19075-59-3

Basic information

• Product Name: Benzo[b]thiophene-2-carboxylic acid, 7-bromo-
• Synonyms: Benzo[b]thiophene-2-carboxylic acid, 7-bromo-;7-Bromo-1-benzothiophene-2-carboxylic acid;7-broMo-Benzo[b]thiophene-2-carboxylic acid;7-Bromo-2-carboxybenzo[b]thiophene, 7-Bromo-1-benzothiophene-2-carboxylic acid;7-Bromobenzo[b]thiophene-2-carboxylic acid 95+%;7-Bromobenzothiophene-2-carboxylic acid
• CAS NO: 19075-59-3
• Molecular Formula: C9H5BrO2S
• Molecular Weight: 257
• Mol File: 19075-59-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 429.7°C at 760 mmHg
• Flash Point: 213.7°C
• Appearance: /
• Density: 1.813g/cm³
• Vapor Pressure: 3.8E-08mmHg at 25°C
• Refractive Index: 1.738
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: Benzo[b]thiophene-2-carboxylic acid, 7-bromo-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzo[b]thiophene-2-carboxylic acid, 7-bromo-(19075-59-3)
• EPA Substance Registry System: Benzo[b]thiophene-2-carboxylic acid, 7-bromo-(19075-59-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 19075-59-3(Hazardous Substances Data)

Usage

General Description

Benzo[b]thiophene-2-carboxylic acid, 7-bromo- is a chemical compound that belongs to the thiophene class of organic compounds. It is specifically a derivative of benzo[b]thiophene carboxylic acid with a bromine atom at the 7th position. Benzo[b]thiophene-2-carboxylic acid, 7-bromo- is used in the synthesis of various pharmaceuticals and agrochemicals due to its unique chemical properties and structural features. It is also utilized in the development of materials and dyes. Additionally, its presence in nature and potential environmental impact is a subject of ongoing research and study.

InChI:InChI=1/C9H5BrO2S/c10-6-3-1-2-5-4-7(9(11)12)13-8(5)6/h1-4H,(H,11,12)

Upstream product

• 149947-15-9 3-bromo-2-fluorobenzaldehyde 
• 2365-48-2 Methyl thioglycolate 
• 550998-53-3 methyl 7-bromobenzo[b]thiophene-2-carboxylate 
• 1355171-39-9 ethyl 7-bromobenzo[b]thiophene-2-carboxylate 
• 1072-85-1 o-fluorobromobenzene 

Downstream Products

• 547766-28-9 7-Bromo-1-benzothiophen-2-amine 
• 1171926-64-9 (7-bromo-1-benzothiophen-2-yl)methanol 
• 1207965-14-7 N-(2-hydroxyethyl)-3-{2-[3-(trifluoromethyl)benzyl]-1-benzothiophen-7-yl}benzamide 
• 1207965-12-5 N-(2-amino-2-oxoethyl)-3-{2-[3-(trifluoromethyl)benzyl]-1-benzothiophen-7-yl}benzamide 
• 1207965-13-6 N-(2-methoxyethyl)-3-{2-[3-(trifluoromethyl)benzyl]-1-benzothiophen-7-yl}benzamide 
• 1207965-40-9 3-[2-(3-chloro-5-fluorobenzyl)-1-benzothiophen-7-yl]-N-(2-methoxyethyl)benzamide 
• 1207970-52-2 ethyl 3-[2-(Hydroxymethyl)-1-benzothiophen-7-yl]benzoate 
• 1207970-63-5 ethyl 3-[2-(bromomethyl)-1-benzothiophen-7-yl]benzoate 
• 1613391-10-8 C₂₃H₁₅F₃O₂S 
• 1207970-84-0 ethyl 3-{2-[3-(trifluoromethyl)benzyl]-1-benzothiophen-7-yl}benzoate 
• 1423-61-6 7-bromobenzo(b)thiophene 

Relevant articles and documents

Design, synthesis, and biological evaluation of benzo[b]thiophene 1,1-dioxide derivatives as potent STAT3 inhibitors

As a member of the signal transducer and activator of transcription (STAT) family, STAT3 plays a critical role in several biological pathways such as cell proliferation, migration, survival, and differentiation. Due to abnormal continuous activation in tumors, inhibition of STAT3 has emerged as an attractive approach for the treatment of various cancer cells. Herein, we report a series of novel STAT3 inhibitors based on benzo[b]thiophene 1,1-dioxide scaffold and evaluated their anticancer potency. Among them, compound 8b exhibited the best activity against cancer cells. Compound 8b induced apoptosis and blocked the cell cycle. Meanwhile, 8b reduced intracellular ROS content and caused the loss of mitochondrial membrane potential. Further research revealed that 8b significantly blocked STAT3 phosphorylation and STAT3-dependent dual-luciferase reporter gene experiments showed that compound 8b has a marked inhibition of STAT3-mediated Firefly luciferase activity. Molecular modeling studies revealed compound 8b occupied the pocket well with the SH2 domain in a favorable conformation.

Antagonizing STAT3 activation with benzo[b]thiophene 1, 1-dioxide based small molecules

STAT3 is an attractive therapeutic target for cancer therapy. However, due to low potency or poor druggability, none of its inhibitors are clinically available. Herein, a series of aminobenzo[b]thiophene 1, 1-dioxides with good drug-likeness properties were designed, synthesized and evaluated as STAT3 inhibitors. Most of them exhibited higher antitumor activity than the small-molecule STAT3 inhibitor, Stattic. Compound 15 was the most potent and had an IC50range in 0.33–0.75?μM in various cancer cell lines. The overexpressed and IL-6 induced phosphorylation levels of STAT3 were both inhibited by 15 without influencing the phosphorylation levels of the upstream kinases Src and Jak2. 15 also suppressed the expressions of STAT3 downstream gene, Bcl-2. 15 effectively increased the ROS levels of cancer cells, induced cancer cell apoptosis and abolished the colony formation ability of cancer cells without affecting bypass kinase p-Erk. Furthermore, 15 in?vivo induced significant antitumor responses, and exhibited less toxicity than Doxorubicin. Together, this study described a class of new STAT3 inhibitors as antitumor agents.

METHOD FOR PROMOTING PLANT GROWTH

The present invention provides a method for promoting plant growth, which comprises treating a plant with at least one compound selected from a group consisting of a compound represented by the following Formula (1): and an agriculturally acceptable salt thereof, provided that a method for promoting plant growth which comprises treating plants with a compound corresponding to any one of the following (1) to (5) and an agriculturally acceptable salt thereof is excluded: (1) 4-(Trifluoromethyl)benzo[b]thiophene-2-carboxylic acid, (2) 5-(Trifluoromethyl)benzo[b]thiophene-2-carboxylic acid, (3) 6-(Trifluoromethyl)benzo[b]thiophene-2-carboxylic acid, (4) 7-(Trifluoromethyl)benzo[b]thiophene-2-carboxylic acid, and (5) Benzo[b]thiophene-2-carboxylic acid.