1134-00-5

Basic information

• Product Name: 5-CHLORO-3-METHYL-1-BENZOFURAN-2-CARBOXYLIC ACID
• Synonyms: 2-Benzofurancarboxylicacid, 5-chloro-3-Methyl-
• CAS NO: 1134-00-5
• Molecular Formula: C₁₀H₇ClO₃
• Molecular Weight: 210.62
• Mol File: 1134-00-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 362.8 °C at 760 mmHg
• Flash Point: 173.2 °C
• Appearance: /
• Density: 1.431 g/cm³
• Vapor Pressure: 6.74E-06mmHg at 25°C
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-CHLORO-3-METHYL-1-BENZOFURAN-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-3-METHYL-1-BENZOFURAN-2-CARBOXYLIC ACID(1134-00-5)
• EPA Substance Registry System: 5-CHLORO-3-METHYL-1-BENZOFURAN-2-CARBOXYLIC ACID(1134-00-5)

Safety Data

• Hazardous Substances Data: 1134-00-5(Hazardous Substances Data)

Usage

General Description

5-CHLORO-3-METHYL-1-BENZOFURAN-2-CARBOXYLIC ACID is a chemical compound with the molecular formula C10H7ClO3. It is a derivative of benzofuran, a heterocyclic compound containing a benzene ring fused to a furan ring. 5-CHLORO-3-METHYL-1-BENZOFURAN-2-CARBOXYLIC ACID is classified as a carboxylic acid due to the presence of a carboxyl group, which is a functional group containing a carbon atom doubly bonded to an oxygen atom and singly bonded to a hydroxyl group. The chlorine atom in its structure gives the compound its characteristic chlorinated properties. This chemical may be used in pharmaceutical research and drug development due to the potential biological activities associated with benzofuran derivatives, such as anti-inflammatory, antiviral, and anticancer properties.

InChI:InChI=1/C10H7ClO3/c1-5-7-4-6(11)2-3-8(7)14-9(5)10(12)13/h2-4H,1H3,(H,12,13)/p-1

Upstream product

• 100119-57-1 (2-acetyl-4-chlorophenoxy)acetic acid ethyl ester 
• 876-27-7 4-chlorophenyl acetate 
• 106-48-9 4-chloro-phenol 
• 77956-36-6 methyl 2-(2-acetyl-4-chlorophenoxy)acetate 
• 119138-73-7 ethyl 5-chloro-3-methylbenzofuran-2-carboxylate 
• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 21758-94-1 (2-acetyl-4-chlorophenoxy)acetic acid 

Relevant articles and documents

5-Chlorobenzofuran-2-carboxamides: From allosteric CB1 modulators to potential apoptotic antitumor agents

Cannabinoids as THC and the CB1 allosteric modulator CBD were reported to have antiproliferative activities with no reports for other CB1 allosteric modulators as the 5-chloroindole-2-carboxamide derivatives and their furan congeners. Based on the antiproliferative activity of two 5-chlorobenzofuran-2-carboxamide allosteric CB1 modulators, a series of novel derivatives was designed and synthesized. The synthesized compounds were tested in a cell viability assay using human mammary gland epithelial cell line (MCF-10A) where all the compounds exhibited no cytotoxic effects and more than 85% cell viability at a concentration of 50 μM. Some derivatives showed good antiproliferative activities against tumor cells as compounds 8, 15, 21 and 22. The most active compound 15 showed equipotent activity to doxorubicin. Compounds 7, 9, 15, 16, 21 and 22 increased the level of active caspase 3 by 4–8 folds, compared to the control cells in MCF-7 cell line and doxorubicin as a reference drug. Compounds 15 and 21, the most activecaspase-3 inducers, increase the levels of caspase 8 and 9 indicating activation of both intrinsic and extrinsic pathways and showed potent induction of Bax, down-regulation of Bcl-2 protein levels and over-expression of Cytochrome C levels in MCF-7 cell lines. Compound 15 exhibited cell cycle arrest at the Pre-G1 and G2/M phases in the cell cycle analysis of MCF-7 cell line. The drug Likeness profile of the synthesized compounds showed that all the compounds were predicted to have high oral absorption complying with different pharmacokinetics filters.

Discovery of potent myeloid cell leukemia 1 (Mcl-1) inhibitors using fragment-based methods and structure-based design

Myeloid cell leukemia 1 (Mcl-1), a member of the Bcl-2 family of proteins, is overexpressed and amplified in various cancers and promotes the aberrant survival of tumor cells that otherwise would undergo apoptosis. Here we describe the discovery of potent and selective Mcl-1 inhibitors using fragment-based methods and structure-based design. NMR-based screening of a large fragment library identified two chemically distinct hit series that bind to different sites on Mcl-1. Members of the two fragment classes were merged together to produce lead compounds that bind to Mcl-1 with a dissociation constant of 100 nM with selectivity for Mcl-1 over Bcl-xL and Bcl-2. Structures of merged compounds when complexed to Mcl-1 were obtained by X-ray crystallography and provide detailed information about the molecular recognition of small-molecule ligands binding Mcl-1. The compounds represent starting points for the discovery of clinically useful Mcl-1 inhibitors for the treatment of a wide variety of cancers.

Benzofuran Derivatives. Part 4. Synthesis of Benzofurans and 2,3,4,5-Tetrahydro-1-benzoxepin-3,5-diones

By treatment of ethyl 4- or 5-substituted 2-acetylphenoxyacetates 1 with potassium hydroxide in dry dioxane, benzofurans 2-7 and 2,3,4,5-tetrahydro-1-benzoxepin-3,5-diones 8 were obtained.The relative yields of benzofurans 2-7 and 2,3,4,5-tetrahydro-1-benzoxepin-3,5-diones 8 varied with the types of 4- or 5-substituents.The electron-donating 4-methoxyl group favored the formation of benzoxepins.On the other hand, electron-withdrawing substituents such as the 4-nitro group favored the formation of benzofurans.When esters 1 were treated with sodium amide,2,3-dihydrobenzofurans 2 were obtained exclusively regardless of 4- or 5-substituents.