysis and amino acid sequence deduced from cloned nucleotide fragment showed 97% homology with putative amidohydrolase of Gordonia sputi NBRC 100414 and G. namibiensis. The enzyme showed regioselectivity towards hydroxybenzonitriles, as different position of hydroxyl group i.e. meta-, para- and orthosubstitutions on benzonitrile effect enzyme activity. The in-silico interactions of these substrates with the predicted 3D model of this enzyme also showed differential interaction between hydroxyl group of substrates and the polar amino acids surrounding enzyme's active site. This leads to different proximity and orientation of substrates vis-a-vis their interaction with catalytic residues.

Resolution of (RS)-phenylglycinonitrile by penicillin acylase-catalyzed acylation in aqueous medium

Chilov, Ghermes G.,Moody, Harold M.,Boesten, Wilhelmus H. J.,Svedas, Vytas K.

, p. 2613 - 2617 (2003)

A new strategy for the biocatalytic resolution of (R,S)-phenylglycinonitrile, a crucial intermediate in the antibiotic industry, has been developed. While former techniques exploit nitrilases or combinations of nitrile hydratases and amidases, manipulating with nitrile functionality, the current approach is based on a highly efficient and enantioselective acylation of the α-amino group with phenylacetic acid catalyzed by a well known enzyme, penicillin acylase from E. coli, in slightly acidic aqueous medium. It is shown that since the condensation product is poorly soluble, removal of (S)-phenylglycinonitrile from the reaction sphere is almost complete and irreversible, favoring kinetics of the process and making high conversion possible. The proposed approach is characterized by high space-time yield and extends the scope of enzymatic synthesis in aqueous medium.

SIMPLE METHOD FOR THE CONVERSION OF TERMINAL OLEFINS TO CARBOXYLIC ACIDS WITH THE SAME CARBON SKELETON

Hao, Nguen Kong,Mavrov, M. V.,Serebryakov, E. P.

, p. 235 (1986)

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Nickel-Catalyzed Carboxylation of Benzylic C-N Bonds with CO2

Moragas, Toni,Gaydou, Morgane,Martin, Ruben

, p. 5053 - 5057 (2016)

A user-friendly Ni-catalyzed reductive carboxylation of benzylic C-N bonds with CO2 is described. This procedure outperforms state-of-the-art techniques for the carboxylation of benzyl electrophiles by avoiding commonly observed parasitic pathways, such as homodimerization or β-hydride elimination, thus leading to new knowledge in cross-electrophile reactions.

On the Conformation of the Substrate Binding to the Active Site during the Course of Enzymatic Decarboxylation

Kawasaki, Takayasu,Horimai, Emiko,Ohta, Hiromichi

, p. 3591 - 3594 (1996)

The activation parameters of the enzymatic decarboxylation of malonic acid derivatives catalyzed by arylmalonate decarboxylase (AMDase) were obtained by means of kinetics. In order to understand the conformation of the substrate at the transition state, the activation entropy (ΔS?) for indane-1,1-dicarboxylic acid, a representative molecule that is conformationally restricted, was compared with those of phenylmalonic acid and ortho-chlorophenylmalonic acid, of which the aromatic ring can freely rotate. The obtained value for the former molecule was about 10 cal mol-1 K-1 smaller than those of the latter compounds, clearly indicating that a conformationally restricted substrate, such as the indane derivative, is entropically advantageous for enzymatic decarboxylation. These kinetic studies evidently disclose that the conformation of the substrate at the transition state in the course of AMDase-catalyzed decarboxylation should be synperiplanar with regard to ortho- and α-substituents.

A simple and highly practical oxidation of primary alcohols to acids mediated by 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)

Zanka, Atsuhiko

, p. 888 - 889 (2003)

Primary alcohols were quantitatively oxidized in one-pot to acids via 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) mediated oxidation. The reported method is simple and suitable for large scale synthesis.

Direct Photolysis of Phenacyl Protecting Groups Studied by Laser Flash Photolysis: An Excited State Hydrogen Atom Abstraction Pathway Leads to Formation of Carboxylic Acids and Acetophenone

Banerjee, Anamitro,Falvey, Daniel E.

, p. 2965 - 2966 (1998)

-

-

Johnson,Jacobs,Schwartz

, p. 1885,1888 (1938)

-

Ruthenium molecular complexes immobilized on graphene as active catalysts for the synthesis of carboxylic acids from alcohol dehydrogenation

Ventura-Espinosa, David,Vicent, Cristian,Baya, Miguel,Mata, Jose A.

, p. 8024 - 8035 (2016)

Ruthenium complexes containing N-heterocyclic carbene ligands functionalized with different polyaromatic groups (pentafluorophenyl, anthracene, and pyrene) are immobilized onto the surface of reduced graphene oxide. The hybrid materials composed of organometallic complexes and graphene are obtained in a single-step process. The hybrid materials are efficient catalysts for the synthesis of carboxylic acids from the dehydrogenation of alcohols in aqueous media. The catalytic materials can be recycled up to ten times without significant loss of activity. The catalytic activity of the pyrene derivative, Pyr-Ru (3) is enhanced when the ruthenium complex is anchored onto the surface of graphene. The carbonaceous material limits the degradation of the ruthenium complex resulting in increased activity and requiring lower catalyst loading. The catalytic process of the pyrene hybrid material is heterogeneous in nature due to the strong interaction between the pyrene and graphene. The catalytic process of the anthracene and pentafluorophenyl hybrid materials is governed by the so-called 'boomerang effect'. The ruthenium molecular complex is released from and returned to the graphene surface during the catalytic reaction. Mechanistic insight has been obtained experimentally and theoretically. The energy profile suggests that the ratedetermining step is the nucleophilic attack of water on a coordinated aldehyde complex to form a gem-diolate complex.

Comparison of Spectroscopic and Electrochemical Studies of Disproportionation Equilibria of 1,3,5-Triphenylverdazyl Radical in DMF Containing Carboxylic Acids

Jaworski, Jan S.,Krawczyk, Irena

, p. 43 - 50 (1992)

Stoichiometry and equilibrium constants for the disproportionation of the title radicals in N,N-dimethylformamide containing salicilic, chloroacetic, and phenylacetic acids were determined on the basis of absorption spectra.On the other hand, only apparent equilibrium constants depending on concentrations of an acid and a radical could be obtained from electrochemical measurements at a mercury electrode.Significant differences in reaction stoichiometry and in order of magnitudes of disproportionation constants found under spectroscopic and electrochemical conditionswere discussed in terms of an influence of the electric field in the double layer on the distribution of different associates formed by verdazyl species with acids.Keywords: Disproportionation equilibrium; Effect of the electrode field.

-

Miescher,Billeter

, p. 601,609 (1939)

-

Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process

Fu, Qiang,Liang, Fu-Shun,Lou, Da-Wei,Pan, Gao-Feng,Wang, Rui,Wu, Min,Xie, Kai-Jun

supporting information, p. 2020 - 2024 (2022/03/31)

A visible-light-promoted atomic substitution reaction for transforming thiocacids into carboxylic acids with dimethyl sulfoxide (DMSO) as the oxygen source has been developed, affording various alkyl and aryl carboxylic acids in over 90% yields. The atomic substitution process proceeds smoothly through the photochemical reactivity of the formed hydrogen-bonding adduct between thioacids and DMSO. A DMSO-involved proton-coupled electron transfer (PCET) and the simultaneous generation of thiyl and hydroxyl radicals are proposed to be key steps for realizing the transformation.

Direct Aerobic α-Hydroxylation of Arylacetates for the Synthesis of Mandelates

Xu, Changming,Li, Xiangfan,Bai, Lei

, p. 4298 - 4304 (2022/03/16)

Aerobic α-hydroxylation of α-methylene esters has proven challenging due to overoxidation and hydrolysis of the materials. In this article, KOtBu-promoted TBAB-catalyzed α-hydroxylation of α-methylene aryl esters using O2as the oxyge

Mechanochemical Grignard Reactions with Gaseous CO2 and Sodium Methyl Carbonate**

Pfennig, Victoria S.,Villella, Romina C.,Nikodemus, Julia,Bolm, Carsten

supporting information, (2022/01/22)

A one-pot, three-step protocol for the preparation of Grignard reagents from organobromides in a ball mill and their subsequent reactions with gaseous carbon dioxide (CO2) or sodium methyl carbonate providing aryl and alkyl carboxylic acids in up to 82 % yield is reported. Noteworthy are the short reaction times and the significantly reduced solvent amounts [2.0 equiv. for liquid assisted grinding (LAG) conditions]. Unexpectedly, aryl bromides with methoxy substituents lead to symmetric ketones as major products.

PYRROLIDINE-PYRAZOLES AS PYRUVATE KINASE ACTIVATORS

-

Paragraph 173-175, (2021/10/11)

The subject matter described herein is directed to pyruvate kinase activating compounds of Formula I and pharmaceutical salts thereof, methods of preparing the compounds, pharmaceutical compositions comprising the compounds and methods of administering the compounds for the treatment of diseases associated with PKR and/or PKM2, such as pyruvate kinase deficiency, sickle cell disease, and beta-thalassemia.

Polyalkynyl-containing alpha, beta-diamino acid ester derivative compound as well as preparation and application of thereof

-

Paragraph 0057-0058, (2021/04/28)

The invention discloses a polyalkynyl-containing alpha, beta-diamino acid ester derivative compound or a pharmaceutically acceptable salt, and an application of the compound or a pharmaceutical composition containing the compound in treating various malignant tumor related diseases such as osteosarcoma, pancreatic cancer, head and neck tumors and the like. The invention further relates to a preparation method of the polyalkynyl-containing alpha, beta-diamino acid ester derivative compound or the pharmaceutically acceptable salt.

Process route upstream and downstream products

Process route

t-butyl phenylperacetate
3377-89-7

t-butyl phenylperacetate

phenylacetic acid
103-82-2

phenylacetic acid

benzyl bromide
100-39-0

benzyl bromide

acetone
67-64-1

acetone

benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

Conditions
Conditions Yield
With toluene-p-sulfonyl bromide; In benzene; at 70 ℃; for 40h; Further byproducts given;
139.7 mg
51.6 mg
153.0 mg
20.5 mg
t-butyl phenylperacetate
3377-89-7

t-butyl phenylperacetate

phenylacetic acid
103-82-2

phenylacetic acid

benzyl bromide
100-39-0

benzyl bromide

benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

<i>tert</i>-butyl alcohol
75-65-0

tert-butyl alcohol

Conditions
Conditions Yield
With toluene-p-sulfonyl bromide; In benzene; at 70 ℃; for 40h; Further byproducts given;
51.6 mg
153.0 mg
4.0 mg
139.7 mg
N-Methyl-N-(4-nitro-phenyl)-2-phenyl-acetamide

N-Methyl-N-(4-nitro-phenyl)-2-phenyl-acetamide

phenylacetic acid
103-82-2

phenylacetic acid

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
Conditions Yield
With barium dihydroxide; cetyltrimethylammonim bromide; In water; at 30 ℃; Rate constant; Mechanism; dependence of rate constant on concentration of cetyltrimethylammonium bromide;
methanol
67-56-1

methanol

2-bromo-1-(1-naphthyl)ethyl phenylacetate
189164-96-3

2-bromo-1-(1-naphthyl)ethyl phenylacetate

phenylacetic acid
103-82-2

phenylacetic acid

1-(1-napthyl)ethyl methyl ether
83815-96-7

1-(1-napthyl)ethyl methyl ether

benzyl bromide
100-39-0

benzyl bromide

2-bromo-1-methoxy-1-(1-naphthyl)ethane

2-bromo-1-methoxy-1-(1-naphthyl)ethane

1,1-dimethoxy-2-(1-naphthyl)ethane

1,1-dimethoxy-2-(1-naphthyl)ethane

benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

Conditions
Conditions Yield
Mechanism; Irradiation; other 1-naphthylmethyl phenylacetates;
phenylacetonitrile
140-29-4

phenylacetonitrile

trimethyl orthoformate
149-73-5

trimethyl orthoformate

phenylacetic acid
103-82-2

phenylacetic acid

2-methyl-2-phenylpropionitrile
1195-98-8

2-methyl-2-phenylpropionitrile

1-phenylethyl cyanide
1823-91-2

1-phenylethyl cyanide

Conditions
Conditions Yield
With potassium tert-butylate; at 190 ℃; for 1h; Product distribution; other temperature, reaction time, effect of cosolvents; various ratios of base and substrate, various amounts of MeOH as cosolvent;
28 % Chromat.
11 % Chromat.
25 % Chromat.
ethyl 3-oxo-4-phenylbutyrate
718-08-1

ethyl 3-oxo-4-phenylbutyrate

sulfuric acid
7664-93-9

sulfuric acid

phenylacetic acid
103-82-2

phenylacetic acid

1,3-dihydroxynaphthalene
132-86-5

1,3-dihydroxynaphthalene

1-phenyl-acetone
103-79-7,136675-26-8

1-phenyl-acetone

Conditions
Conditions Yield
2-benzyl-3-(4-methoxy-phenyl)-acrylic acid
126356-03-4

2-benzyl-3-(4-methoxy-phenyl)-acrylic acid

phenylacetic acid
103-82-2

phenylacetic acid

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
tetrachloromethane
56-23-5

tetrachloromethane

3-hydroxy-3-(4-methoxy-phenyl)-2-phenyl-butyric acid
101595-39-5

3-hydroxy-3-(4-methoxy-phenyl)-2-phenyl-butyric acid

phenylacetic acid
103-82-2

phenylacetic acid

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
Conditions Yield
at 55 ℃; Rate constant; sowie bei 65grad und 75grad;
bis-(2-phenylacetylamino-ethyl)-carbamic acid 4-nitro-phenyl ester
757967-03-6

bis-(2-phenylacetylamino-ethyl)-carbamic acid 4-nitro-phenyl ester

phenylacetic acid
103-82-2

phenylacetic acid

2-aminoethylimidazolidone
6281-42-1

2-aminoethylimidazolidone

(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

Conditions
Conditions Yield
With water; penicillin-G-amidase; In Chremephor EL; dimethyl sulfoxide; at 37 ℃; pH=7.4; Kinetics; Enzymatic reaction; Aqueous phosphate buffer;
N-(4-nitrophenyl)-2-phenylacetamide
13140-77-7

N-(4-nitrophenyl)-2-phenylacetamide

phenylacetic acid
103-82-2

phenylacetic acid

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

Conditions
Conditions Yield
With Escherichia coli penicillin acylase; potassium chloride; water; at 24.84 ℃; Equilibrium constant; Enzymatic reaction;

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