Ethyl 2-oxo-2-(thiophen-3-yl)acetate

Base Information

• Chemical Name: Ethyl 2-oxo-2-(thiophen-3-yl)acetate
• CAS No.: 53091-09-1
• Molecular Formula: C₈H₈O₃S
• Molecular Weight: 184.216
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID10508123
• Nikkaji Number: J1.387.407G
• Wikidata: Q72477467
• Mol file: 53091-09-1.mol

Synonyms:53091-09-1;Ethyl thiophenene-3-glyoxylate;ethyl 2-oxo-2-(thiophen-3-yl)acetate;ethyl 2-oxo-2-thiophen-3-ylacetate;MFCD09801444;ethyl 3-thienylglyoxylate;ethyl thien-3-yl-glyoxylate;SCHEMBL3961016;Ethyl oxo(thiophen-3-yl)acetate;DTXSID10508123;SGCFFCMXADEZEU-UHFFFAOYSA-N;AKOS006328839;ethyl2-oxo-2-(thiophen-3-yl)acetate;FT-0713210;A851024

Chemical Property of Ethyl 2-oxo-2-(thiophen-3-yl)acetate

Chemical Property:

• Vapor Pressure: 0.00781mmHg at 25°C
• Refractive Index: 1.534
• Boiling Point: 268.2 °C at 760 mmHg
• Flash Point: 116 °C
• PSA: 71.61000
• Density: 1.253 g/cm³
• LogP: 1.49390
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 184.01941529
• Heavy Atom Count: 12
• Complexity: 191

Purity/Quality:

99% ^*data from raw suppliers

Ethylthiophenene-3-glyoxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=O)C1=CSC=C1

Technology Process of Ethyl 2-oxo-2-(thiophen-3-yl)acetate

There total 8 articles about Ethyl 2-oxo-2-(thiophen-3-yl)acetate 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: 68.0%

ethanol (64-17-5) + 3-(dimethylamino)-1-(thiophen-3-yl)prop-2-en-1-one (79571-33-8) → ethyl 2-oxo-2-(thiophen-3-yl)acetate (53091-09-1)

Guidance literature:

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

DOI:10.1039/c9gc01357a

Reference yield: 33.0%

1-(thiophen-3-yl)-ethanone (1468-83-3) + potassium ethyl xanthogenate (140-89-6) → ethyl 2-oxo-2-(thiophen-3-yl)acetate (53091-09-1)

Guidance literature:

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

DOI:10.1021/acs.joc.9b03272

Reference yield: 30.0%

tri-n-butyl(thien-3-yl)tin (119405-65-1) + Ethyl oxalyl chloride (4755-77-5) → ethyl 2-oxo-2-(thiophen-3-yl)acetate (53091-09-1)

Guidance literature:

In benzene; for 18h; Heating;

upstream raw materials:

3-thienyl lithium

oxalic acid diethyl ester

ethyl 2,5-dichloro-3-thienylglyoxylate

tri-n-butyl(thien-3-yl)tin

Downstream raw materials:

2-oxo-2-(thiophen-3-yl)acetic acid

Refernces

• 1、 Li, Bowen,Aliyu, Muinat A.,Gao, Zhenhua,Li, Tiejun,Dong, Wei,Li, Junchen,Shi, Enxue,Tang, Wenjun. "General Synthesis of Chiral α,α-Diaryl Carboxamides by Enantioselective Palladium-Catalyzed Cross-Coupling". supporting information. p. 4974 - 4978. Retrieved 2020/07/03.
• 2、 Wentzel, Bastienne B,Donners, Maurice P.J,Alsters, Paul L,Feiters, Martinus C,Nolte, Roeland J.M. "N-hydroxyphthalimide/cobalt(II) catalyzed low temperature benzylic oxidation using molecular oxygen". . p. 7797 - 7803. Retrieved 2007/10/03.