13771-75-0

Basic information

• Product Name: 5-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID
• Synonyms: 5-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID;5-Chloro-1-benzothiophene-2-carboxylic acid;5-Chloro-1-benzothiophene-2-carboxylic acid, 2-Carboxy-5-chlorobenzo[b]thiophene;5-chloro-2-benzothiophenecarboxylic acid;5-chlorobenzothiophene-2-carboxylic acid;Benzo[b]thiophene-2-carboxylic acid, 5-chloro-
• CAS NO: 13771-75-0
• Molecular Formula: C₉H₅ClO₂S
• Molecular Weight: 212.65
• Mol File: 13771-75-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 256-258°
• Boiling Point: 408.6°C at 760 mmHg
• Flash Point: 200.9°C
• Appearance: /
• Density: 1.546g/cm³
• Vapor Pressure: 2.08E-07mmHg at 25°C
• Refractive Index: 1.719
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID(13771-75-0)
• EPA Substance Registry System: 5-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID(13771-75-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 13771-75-0(Hazardous Substances Data)

Usage

General Description

5-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID is a chemical compound with the molecular formula C9H5ClO2S. It is a heterocyclic compound containing a benzothiophene ring substituted with a carboxylic acid group and a chlorine atom. 5-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID is used in the synthesis of pharmaceuticals, agrochemicals, and materials science. It has properties that make it suitable for use as an intermediate in the production of various organic compounds. Additionally, it can also be used as a building block in the development of new chemical compounds for research purposes. Overall, 5-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID has versatile applications in the field of organic chemistry and is important for the development of new chemical products.

InChI:InChI=1/C9H5ClO2S/c10-6-1-2-7-5(3-6)4-8(13-7)9(11)12/h1-4H,(H,11,12)

Upstream product

• 20532-33-6 5-chlorobenzothiophene 
• 594-19-4 tert.-butyl lithium 
• 19492-99-0 methyl 5-methoxylbenzo[b]thiophene-2-carboxylate 
• 105728-90-3 2-fluoro-5-methoxybenzaldehyde 
• 6628-86-0 5-chloro-2-nitrobenzaldehyde 
• 96515-79-6 5-chloro-2-fluorobenzaldehyde 
• 35212-96-5 5-chloro-2-benzo[b]thiophenecarboxylic acid methyl ester 

Downstream Products

• 13771-97-6 C₉H₄Cl₂OS 

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.

Discovery of fluorescent coumarin-benzo[b]thiophene 1, 1-dioxide conjugates as mitochondria-targeting antitumor STAT3 inhibitors

STAT3 has been extensively studied as a potential antitumor target. Though studies on regulating STAT3 mainly focus on the inhibition of STAT3 phosphorylation at Tyr705 residue, the phosphorylation at Ser727 residue of STAT3 protein is also closely associated with the mitochondrial import of STAT3 protein. N, N-diethyl-7-aminocoumarin is a fluorescent mitochondria-targeting probe. In this study, a series of STAT3 inhibitors were developed by connecting N, N-diethyl-7-aminocoumarin fluorophore with benzo [b]thiophene 1, 1-dioxide moiety. All designed compounds displayed potent anti-proliferative activity against cancer cells. The representative compound 7a was mainly accumulated in mitochondria visualized by its fluorescence. STAT3 phosphorylation was inhibited by compound 7a at both Tyr705 and Ser727 residues. Compound 7a inhibited STAT3 phosphorylation whereas had no influence on the phosphorylation levels of STAT1, JAK2, Src and Erk1/2, indicating good selectivity of compound 7a. Moreover, compound 7a down-regulated the expression of STAT3 target genes Bcl-2 and Cyclin D1, increased ROS production and remarkably reduced the mitochondrial membrane potential to induce mitochondrial apoptotic pathway. Furthermore, compound 7a in vivo suppressed breast cancer 4T1 implanted tumor growth. Taken together, these results highlighted that compound 7a might be a promising mitochondria-targeting STAT3 inhibitor for cancer therapy.

GEMINAL SUBSTITUTED QUINUCLIDINE AMIDE COMPOUNDS AS AGONISTS OF ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTORS

The present invention relates to novel geminal substituted quinuclidine amide compounds, and pharmaceutical compositions of the same, that are suitable as agonists or partial agonists of α7- nAChR, and methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering the compound or composition to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.