146137-93-1

Basic information

• Product Name: 5-CYANO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER
• Synonyms: 5-CYANO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER
• CAS NO: 146137-93-1
• Molecular Formula: C₁₁H₇NO₂S
• Molecular Weight: 217.24
• Mol File: 146137-93-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 382.9°C at 760 mmHg
• Flash Point: 185.4°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 4.57E-06mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: 5-CYANO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CYANO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER(146137-93-1)
• EPA Substance Registry System: 5-CYANO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER(146137-93-1)

Safety Data

• Hazardous Substances Data: 146137-93-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H7NO2S/c1-14-11(13)10-5-8-4-7(6-12)2-3-9(8)15-10/h2-5H,1H3

Upstream product

• 1194-02-1 4-fluorobenzonitrile 
• 2365-48-2 Methyl thioglycolate 
• 2060-63-1 benzo[b]thiophene-5-carbonitrile 
• 124-38-9 carbon dioxide 
• 74-88-4 methyl iodide 
• 119072-55-8 tert-butylisonitrile 
• 146137-90-8 methyl 5-iodobenzo[b]thiophene-2-carboxylate 
• 146137-79-3 4-fluoro-3-formylbenzonitrile 

Downstream Products

• 154650-76-7 5-cyanobenzo[b]thiophene-2-carboxylic acid 
• 544694-79-3 4-{4-[(5-carbamimidoyl-benzo[b]thiophen-2-ylmethyl)-ethoxycarbonylmethanesulfonyl-amino]-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester 
• 364614-55-1 ((5-carbamimidoyl-benzo[b]thiophen-2-ylmethyl)-{4-[1-(1-imino-ethyl)-piperidin-4-yloxy]-phenyl}-sulfamoyl)-acetic acid ethyl ester 
• 544694-55-5 4-{4-[(5-carbamimidoyl-benzo[b]thiophen-2-ylmethyl)-methanesulfonyl-amino]-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester 
• 364614-57-3 2-[({4-[1-(1-imino-ethyl)-piperidin-4-yloxy]-phenyl}-methanesulfonyl-amino)-methyl]-benzo[b]thiophene-5-carboxamidine 

Relevant articles and documents

Design, synthesis, and biological activity evaluation of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives as broad-spectrum antifungal agents

To discover antifungal compounds with broad-spectrum and stable metabolism, a series of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives was designed and synthesized. Compounds A30-A34 exhibited excellent broad-spectrum antifungal activity against Candida albicans with MIC values in the range of 0.03–0.5 μg/mL, and against Cryptococcus neoformans and Aspergillus fumigatus with MIC values in the range of 0.25–2 μg/mL. In addition, compounds A31 and A33 showed high metabolic stability in human liver microsomes in vitro, with the half-life of 80.5 min and 69.4 min, respectively. Moreover, compounds A31 and A33 showed weak or almost no inhibitory effect on the CYP3A4 and CYP2D6. The pharmacokinetic evaluation in SD rats showed that compound A31 had suitable pharmacokinetic properties and was worthy of further study.

Benzo[b]thiophene-2-carboxamide derivatives as potent urotensin-II receptor antagonists

Members of a series of benzo[b]thiophene-2-carboxamide derivatives, possessing an N-(1-(3-bromo-4-(piperidin-4-yloxy)benzyl)piperidin-4-yl) group, were synthesized and evaluated as urotensin-II receptor antagonists. The results show that these substances have potent UT binding affinities. Observations made in a systematic SAR investigation of the effects of a variety of substituents (R1and R2) at the 5- and 6-positions in the benzo[b]thiophene-2-carboxamide moiety on UT binding affinities led to identification of the 5-cyano analog 7f as a highly potent UT antagonist with an IC50value of 25?nM. Despite having a good metabolic stability, 7f is a potent inhibitor of CYP isozyme and displays an unsuitable PK profile.

Synthesis of aryl nitriles by palladium-assisted cyanation of aryl iodides using tert-butyl isocyanide as cyano source

Abstract A palladium-catalyzed synthesis of aryl nitriles by the cyanation of aryl iodides with tert-butyl isocyanide as cyano source has been developed. This novel and efficient method avoids the use of toxic cyanides. The reaction is easy-to-handle and shows good functional group compatibility.