10242-09-8

Basic information

• Product Name: 5-METHYL-BENZOFURAN-2-CARBOXYLIC ACID
• Synonyms: TIMTEC-BB SBB010591;5-METHYL-BENZOFURAN-2-CARBOXYLIC ACID;5-METHYL-1-BENZOFURAN-2-CARBOXYLIC ACID;AKOS BB623;5-methyl-1-benzofuran-2-carboxylic acid(SALTDATA: FREE);5-Methyl-2-benzofurancarboxylic acid;2-Benzofurancarboxylic acid, 5-Methyl-
• CAS NO: 10242-09-8
• Molecular Formula: C₁₀H₈O₃
• Molecular Weight: 176.17
• Mol File: 10242-09-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 238-240℃
• Boiling Point: 332.1 °C at 760 mmHg
• Flash Point: 154.7 °C
• Appearance: /
• Density: 1.303
• Storage Temp.: 2-8°C
• PKA: 3.16±0.30(Predicted)
• CAS DataBase Reference: 5-METHYL-BENZOFURAN-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-BENZOFURAN-2-CARBOXYLIC ACID(10242-09-8)
• EPA Substance Registry System: 5-METHYL-BENZOFURAN-2-CARBOXYLIC ACID(10242-09-8)

Safety Data

• Hazardous Substances Data: 10242-09-8(Hazardous Substances Data)

Usage

General Description

5-Methyl-benzofuran-2-carboxylic acid is a chemical compound with the molecular formula C9H8O3. It is a derivative of benzofuran, a heterocyclic compound containing a benzene ring fused to a furan ring. 5-METHYL-BENZOFURAN-2-CARBOXYLIC ACID is used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds. It is also known for its potential biological and pharmacological activities, including anti-inflammatory and antimicrobial properties. Additionally, 5-Methyl-benzofuran-2-carboxylic acid has shown promise in the development of novel drugs for the treatment of various diseases.

Upstream product

• 92-48-8 6-methylcoumarin 
• 88521-64-6 2-formyl-4-methylphenoxyacetic acid 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 685-87-0 Diethyl 2-bromomalonate 
• 53715-88-1 ethyl 5-methyl-1-benzofuran-2-carboxylate 
• 1159343-21-1 (2-(2,2-dibromovinyl)-4-methylphenol) 
• 13939-06-5 molybdenum hexacarbonyl 
• 1204351-35-8 2-(2-formyl-4-methylphenoxy)acetonitrile 
• 1210226-88-2 C₁₄H₁₆O₃ 
• 13257-19-7 5-chloromethyl-benzofuran-2-carboxylic acid ethyl ester 
• 3199-61-9 ethyl coumarilate 
• 88521-73-7 ethyl 2-(2-formyl-4-methylphenoxy)acetate 

Downstream Products

• 312607-99-1 5-methyl-2,3-dihydrobenzofuran-2-carboxylic acid 
• 82788-34-9 methyl 5-methylbenzofuran-2-carboxylate 

Relevant articles and documents

Efficient synthesis of a benzo[b]furan building block

Unexpected difficulty in the conversion of a bromobenzofuran to the corresponding formylbenzofuran led us to develop a new synthesis for 5-formylbenzo[b]furan-2-carbonitrile (1). Copyright

Synthesis and biological evaluation of novel shikonin-benzo[b]furan derivatives as tubulin polymerization inhibitors targeting the colchicine binding site

A novel series of shikonin-benzo[b]furan derivatives were designed and synthesized as tubulin polymerization inhibitors, and their biological activities were evaluated. Most compounds revealed the comparable anti-proliferation activities against the cancer cell lines to that of shikonin and simultaneously low cytotoxicity to non-cancer cells. Among them, compound 6c displayed powerful anti-cancer activity with the IC50 value of 0.18 μM against HT29 cells, which was significantly better than that of the reference drugs shikonin and CA-4. What's more, 6c could inhibit tubulin polymerization and compete with [3H] colchicine in binding to tubulin. Further biological studies depicted that 6c can induce cell apoptosis and cell mitochondria depolarize, regulate the expression of apoptosis related proteins in HT29 cells. Besides, 6c actuated the HT29 cell cycle arrest at G2/M phase, and influenced the expression of the cell-cycle related protein. Moreover, 6c displayed potent inhibition on cell migration and tube formation that contributes to the antiangiogenesis. These results prompt us to consider 6c as a potential tubulin polymerization inhibitor and is worthy for further study.

Catalytic Asymmetric Dearomatization by Visible-Light-Activated [2+2] Photocycloaddition

A novel method for the catalytic asymmetric dearomatization by visible-light-activated [2+2] photocycloaddition with benzofurans and one example of a benzothiophene is reported, thereby providing chiral tricyclic structures with up to four stereocenters including quaternary stereocenters. The benzofurans and the benzothiophene are functionalized at the 2-position with a chelating N-acylpyrazole moiety which permits the coordination of a visible-light-activatable chiral-at-rhodium Lewis acid catalyst. Computational molecular modeling revealed the origin of the unusual regioselectivity and identified the heteroatom in the heterocycle to be key for the regiocontrol.