21211-22-3

Basic information

• Product Name: 3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLIC ACID
• Synonyms: 3-CHLORO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID;3-CHLORO-2-BENZO[B]THIOPHENE CARBOXYLIC ACID;AKOS BBB/202;AKOS B000001;AKOS AU36-M200;BUTTPARK 30\06-07;ART-CHEM-BB B000001;ASISCHEM N48972
• CAS NO: 21211-22-3
• Molecular Formula: C₉H₅ClO₂S
• Molecular Weight: 212.65
• EINECS: -0
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzothiophenes;BenzothiophenesHeterocyclic Building Blocks;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 21211-22-3.mol

Chemical Properties

• Melting Point: 268-272 °C(lit.)
• Boiling Point: 395.1 °C at 760 mmHg
• Flash Point: 192.8 °C
• Appearance: /
• Density: 1.546 g/cm³
• Vapor Pressure: 5.94E-07mmHg at 25°C
• Refractive Index: 1.719
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 2.27±0.30(Predicted)
• BRN: 1425602
• CAS DataBase Reference: 3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLIC ACID(21211-22-3)
• EPA Substance Registry System: 3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLIC ACID(21211-22-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 21211-22-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Chlorobenzo[b]thiophene-2-carboxylic acid is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique chemical structure allows it to be a valuable building block in the creation of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
3-Chlorobenzo[b]thiophene-2-carboxylic acid is used as a key component in the synthesis of various chemical compounds, such as:
1. 5-(3-chlorobenzo[b]thiophen-2-yl)-1,3,4-thiadiazol-2-ylamine, which is synthesized through condensation with thiosemicarbazide in the presence of POCl3. 3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLIC ACID may have potential applications in the development of new therapeutic agents.
2. 2-benzo[b]thiophen-2-yl-6-methylbenzo[d][1;3]oxazi-4-one, which is obtained by reacting 3-chlorobenzo[b]thiophene-2-carboxylic acid with 2-amino-5-methyl-benzoic acid in the presence of carbonyl diimidazole. 3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLIC ACID may be used in the development of new materials or pharmaceuticals.

InChI:InChI=1/C9H5ClO2S/c10-7-5-3-1-2-4-6(5)13-8(7)9(11)12/h1-4H,(H,11,12)

Upstream product

• 21815-91-8 3-chlorobenzo[b]thiophen-2-carbonyl chloride 
• 21211-07-4 3-chlorobenzo[b]thiophene-2-carboxylic acid methyl ester 
• 621-82-9 Cinnamic acid 
• 501-52-0 3-Phenylpropionic acid 

Downstream Products

• 21815-91-8 3-chlorobenzo[b]thiophen-2-carbonyl chloride 
• 229339-09-7 N-(4-chlorophenyl)-2-[((3-chlorobenzo[b]thien-2-yl)carbonyl)amino]-5-methylbenzamide 
• 216985-39-6 3-chloro-N-[2-[[(4-fluorophenyl)amino]carbonyl]-4-methylphenyl]benzo[b]thiophene-2-carboxamide 
• 124168-55-4 (3-chloro-benzo[b]thiophen-2-yl)-methanol 
• 1393456-37-5 C₁₉H₁₀ClF₃OS 

Relevant articles and documents

An efficient route to regioselective functionalization of benzo[b]thiophenes via palladium-catalyzed decarboxylative Heck coupling reactions: Insights from experiment and computation

Pd-catalyzed decarboxylative Heck-type coupling of 3-chlorobenzo[b]thiophene-2-carboxylic acids with styrenes have been developed as an efficient strategy for the construction of functionalized benzo[b]thiophenes. Theoretical analysis shows that AgCl generated during the reaction, instead of Pd, π-coordinates with the carboxyl O atom, making easy the rate-determining CO2 dissociation. The divergent reactivities of the Cl-substituted and H-substituted 3-benzo[b]thiophene-2-carboxylic acids are mainly due to the presence of the Cl substituent, which reduces the adjacent π-π interplay, thereby significantly contributing to decarboxylation. Therefore, the presence of both AgCl and the Cl substituent are of key importance in ensuring the occurrence of the reaction under the given conditions.

Agents and methods for treating ischemic and other diseases

This invention relates to compounds that modulate TRPM7 protein activity and use of the same for treatment or prophylaxis of ischemia, cancer, pain or glaucoma.

Synthesis, characterization and biological activities of some new benzo[b]thiophene derivatives

Benzo[b]thiophene molecules are found to be important tools in synthetic medicinal chemistry. They are of current interest due to their wide spectrum of pharmacological properties. In view of the biological activities of benzo[b]thiophene containing molecules, in this present research work, we propose the synthesis of some new benzo[b]thiophene derivatives such as thiadiazoles, oxadiazoles, pyrazolin & diaryl pyrazoles starting from 3-chlorobenzo[b]thiophene-2-carboxyl chloride. These newly synthesized compounds were characterized by elemental analyses, I.R, NMR and Mass spectral studies. Some of the selected compounds were screened for their antibacterial, antifungal and anti-inflammatory studies. Many of the molecules were found to be potent.

Discovery of a new series of potent and selective linear tachykinin NK 2 receptor antagonists

Starting from 1 (MEN 14268), a selective tachykinin NK2 receptor antagonist with an interesting in vitro pharmacological profile, a family of numerous antagonists was obtained through an optimization process focused on iterated structural modifications. The effects of the introduction of a wide variety of substituents on the lipophilic aromatic part of the molecule and the modulation of the structural constraint through the insertion of different achiral α,α-dialkylamino acids were investigated. In particular, aromatic and benzofused heteroaromatic moieties were introduced at the pseudo-N-terminal residue to replace the 2-benzothiophene moiety, and a systematic investigation of the best positioning of substituents onto the aromatic platform was reported for the benzothiophene core. Studies on the modulation of the length and the rigidity of the hydrophilic pseudo-C-terminal pendant are presented. Many heteroaliphatic groups are well tolerated by the receptor in this part of the ligand. The product 48f (MEN15596), bearing a methyl substituent on the benzothiophene and a tetrahydropyranylmethylpiperidine pendant, was finally selected for its good in vivo activity after intravenous, intraduodenal, and oral administration in guinea pigs.

SYNTHESIS AND SOME TRANSFORMATIONS OF BENZOTHIOPHENE DERIVATIVES

A number of 3-chloro-2-chlorocarbonylbenzothiophenes with alkyl substituents in various positions of the benzene ring were synthesized by arylation of acrylic acid with the corresponding alkyl-substituted iodobenzenes under the influence of catalytic amounts of palladium acetate and subsequent oxidation of the resulting arylacrylic acids with thionyl chloride.Replacement of the pyridine added in the oxidation reaction by triethylbenzylammonium chloride led to substantial increases in the yields of the desired products.The possibility of conversionof the resulting benzothiophene derivatives to thiophene ring-unsubstituted benzothiophenes was shown in the case of 3-chloro-2-chlorocarbonylbenzothiophene as a result of successive saponification of the 2-chlorocarbonyl group, decarboxylation, and dechlorination.