7312-11-0

Basic information

• Product Name: METHYL 5-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE
• Synonyms: METHYL 5-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE;5-Bromo-benzothiophene-2-carboxylic acid;5-BROMO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER;Benzo[b]thiophene-2-carboxylic acid, 5-broMo-, Methyl ester;5-BroMobenzothiophene-2-carboxylic Acid Methyl Ester;Methyl 5-BroMobenzo[b]thiophen-2-carboxylate;Methyl 5-BroMobenzo[b]thiophene-2- carboxylate;3T-1185
• CAS NO: 7312-11-0
• Molecular Formula: C₁₀H₇BrO₂S
• Molecular Weight: 271.13
• Product Categories: Aromatics;Heterocycles;Sulfur & Selenium Compounds
• Mol File: 7312-11-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 110 °C
• Boiling Point: 358.9 °C at 760 mmHg
• Flash Point: 170.8 °C
• Appearance: /
• Density: 1.622 g/cm³
• Vapor Pressure: 2.47E-05mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: METHYL 5-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 5-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE(7312-11-0)
• EPA Substance Registry System: METHYL 5-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE(7312-11-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 7312-11-0(Hazardous Substances Data)

Usage

Description

Methyl 5-bromo-1-benzothiophene-2-carboxylate, also known as 5-Bromobenzothiophene-2-carboxylic acid methyl ester, is an organic compound with a molecular structure that features a benzene ring fused to a thiophene ring, with a bromine atom at the 5-position and a carboxylate ester group at the 2-position. Methyl 5-bromo-1-benzothiophene-2-carboxylate is characterized by its potential applications in the pharmaceutical industry, particularly in the development of novel therapeutic agents for neurological and neurodegenerative diseases.

Uses

Used in Pharmaceutical Industry:
Methyl 5-bromo-1-benzothiophene-2-carboxylate is used as a key intermediate in the synthesis of new derivatives of (heterocycle-tetrahydropyridine)-(piperazinyl)-1-alkanone and (heterocycle-dihydropyrrolidine)-(piperazinyl)-1-alkanone. These derivatives have been identified as potential p75 neurotrophin receptor ligands, which can be utilized for the treatment of various neurological and neurodegenerative diseases.
Methyl 5-bromo-1-benzothiophene-2-carboxylate's unique structure and functional groups make it a valuable building block for the development of novel therapeutic agents. By targeting the p75 neurotrophin receptor, these derivatives have the potential to modulate cellular signaling pathways and provide therapeutic benefits for patients suffering from neurological and neurodegenerative conditions, such as Alzheimer's disease, Parkinson's disease, and multiple sclerosis.

InChI:InChI=1/C10H7BrO2S/c1-13-10(12)9-5-6-4-7(11)2-3-8(6)14-9/h2-5H,1H3

Upstream product

• 2365-48-2 Methyl thioglycolate 
• 93777-26-5 5-bromo-2-fluorobenzaldehyde 
• 4923-87-9 5-bromobenzo[b]thiophene 
• 124-38-9 carbon dioxide 
• 74-88-4 methyl iodide 

Downstream Products

• 7312-10-9 5-bromo-1-benzothiophene-2-carboxylic acid 
• 146137-90-8 methyl 5-iodobenzo[b]thiophene-2-carboxylate 
• 924869-09-0 methyl 5-(4-methoxyphenyl)benzo[b]thiophene-2-carboxylate 
• 154649-85-1 methyl 5-phenylbenzo[b]thiophene-2-carboxylate 
• 1252780-49-6 5-phenylbenzo[b]thiophene-2-carboxylic acid 
• 1252780-50-9 3-fluoro-5-phenyl-benzo[b]thiophene-2-carboxylic acid 
• 1252781-80-8 3-fluoro-5-phenyl-benzo[b]thiophene-2-carbonyl chloride 
• 1373524-56-1 (3S)-N-{1-[(3-Fluoro-5-phenyl-1-benzothiophen-2-yl)carbonyl]azetidin-3-yl}-1-(phenylcarbonyl)pyrrolidin-3-amine 
• 907945-15-7 5-(4-chlorophenyl)benzo[b]thiophene-2-carboxylic acid 
• 907945-17-9 5-(4-trifluoromethylphenyl)benzo[b]thiophene-2-carboxylic acid 

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.

HDAC inhibitor and preparation method and application thereof

The present invention discloses a compound represented by a formula I, a stereoisomer thereof, and a pharmaceutically acceptable salt thereof. The invention further relates to a pharmaceutical composition containing the compound shown in the formula I and application of the compound in preparation of HDAC inhibitor drugs. The compound or the pharmaceutical composition thereof can be used for treating cell proliferation diseases, autoimmune diseases, inflammation, neurodegenerative diseases or viral diseases.

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.