Ethyl 4-cyanobenzoylformate

Base Information

• Chemical Name: Ethyl 4-cyanobenzoylformate
• CAS No.: 302912-31-8
• Molecular Formula: C11H9NO3
• Molecular Weight: 203.197
• DSSTox Substance ID: DTXSID30398942
• Nikkaji Number: J2.170.625F
• Wikidata: Q72473886
• Mol file: 302912-31-8.mol

Synonyms:Ethyl 4-cyanobenzoylformate;302912-31-8;ethyl 2-(4-cyanophenyl)-2-oxoacetate;MFCD01319614;ethyl (4-cyanophenyl)(oxo)acetate;4-Cyano-phenylglyoxylic acid ethyl ester;Ethyl2-(4-cyanophenyl)-2-oxoacetate;4-Cyano-a-oxo-benzeneacetic acid ethyl ester;Ethyl-4-Cyanobenzoylformate;AMY695;SCHEMBL1124607;DTXSID30398942;MGBZXMQPYAYPIQ-UHFFFAOYSA-N;Ethyl 4-cyanobenzoylformate, 95%;CMA91231;4-Cyano-phenylglyoxylicacidethylester;AKOS005255461;CS-W022644;DS-4984;SY024450;FT-0653925;(4-cyano-phenyl)-oxo-acetic acid ethyl ester;A23226;alpha-Oxo-4-cyanobenzeneacetic acid ethyl ester;F11929;Benzeneacetic acid, 4-cyano-alpha-oxo-, ethyl ester;J-017881;J-521005

Chemical Property of Ethyl 4-cyanobenzoylformate

Chemical Property:

• Vapor Pressure: 4.43E-05mmHg at 25°C
• Refractive Index: n20/D 1.537(lit.)
• Boiling Point: 350.3 °C at 760 mmHg
• Flash Point: 153 °C
• Density: 1.22 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 203.058243149
• Heavy Atom Count: 15
• Complexity: 294

Purity/Quality:

97% ^*data from raw suppliers

Ethyl 4-cyanobenzoylformate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=O)C1=CC=C(C=C1)C#N

Technology Process of Ethyl 4-cyanobenzoylformate

There total 6 articles about Ethyl 4-cyanobenzoylformate 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: 82.0%

4-cyanophenyl methyl ketone (1443-80-7) + potassium ethyl xanthogenate (140-89-6) → ethyl-4-cyanobenzoylformate (302912-31-8)

Guidance literature:

With iodine; dimethyl sulfoxide; In water; at 80 ℃; for 12h; Schlenk technique;

DOI:10.1021/acs.joc.9b03272

Reference yield: 76.0%

ethyl 2-(4-cyanophenyl)-2-diazoacetate → ethyl-4-cyanobenzoylformate (302912-31-8)

Guidance literature:

With tris(pentafluorophenyl)borate; dimethyl sulfoxide; at 90 ℃; for 12h; Inert atmosphere;

DOI:10.1002/adsc.202101336

Reference yield: 74.0%

ethanol (64-17-5) + C13H13NO → ethyl-4-cyanobenzoylformate (302912-31-8)

Guidance literature:

With acetic acid; Rose Bengal lactone; at 20 ℃; for 24h; chemoselective reaction; Molecular sieve; Photolysis;

DOI:10.1039/c9gc01357a

upstream raw materials:

4-ethylbenzonitrile

ethyl acetate

4-bromobenzenecarbonitrile

oxalic acid diethyl ester

Downstream raw materials:

(R/S)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide

(R/S)-N-(2-(ethylamino)-2-oxoethyl)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide

(R/S)-N-ethyl-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide