6314-28-9

Basic information

• Product Name: Thianaphthene-2-carboxylic acid
• Synonyms: RARECHEM AL BE 0483;TIMTEC-BB SBB003763;THIANAPHTHENE-2-CARBOXYLIC ACID;BENZO[B]THIOPHENE-2-CARBOXYLIC ACID;BENZOTHIOPHENE-2-CARBOXYLIC ACID;BUTTPARK 86\18-03;AKOS 92498;1-BENZOTHIOPHENE-2-CARBOXYLIC ACID
• CAS NO: 6314-28-9
• Molecular Formula: C₉H₆O₂S
• Molecular Weight: 178.21
• EINECS: 1592732-453-0
• Product Categories: Sulphur Derivatives;Carboxylic Acids;Thiophenes & Benzothiophenes;Carboxylic Acids;Thiophenes & Benzothiophenes
• Mol File: 6314-28-9.mol
• Article Data: 36

Chemical Properties

• Melting Point: 238-243 °C
• Boiling Point: 280.44°C (rough estimate)
• Flash Point: 181.3 °C
• Appearance: off-white to yellowish-beige crystalline powder
• Density: 1.3242 (rough estimate)
• Vapor Pressure: 2.5E-06mmHg at 25°C
• Refractive Index: 1.5480 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 3.48±0.30(Predicted)
• Water Solubility: Soluble in ethanol, acetone and chloroform. Insoluble in water.
• Merck: 14,9345
• BRN: 124613
• CAS DataBase Reference: Thianaphthene-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Thianaphthene-2-carboxylic acid(6314-28-9)
• EPA Substance Registry System: Thianaphthene-2-carboxylic acid(6314-28-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36
• WGK Germany: 3
• Hazardous Substances Data: 6314-28-9(Hazardous Substances Data)

Usage

Chemical Properties

off-white to yellowish-beige crystalline powder

Uses

Thianaphthene-2-carboxylic acid may be used for the fabrication of carboxylated conducting polymer/CNTs (carbon nanotubes) composites thin films.

Synthesis Reference(s)

The Journal of Organic Chemistry, 21, p. 39, 1956 DOI: 10.1021/jo01107a007

General Description

Thianaphthene-2-carboxylic acid, a benzothiophene, is a heterocyclic sulfur compound. It undergoes degradation (23%) by employing a mixture of washed cells of Rhodococcus erythropolis DS-3 and Gordonia sp. C-6.

InChI:InChI=1/C9H6O2S/c10-9(11)8-5-6-3-1-2-4-7(6)12-8/h1-5H,(H,10,11)/p-1

Upstream product

• 22720-75-8 2-acetyl benzo[b]thiophene 
• 5416-07-9 3-phenyl-2-thioxopropanoic acid 
• 93655-62-0 α,α'-disulfanediyl-di-cinnamic acid 
• 29199-11-9 2-formylthiophenol 
• 79-11-8 chloroacetic acid 
• 95-15-8 Benzo[b]thiophene 
• 76-02-8 trifluoroacetyl chloride 
• 67-56-1 methanol 
• 7342-85-0 2-chlorobenzo[b]thiophene 
• 201230-82-2 carbon monoxide 
• 124-38-9 carbon dioxide 
• 109-72-8 n-butyllithium 
• 60-29-7 diethyl ether 
• 1195-14-8 2-Methylbenzothiophene 

Downstream Products

• 22913-24-2 methyl benzo[b]thiophene-2-carboxylate 
• 17890-56-1 benzothiophene-2-methanol 
• 27916-82-1 2,3-Dihydrobenzothiophene-2-carboxylic acid 
• 924605-12-9 [4-(2-Benzhydryloxy-ethyl)-piperazin-1-yl]-benzo[b]thiophen-2-yl-methanone 
• 3541-37-5 benzothiophene-2-carboxaldehyde 
• 95-15-8 Benzo[b]thiophene 

Relevant articles and documents

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Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer

The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.

Design, synthesis, and biological evaluation of benzo[b]thiophene 1,1-dioxide derivatives as potent STAT3 inhibitors

As a member of the signal transducer and activator of transcription (STAT) family, STAT3 plays a critical role in several biological pathways such as cell proliferation, migration, survival, and differentiation. Due to abnormal continuous activation in tumors, inhibition of STAT3 has emerged as an attractive approach for the treatment of various cancer cells. Herein, we report a series of novel STAT3 inhibitors based on benzo[b]thiophene 1,1-dioxide scaffold and evaluated their anticancer potency. Among them, compound 8b exhibited the best activity against cancer cells. Compound 8b induced apoptosis and blocked the cell cycle. Meanwhile, 8b reduced intracellular ROS content and caused the loss of mitochondrial membrane potential. Further research revealed that 8b significantly blocked STAT3 phosphorylation and STAT3-dependent dual-luciferase reporter gene experiments showed that compound 8b has a marked inhibition of STAT3-mediated Firefly luciferase activity. Molecular modeling studies revealed compound 8b occupied the pocket well with the SH2 domain in a favorable conformation.