23046-02-8

Basic information

• Product Name: 5-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID
• Synonyms: 5-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID;5-METHOXY-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID;Benzo[b]thiophene-2-carboxylic acid, 5-Methoxy-
• CAS NO: 23046-02-8
• Molecular Formula: C₁₀H₈O₃S
• Molecular Weight: 208.23
• Mol File: 23046-02-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 215-216 °C(Solv: acetic acid (64-19-7))
• Boiling Point: 410 °C at 760 mmHg
• Flash Point: 201.8 °C
• Appearance: /
• Density: 1.392 g/cm³
• Vapor Pressure: 1.86E-07mmHg at 25°C
• Refractive Index: 1.673
• Storage Temp.: 2-8°C
• PKA: 3.42±0.30(Predicted)
• CAS DataBase Reference: 5-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID(23046-02-8)
• EPA Substance Registry System: 5-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID(23046-02-8)

Safety Data

• Hazardous Substances Data: 23046-02-8(Hazardous Substances Data)

Usage

General Description

5-Methoxy-Benzo[b]thiophene-2-Carboxylic Acid is a chemical compound that belongs to a group of organic substances identified as benzothiophenes which consist of a benzene fused to a thiophene ring. It has a methoxy group (-OCH3) attached to the fifth carbon of the benzothiophene ring and a carboxylic acid group (-COOH) attached to the second carbon. 5-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID is used in a variety of scientific and industrial applications. However, specific details about its uses, hazards, and toxicity are limited which implies the need for comprehensive studies to explore its properties and applications.

InChI:InChI=1/C10H8O3S/c1-13-7-2-3-8-6(4-7)5-9(14-8)10(11)12/h2-5H,1H3,(H,11,12)

Upstream product

• 1010456-51-5 (2Z)-2-mercapto-3-(3-methoxyphenyl)-2-propenoic acid 
• 91715-52-5 β-(3-methoxyphenyl)-α-mercaptoacryIic acid 
• 19492-99-0 methyl 5-methoxylbenzo[b]thiophene-2-carboxylate 
• 105728-90-3 2-fluoro-5-methoxybenzaldehyde 
• 40862-88-2 5-methoxybenzo[b]thiophene-2-carboxylic acid ethyl ester 

Downstream Products

• 1010456-27-5 C₁₈H₁₅F₃N₂O₄S₂ 
• 19492-99-0 methyl 5-methoxylbenzo[b]thiophene-2-carboxylate 
• 20532-30-3 5-methoxybenzothiophene 
• 1300088-06-5 5-(methyloxy)-N-(1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl)-1-benzothiophene-2-carboxamide 

Relevant articles and documents

Development of Selective Clk1 and -4 Inhibitors for Cellular Depletion of Cancer-Relevant Proteins

In cancer cells, kinases of the Clk family control the supply of full-length, functional mRNAs coding for a variety of proteins essential to cell growth and survival. Thus, inhibition of Clks might become a novel anticancer strategy, leading to a selective depletion of cancer-relevant proteins after turnover. On the basis of a Weinreb amide hit compound, we designed and synthesized a diverse set of methoxybenzothiophene-2-carboxamides, of which the N-benzylated derivative showed enhanced Clk1 inhibitory activity. Introduction of a m-fluorine in the benzyl moiety eventually led to the discovery of compound 21b, a potent inhibitor of Clk1 and -4 (IC50 = 7 and 2.3 nM, respectively), exhibiting an unprecedented selectivity over Dyrk1A. 21b triggered the depletion of EGFR, HDAC1, and p70S6 kinase from the cancer cells, with potencies in line with the measured GI50 values. In contrast, the cellular effects of congener 21a, which inhibited Clk1 only weakly, were substantially lower.

Benzo[b]thiophene-2-carboxamide derivatives as potent urotensin-II receptor antagonists

Members of a series of benzo[b]thiophene-2-carboxamide derivatives, possessing an N-(1-(3-bromo-4-(piperidin-4-yloxy)benzyl)piperidin-4-yl) group, were synthesized and evaluated as urotensin-II receptor antagonists. The results show that these substances have potent UT binding affinities. Observations made in a systematic SAR investigation of the effects of a variety of substituents (R1and R2) at the 5- and 6-positions in the benzo[b]thiophene-2-carboxamide moiety on UT binding affinities led to identification of the 5-cyano analog 7f as a highly potent UT antagonist with an IC50value of 25?nM. Despite having a good metabolic stability, 7f is a potent inhibitor of CYP isozyme and displays an unsuitable PK profile.

Hydroxybenzothiophene ketones are efficient pre-mRNA splicing modulators due to dual inhibition of Dyrk1A and Clk1/4

Dysregulated usage of pre-mRNA splicing sites contributes to the progression of cancer, neurodegenerative diseases, and viral infections. Serine/arginine-rich (SR) proteins play major roles in the splice site recognition and are largely regulated by phosp