35212-96-5

Basic information

• Product Name: METHYL 5-CHLORO-1-BENZOTHIOPHENE-2-CARBOXYLATE
• Synonyms: METHYL 5-CHLORO-1-BENZOTHIOPHENE-2-CARBOXYLATE;Methyl 5-chlorobenzo[b]thiophene-2-carboxylate;5-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER;Benzo[b]thiophene-2-carboxylic acid, 5-chloro-, methyl ester;Methyl 5-Chloro-1-Benzothiophene-2-Carboxylate(WXC03947)
• CAS NO: 35212-96-5
• Molecular Formula: C10H7ClO2S
• Molecular Weight: 226.67938
• Mol File: 35212-96-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 113-115
• Boiling Point: 338.7 °C at 760 mmHg
• Flash Point: 158.6 °C
• Appearance: /
• Density: 1.391 g/cm³
• Vapor Pressure: 9.66E-05mmHg at 25°C
• Refractive Index: 1.646
• CAS DataBase Reference: METHYL 5-CHLORO-1-BENZOTHIOPHENE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 5-CHLORO-1-BENZOTHIOPHENE-2-CARBOXYLATE(35212-96-5)
• EPA Substance Registry System: METHYL 5-CHLORO-1-BENZOTHIOPHENE-2-CARBOXYLATE(35212-96-5)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 35212-96-5(Hazardous Substances Data)

Usage

Uses

Methyl 5-chlorobenzo[b]thiophene-2-carboxylate acts as a reagent in the synthesis and biological evaluation of amide-, urea- and thiourea-functionalized dipeptides as selective linear tachykinin NK2 receptor antagonists, preparation and SAR of benzothiophene carboxamides as urotensin-II receptor antagonists.

InChI:InChI=1/C10H7ClO2S/c1-13-10(12)9-5-6-4-7(11)2-3-8(6)14-9/h2-5H,1H3

Upstream product

• 20532-33-6 5-chlorobenzothiophene 
• 124-38-9 carbon dioxide 
• 74-88-4 methyl iodide 
• 2365-48-2 Methyl thioglycolate 
• 96515-79-6 5-chloro-2-fluorobenzaldehyde 
• 6628-86-0 5-chloro-2-nitrobenzaldehyde 

Downstream Products

• 13771-75-0 5-chloro-benzo(b)thiophene-2-carboxylic acid 
• 13771-71-6 2-Hydroxymethyl-5-chlor-benzothiophen 

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.

Direct Carboxylation of Electron-Rich Heteroarenes Promoted by LiO-tBu with CsF and [18]Crown-6

We herein demonstrate that the combination of LiO-tBu, CsF, and [18]crown-6 efficiently promotes the direct C?H carboxylation of electron-rich heteroarenes (benzothiophene, thiophene, benzofuran, and furan derivatives). A variety of functional groups, including methyl, methoxy, halo, cyano, amide, and keto moieties, are compatible with this system. The reaction proceeds via the formation of a tert-butyl carbonate species.

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.