62977-82-6

Basic information

• Product Name: Benzeneacetic acid, a-oxo-, phenylmethyl ester
• Synonyms: oxo-phenyl-acetic acid benzyl ester;benzyl-2-oxo-2-phenylacetate;benzyl 2-oxo-2-phenylacetate;benzyl oxo(phenyl)acetate;benzyl-α-oxophenyl acetate;phenylglyoxylic acid benzyl ester
• CAS NO: 62977-82-6
• Molecular Formula: C15H12O3
• Molecular Weight: 240.258
• Mol File: 62977-82-6.mol
• Article Data: 49

Chemical Properties

• Boiling Point: 372.7±21.0 °C(Predicted)
• Density: 1.191±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzeneacetic acid, a-oxo-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, a-oxo-, phenylmethyl ester(62977-82-6)
• EPA Substance Registry System: Benzeneacetic acid, a-oxo-, phenylmethyl ester(62977-82-6)

Safety Data

• Hazardous Substances Data: 62977-82-6(Hazardous Substances Data)

Upstream product

• 25726-04-9 phenylglyoxylyl chloride 
• 85166-50-3 N-Nitroso-N-benzylhydroxylamine Sodium Salt 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 100-51-6 benzyl alcohol 
• 5032-98-4 2-triphenylphosphorylidene-3-oxo-3-phenylpropionitrile 
• 29601-98-7 N-benzylhydroxylamine hydrochloride 
• 28571-11-1 N-benzyl-N-nitroso-hydroxylamine 
• 62173-99-3 benzyl 2-hydroxy-2-phenylacetate 
• 78823-32-2 benzoic formic anhydride 
• 63468-90-6 phenylglyoxylic acid potassium salt 
• 100-44-7 benzyl chloride 
• 611-73-4 Benzoylformic acid 
• 501-53-1 benzyl chloroformate 
• 20067-23-6 3-benzyl-4-phenyl-1,2,3-oxadiazol-3-ium-5-olate 

Downstream Products

• 1042740-65-7 (S)-benzyl 2-hydroxy-2-(4-methylphenyl)-phenylacetate 
• 1042740-62-4 (R)-benzyl 2-hydroxy-2-(4-methylphenyl)-phenylacetate 
• 1042740-67-9 (S)-benzyl 2-hydroxy-2-(4-methoxyphenyl)-2-phenylacetate 
• 1042740-63-5 (R)-benzyl 2-hydroxy-2-(4-methoxyphenyl)-2-phenylacetate 
• 62173-99-3 benzyl 2-hydroxy-2-phenylacetate 
• 97415-09-3 (R)-benzyl 2-hydroxy-2-phenyl-acetate 
• 1344689-92-4 benzyl 2-hydroxy-4-(4-methoxyphenyl)-2-phenylbut-3-ynoate 
• 1041482-57-8 benzyl 2-((4-methoxyphenyl)imino)-2-phenylacetate 
• 1453490-61-3 C₂₆H₂₅NO₅S 
• 1449336-26-8 C₂₂H₁₉NO₄S 
• 1201153-94-7 benzyl 2-hydroxy-2-phenylpent-4-enoate 
• 1416912-97-4 benzyl (R)-2-hydroxy-3-(3-oxocyclohex-1-en-1-yl)-2-phenylpropanoate 
• 1408233-68-0 C₂₁H₂₇NO₃Si 
• 1408233-67-9 C₂₂H₁₉NO₅S 

Relevant articles and documents

Unraveling two pathways for NHPI-mediated electrocatalytic oxidation reaction

Two pathways for N-hydroxyphthalimide (NHPI)-mediated electrocatalytic oxidation using phenylacetate derivatives as template substrates were first reported for benzylic C[sbnd]H oxidation to oxygenated and non-oxygenated products. DFT calculation indicates that the hydrogen-atom transfer (HAT) process between phthalimido-N-oxyl (PINO) and substrate is a rate-determined step. Aromatic α-keto esters and 2-((1,3-dioxoisoindolin-2-yl)oxy)-2-aryl acetate obtained by cross-coupling between benzylic radical and PINO can be selectively synthesized through controlling the concentration of PINO radical. This method provides a deep understanding for selective weak C[sbnd]H oxidation using NHPI as redox mediator.

Copper on charcoal: Cu0nanoparticle catalysed aerobic oxidation of α-diazo esters

By using a charcoal supported nano Cu0catalyst (Cu/C), a highly efficient oxidation of α-diazo esters to α-ketoesters with molecular oxygen as the sole oxidant has been developed. In the presence of the Cu/C catalyst, 2-aryl-α-diazo esters with both electron-donating and electron-withdrawing groups can be oxidized to the corresponding α-ketoesters efficiently. Furthermore, this Cu/C catalyst can catalyse the reaction of aryl α-diazo ester with water to form aryl ketoester, 2-aryl-2-hydroxyl acetate ester and 2-aryl acetate ester. In this case, water is split by α-diazo ester, and the diazo group is displaced by the oxygen or hydrogen atom in water. Mechanistic investigation showed that the reaction of α-diazo ester with oxygen proceeds through a radical pathway. In the presence of 2,2,6,6-tetramethyl piperidine nitrogen oxide, the reaction of α-diazo ester with oxygen is dramatically inhibited. Furthermore, the reaction of α-diazo ester with water is investigated by an isotopic tracer method, and GCMS detection showed that a disproportionation reaction occurred between α-diazo ester and water.

Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters

A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.