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1603-79-8

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1603-79-8 Usage

Chemical Properties

clear colorless to greenish liquid

Uses

Ethyl Benzoylformate is a general chemical reagent used in the preparation of diaminoethanediyl bismethylpyridinium salts for designing recyclable organocatalysts.

Application

Ethyl benzoylformate has been used in preparation of 1,5-dihydro-5-deazaflavin derivatives possessing a chiral substituent at N(3) position.

Definition

ChEBI: Ethyl benzoylformate is the ethyl ester of phenylglyoxylic acid. Metabolite observed in cancer metabolism. It has a role as a human metabolite. It derives from a phenylglyoxylic acid.

Synthesis Reference(s)

Journal of the American Chemical Society, 82, p. 918, 1960The Journal of Organic Chemistry, 50, p. 3573, 1985 DOI: 10.1021/jo00219a025Tetrahedron Letters, 23, p. 3661, 1982 DOI: 10.1016/S0040-4039(00)88651-7

General Description

Enantioselective hydrogenation of ethyl benzoylformate on Pt/Al2O3 modified with dihydrocinchonidine has been studied.

Check Digit Verification of cas no

The CAS Registry Mumber 1603-79-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,6,0 and 3 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1603-79:
(6*1)+(5*6)+(4*0)+(3*3)+(2*7)+(1*9)=68
68 % 10 = 8
So 1603-79-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H10O3/c1-2-13-10(12)9(11)8-6-4-3-5-7-8/h3-7H,2H2,1H3

1603-79-8 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (B25292)  Ethyl phenylglyoxylate, 98%   

  • 1603-79-8

  • 5g

  • 347.0CNY

  • Detail
  • Alfa Aesar

  • (B25292)  Ethyl phenylglyoxylate, 98%   

  • 1603-79-8

  • 25g

  • 1026.0CNY

  • Detail
  • Alfa Aesar

  • (B25292)  Ethyl phenylglyoxylate, 98%   

  • 1603-79-8

  • 100g

  • 3286.0CNY

  • Detail

1603-79-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl phenylglyoxylate

1.2 Other means of identification

Product number -
Other names ethyl 2-oxo-2-phenylacetate

1.3 Recommended use of the chemical and restrictions on use

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

1.4 Supplier's details

1.5 Emergency phone number

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

More Details:1603-79-8 SDS

1603-79-8Related news

Reduction of Ethyl benzoylformate (cas 1603-79-8) mediated by Saccharomyces cerevisiae entrapped in alginate fibers with double gel layers in a continuously operated reactor07/17/2019

The first example of immobilized baker's yeast in alginate fibers with double-layer mediated reduction of ketones is described. The asymmetric reduction of ethyl benzoylformate (EBF) to ethyl (R)-mandelate ((R)-EM) in a continuous process was carried out in a packed bed reactor with Sacchar...detailed

1603-79-8Relevant articles and documents

Addition of grignard reagents to 1-(N-(Alkoxyoxalyl)-JV-methylamino)-3-methylimidazolium Salts: A general method for α-keto ester synthesis

De Las Heras, Maria A.,Vaquero, Juan J.,Garcia-Navio, Jose L.,Alvarez-Builla, Julio

, p. 9009 - 9011 (1996)

-

-

Wright

, p. 4883 (1955)

-

A trispyrazolylborato iron malonato complex as a functional model for the acetylacetone dioxygenase

Siewert, Inke,Limberg, Christian

, p. 7953 - 7956 (2008)

(Chemical Equation Presented) Position available: A pentacoordinate iron(II) complex that binds and activates dioxygen shows dioxygenase activity and cleaves diethyl phenylmalonate, in analogy to acetylacetone dioxygenase (see scheme). The mechanism for the model compound allows interesting hypotheses to be made about the enzyme function.

Copper-catalysed Oxidation of Hydroxy Compounds by tert-Butyl Hydroperoxide Under Phase-transfer Conditions

Feldberg, Liron,Sasson, Yoel

, p. 1807 - 1808 (1994)

In the presence of quaternary ammonium phase-transfer agents copper salts catalyse the selective oxidative dehydrogenation of alcohols and hydroxy acids by tert-butyl hydroperoxide in aqueous-organic two-phase systems.

VO(OEt)Cl2-induced oxidative deamination

Hirao, Toshikazu,Ohshiro, Yoshiki

, p. 3917 - 3918 (1990)

VO(OEt)Cl2 oxidized 2-phenylglycine derivatives via oxidative deamination and/or decarboxylation giving ethyl benzoate and ethyl phenylglyoxylate.

Metal-free oxidative esterification of acetophenones with alcohols: A facile one-pot approach to α-ketoesters

Guo, Shiyu,Dai, Zhongxue,Yang, Zhao,Zhu, Ning,Wan, Li,Li, Xin,Liu, Chengkou,Fang, Zheng,Guo, Kai

, p. 98422 - 98426 (2016)

A novel and efficient oxidative esterification method for the synthesis of α-ketoesters has been developed under mild and environmentally benign conditions, which is a facile one-pot approach to α-ketoesters from commercially available acetophenones with alcohols, especially under metal-free conditions, with broad substrate scope. A possible mechanism is proposed on the basis of a series of control experiments and DMSO18 isotopic labelling experiments.

A remarkable effect of quaternary ammonium bromide for the N- hydroxyphthalimide-catalyzed aerobic oxidation of hydrocarbons

Matsunaka, Katsuhisa,Iwahama, Takahiro,Sakaguchi, Satoshi,Ishii, Yasutaka

, p. 2165 - 2168 (1999)

A methodology for the aerobic oxidation of organic substrates in the absence of any metal catalyst has been established using combined catalytic system consisting of N-hydroxyphthalimide and quaternary ammonium bromide. Thus, various hydrocarbons were successfully oxidized under dioxygen atmosphere to the corresponding oxygenated compounds in good selectivities.

FACTORS AFFECTING DYE SENSITISED PHOTO-OXIDATION REACTIONS; THE EFFECT OF OXYGEN CONCENTRATION AND ITS USE TO PROBE THE MECHANISM OF DECARBOXYLATION OF α-OXO-CARBOXYLIC ACIDS AND ESTERS

Davidson, R. Stephen,Goodwin, Dean,Pratt, Julie E.

, p. 2373 - 2380 (1983)

The dye sensitised photo-oxidation of α-oxo-carboxylic acids and esters leads to the production of carbon dioxide.The yield of carbon dioxide is dependent upon the oxygen concentration.This, together with the fact that carbon dioxide evolution can be observed in the absence of oxygen, is in accord with the view that the decarboxylation reactions involve an initial dye-substrate interaction rather than a singlet oxygen mediated reaction.

Unraveling two pathways for NHPI-mediated electrocatalytic oxidation reaction

Xu, Leitao,Yi, Yangjie,Hu, Sideng,Ye, Jiao,Hu, Aixi

, (2021/11/30)

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.

Asymmetric Aldol Reaction of Alkenyl Esters with α-Keto Esters Catalyzed by Chiral Tin Alkoxides

Takagi, Kotaro,Uchiyama, Chika,Yanagisawa, Akira

supporting information, p. 2085 - 2089 (2021/12/01)

A catalytic enantioselective aldol reaction of alkenyl esters with α-keto esters was achieved by using an (R)-BINOL-derived chiral tin dibromide possessing 4-t-butylphenyl groups at the 3- and 3′-positions as a chiral precatalyst in the presence of sodium methoxide and methanol. Optically active aldol products possessing a chiral tertiary carbon were diastereoselectively obtained with up to 92% ee and moderate to high yields, not only from cyclic alkenyl esters, but also from acyclic ones under the influence of the chiral tin methoxide generated in situ.

Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes

Roy, Sourav,Kumar, Gourav,Chatterjee, Indranil

, p. 6709 - 6713 (2021/09/08)

A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.

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