22913-24-2

Basic information

• Product Name: METHYL BENZO[B]THIOPHENE-2-CARBOXYLATE
• Synonyms: RARECHEM AL BF 0483;METHYL BENZO[B]THIOPHENE-2-CARBOXYLATE;METHYL THIANAPHTHENE-2-CARBOXYLATE;BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER;BUTTPARK 86\18-02;AKOS 91623;Benzo[b]thiophene-2-carboxylic acid methyl ester~Methyl thianaphthene-2-carboxylate~Thianaphthene-2-carboxylic acid methyl ester;Benzothiophene-2-Carboxylic Acid Methyl Ester
• CAS NO: 22913-24-2
• Molecular Formula: C₁₀H₈O₂S
• Molecular Weight: 192.23
• EINECS: -0
• Mol File: 22913-24-2.mol
• Article Data: 29

Chemical Properties

• Melting Point: 70-74 °C
• Boiling Point: 304.586 °C at 760 mmHg
• Flash Point: 138.009 °C
• Appearance: /
• Density: 1.274 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: 2-8°C
• BRN: 142166
• CAS DataBase Reference: METHYL BENZO[B]THIOPHENE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL BENZO[B]THIOPHENE-2-CARBOXYLATE(22913-24-2)
• EPA Substance Registry System: METHYL BENZO[B]THIOPHENE-2-CARBOXYLATE(22913-24-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 22913-24-2(Hazardous Substances Data)

Usage

General Description

Methyl benzo[b]thiophene-2-carboxylate is a chemical compound with the molecular formula C12H10O2S. It is a methyl ester derivative of benzo[b]thiophene-2-carboxylic acid and is commonly used in the pharmaceutical and agrochemical industries as a building block for the synthesis of various organic compounds. This chemical is known for its stable and consistent properties, making it a valuable intermediate in the production of drugs and other bioactive molecules. It is also used in the development of new materials and research into the potential applications of its unique chemical structure.

InChI:InChI=1/C10H8O2S/c1-12-10(11)9-6-7-4-2-3-5-8(7)13-9/h2-6H,1H3

Upstream product

• 7342-85-0 2-chlorobenzo[b]thiophene 
• 201230-82-2 carbon monoxide 
• 67-56-1 methanol 
• 6314-28-9 benzo[b]thiophene-2-carboxylic acid 
• 55164-16-4 2,2'-dithiodibenzaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 39827-11-7 benzothiophene-2-carboxylic acid chloride 
• 186581-53-3 diazomethane 
• 74-88-4 methyl iodide 
• 124-38-9 carbon dioxide 
• 95-15-8 Benzo[b]thiophene 
• 62-53-3 aniline 
• 136-95-8 2-amino-benzthiazole 
• 2987-53-3 2-(Methylthio)aniline 

Downstream Products

• 17890-56-1 benzothiophene-2-methanol 
• 1320338-33-7 methyl 2-fluoro-3-oxo-2,3-dihydrobenzo[b]thiophene-2-carboxylate 
• 107943-78-2 benzo[b]thiophene-2-carboxylic acid-(2-chloro-anilide) 
• 107943-19-1 benzo[b]thiophene-2-carboxylic acid-(3-chloro-anilide) 
• 107943-20-4 benzo[b]thiophene-2-carboxylic acid-(4-chloro-anilide) 
• 6314-40-5 N-phenylbenzo[b]thiophene-2-carboxamide 

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.

Ag(I)-Catalyzed C-H Carboxylation of Thiophene Derivatives

CO2utilization is an attractive aspect as it allows the direct conversion of CO2into valuable chemicals. In this regard, direct incorporation of CO2into the C-H bond of heteroaromatic compounds is important due to the ubiquitous structural motifs of the heteroaromatic carboxylic acids. Herein, we report the Ag-catalyzed C-H carboxylation of thiophene derivatives. This new catalytic system involving a phosphine ligand and lithiumtert-butoxide enables the direct carboxylation of thiophenes under mild reaction conditions. Experimental studies revealed that the use oftert-butyl alkoxide is critical for the exergonic formation of an arylsilver intermediate, and the results were further supported by density functional theory calculations.

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.