ethyl 6-cyanobenzothiophene-2-carboxylate

Base Information

• Chemical Name: ethyl 6-cyanobenzothiophene-2-carboxylate
• CAS No.: 105191-16-0
• Molecular Formula: C12H9NO2S
• Molecular Weight: 231.27000
• Mol file: 105191-16-0.mol

Synonyms:ethyl 6-cyanobenzothiophen-2-carboxylate;1H-Indazole-3-carboxylicacid,6-cyano-,ethyl ester;6-cyano-1H-indazole-3-carboxylic acid ethyl ester;

Chemical Property of ethyl 6-cyanobenzothiophene-2-carboxylate

Chemical Property:

• Vapor Pressure: 2.32E-06mmHg at 25°C
• Boiling Point: 392.3oC at 760 mmHg
• Flash Point: 191oC
• PSA: 78.33000
• Density: 1.31g/cm3
• LogP: 2.94968

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl 6-cyanobenzothiophene-2-carboxylate

There total 4 articles about ethyl 6-cyanobenzothiophene-2-carboxylate 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: 62.0%

3-chloro-4-formyl-benzonitrile (58588-64-0) + ethyl 2-sulfanylacetate (623-51-8) → 6-Cyanbenzothiophen-2-carbonsaeure-ethylester (105191-16-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 2h; Sealed tube;

DOI:10.1021/jacs.6b11188

Reference yield:

ethyl 6-nitrobenzo[b]thiophen-2-carboxylate (259150-06-6) → 6-Cyanbenzothiophen-2-carbonsaeure-ethylester (105191-16-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: H₂ / 10 percent Pd/C / ethanol / 15 h / 20 °C

2.1: 12N aq. HCl; NaNO₂ / tetrahydrofuran / 0.33 h / 2 - 3 °C

2.2: KCN / 3.5 h / 3 - 50 °C

With hydrogenchloride; hydrogen; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; ethanol; 1.1: Reduction / 2.1: Diazotization / 2.2: Sandmeyer reaction;

DOI:10.1248/cpb.47.1694

Reference yield:

copper(I) cyanide (544-92-3) + ethyl 6-amino-1-benzo[b]thiophene-2-carboxylate (947513-20-4) → 6-Cyanbenzothiophen-2-carbonsaeure-ethylester (105191-16-0)

Guidance literature:

ethyl 6-amino-1-benzo[b]thiophene-2-carboxylate; With hydrogenchloride; sodium nitrite; In tetrahydrofuran; at 2 - 3 ℃; for 0.333333h;

copper(I) cyanide; With potassium cyanide; at 3 - 50 ℃; for 3.5h;

DOI:10.1248/cpb.47.1694

upstream raw materials:

copper(I) cyanide

ethyl 6-amino-1-benzo[b]thiophene-2-carboxylate

ethyl 6-nitrobenzo[b]thiophen-2-carboxylate

3-chloro-4-formyl-benzonitrile

Downstream raw materials:

6-Cyanbenzothiophen-2-carbonsaeure

ethyl 6-[(1-ethoxy)iminomethyl]-2-benzothiophencarboxylate

t-butyl 4-[(6-cyanobenzo[b]thien-2-yl)carbonylamino]phenoxyacetate

{4-[(6-methylsulfanylcarbonimidoyl-benzo[b]thiophene-2-carbonyl)-amino]-phenoxy}-acetic acid tert-butyl ester