Ethyl benzoylformate

Base Information

• Chemical Name: Ethyl benzoylformate
• CAS No.: 1603-79-8
• Molecular Formula: C10H10O3
• Molecular Weight: 178.188
• Hs Code.: 29183000
• European Community (EC) Number: 216-504-0
• NSC Number: 6766
• UNII: AMN28N4D74
• DSSTox Substance ID: DTXSID1061815
• Nikkaji Number: J102.635F
• Wikidata: Q27157626
• Mol file: 1603-79-8.mol

Synonyms:ethyl phenylglyoxylate

Chemical Property of Ethyl benzoylformate

Chemical Property:

• Appearance/Colour: clear colorless to greenish liquid
• Vapor Pressure: 0.0153mmHg at 25°C
• Melting Point: 97oC
• Refractive Index: 1.515-1.517
• Boiling Point: 256.499 °C at 760 mmHg
• Flash Point: 111.421 °C
• PSA: 43.37000
• Density: 1.132 g/cm³
• LogP: 1.43240
• Storage Temp.: Store below +30°C.
• Sensitive.: Moisture Sensitive
• Water Solubility.: Soluble in water 1143 mg/L @ 25°C .
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 178.062994177
• Heavy Atom Count: 13
• Complexity: 192

Purity/Quality:

99% ^*data from raw suppliers

Ethyl Benzoylformate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC(=O)C(=O)C1=CC=CC=C1
• Uses: Ethyl Benzoylformate is a general chemical reagent used in the preparation of diaminoethanediyl bismethylpyridinium salts for designing recyclable organocatalysts.

Technology Process of Ethyl benzoylformate

There total 186 articles about Ethyl benzoylformate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

(2,3-Dimethyl-benzo[g]indol-1-yl)-oxo-acetic acid ethyl ester (114570-16-0) + phenylmagnesium bromide → phenylglyoxylic acid ethyl ester (1603-79-8) + 2,3-dimethylbenz<6,7>indole (36729-21-2) + α-phenylbenzoin (4237-46-1) + benzil (134-81-6) + ethyl benzilate (52182-15-7)

Guidance literature:

In acetone; Product distribution;

DOI:10.1007/BF00475361

Reference yield: 54.0%

(1-hydroxy-2-oxo-2-phenylethyl)phosphonic acid diethyl ester (36126-89-3) → phenylglyoxylic acid ethyl ester (1603-79-8) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With tert.-butylhydroperoxide; In toluene; at 80 ℃; for 7h; Temperature;

DOI:10.1039/c5ob01615k

Reference yield: 53.0%

ethyl 2-phenylacetimidate hydrochloride (5442-34-2) → phenylglyoxylic acid ethyl ester (1603-79-8) + Ethyl 2-phenylethanoate (101-97-3)

Guidance literature:

ethyl 2-phenylacetimidate hydrochloride; With sodium hydrogencarbonate; In diethyl ether; at 0 ℃;

With pyridine; oxygen; copper diacetate; In chlorobenzene; at 90 ℃; for 20h; under 760.051 Torr; Sealed tube;

With hydrogenchloride; water; In chlorobenzene; Reagent/catalyst; Solvent; Sealed tube;

DOI:10.1021/acs.joc.6b02176

upstream raw materials:

2-oxo-propionic acid ethyl ester

ethyl 2-phenyl-2-aminoacetate

sodium ethanolate

benzoyl cyanide

Downstream raw materials:

2,4-diamino-6-phenyl-7(8H)-pteridinone

ethyl phenylhydrazono(phenyl)acetate

(2,4-dinitro-phenylhydrazono)-phenyl-acetic acid ethyl ester

O-ethyl-N-phenyloxoacetyl-isourea

Refernces

• 1、 Park, Heaweon,Bittner, Michael M.,Baus, Jacob S.,Lindeman, Sergey V.,Fiedler, Adam T.. "Fe(II) complexes that mimic the active site structure of acetylacetone dioxygenase: O2 and NO reactivity". . p. 10279 - 10289. Retrieved 2012.
• 2、 Mahmood, Syed J.,McLaughlin, Mike,Hossain, M. Mahmun. "A convenient new synthesis of aryl α-keto esters". . p. 2967 - 2972. Retrieved 1999.
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• 5、 Hoof,Sallmann,Herwig,Braun-Cula,Limberg. "O2 activation at a trispyrazolylborato nickel(II) malonato complex". . p. 16792 - 16795. Retrieved 2017.
• 6、 Takeda,T.,Mukaiyama,T.. "-". . p. 347 - 348. Retrieved 1976.
• 7、 Liu, Rongfang,Liu, Jialin,Cao, Jilei,Li, Ruifeng,Zhou, Rong,Qiao, Yan,Gao, Wen-Chao. "Chemo- And diastereoselective synthesis of pyrrolidines from aroylformates and δ-tosylamino enones via P(NMe2)3-mediated reductive amination/base-catalyzed michael addition cascade". . p. 6922 - 6926. Retrieved 2020.
• 8、 Kruse et al.. "-". . p. 5796. Retrieved 1954.
• 9、 Liu, Hong-Kun,Lei, Yi-Fei,Tian, Peng-Ju,Wang, Hui,Zhao, Xin,Li, Zhan-Ting,Zhang, Dan-Wei. "[Fe(bpy)3]2+-based porous organic polymers with boosted photocatalytic activity for recyclable organic transformations". supporting information. p. 6361 - 6367. Retrieved 2021/03/22.
• 10、 Khade, Vikas V.,Thube, Archana S.,Warghude, Prakash K.,Bhat, Ramakrishna G.. "DABCO mediated one pot synthesis of sulfoxonium ylides under blue LED". supporting information. . Retrieved 2021/07/25.