75998-29-7

Basic information

• Product Name: 3-CHLORO-6-METHOXYBENZO[B]THIOPHENE-2-CARBONYL CHLORIDE
• Synonyms: 3-chloro-6-methoxy-1-benzothiophene-2-carbonyl chloride;benzo[b]thiophene-2-carbonyl chloride, 3-chloro-6-methoxy-;3-chloro-6-methoxy-2-benzothiophenecarbonyl chloride;3-chloro-6-methoxy-benzothiophene-2-carbonyl chloride
• CAS NO: 75998-29-7
• Molecular Formula: C₁₀H₆Cl₂O₂S
• Molecular Weight: 261.13
• Mol File: 75998-29-7.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 379.969°C at 760 mmHg
• Flash Point: 183.599°C
• Appearance: /
• Density: 1.489g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.654
• CAS DataBase Reference: 3-CHLORO-6-METHOXYBENZO[B]THIOPHENE-2-CARBONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-6-METHOXYBENZO[B]THIOPHENE-2-CARBONYL CHLORIDE(75998-29-7)
• EPA Substance Registry System: 3-CHLORO-6-METHOXYBENZO[B]THIOPHENE-2-CARBONYL CHLORIDE(75998-29-7)

Safety Data

• RIDADR: UN3261
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 75998-29-7(Hazardous Substances Data)

Usage

General Description

3-CHLORO-6-METHOXYBENZO[B]THIOPHENE-2-CARBONYL CHLORIDE is a chemical compound with the molecular formula C12H7ClO2S. It is a carbonyl chloride derivative of benzo[b]thiophene, containing a chlorine atom and a methoxy group attached to the benzene ring. 3-CHLORO-6-METHOXYBENZO[B]THIOPHENE-2-CARBONYL CHLORIDE is commonly used in organic synthesis as a versatile building block in the preparation of pharmaceuticals, agrochemicals, and other fine chemicals. Its reactivity as a carbonyl chloride makes it a useful intermediate in the production of various functionalized benzo[b]thiophene derivatives. Additionally, it can serve as a valuable precursor for the synthesis of heterocyclic compounds with potential biological activity.

InChI:InChI=1/C10H6Cl2O2S/c1-14-5-2-3-6-7(4-5)15-9(8(6)11)10(12)13/h2-4H,1H3

Upstream product

• 5676-64-2 (Z)-3-(4-methoxyphenyl)acrylic acid 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 

Downstream Products

• 108144-50-9 3-Chloro-6-methoxy-N-(3-methoxyphenyl)benzothiophene-2-carboxamide 
• 108144-49-6 3-Chloro-6-methoxy-N-(2-methoxyphenyl)benzothiophene-2-carboxamide 
• 34576-80-2 3,7-dichloro-6-methoxybenzothiophene-2-carbonyl chloride 
• 108144-51-0 3-Chloro-6-methoxy-N-(4-methoxyphenyl)benzothiophene-2-carboxamide 
• 113424-98-9 3-Chloro-6-methoxy-N-phenylbenzothiophene-2-carboxamide 
• 216073-05-1 3-Chloro-6-methoxy-N-(2',3'-diphenyl-6'-indolyl)benzothiophene-2-carboxamide 
• 216073-06-2 10-Methoxy-2,3-diphenyl<1>benzothieno<2,3-c>pyrrolo<2,3-f>quinoline-7(6H)-one 
• 216073-09-5 7-Chloro-10-methoxy-2,3-diphenyl<1>benzothieno<2,3-c>pyrrolo<2,3-f>quinoline 
• 1133421-22-3 benzyl 3-benzyloxy-6-methoxy-1-benzo[b]thiophene-2-carboxylate 
• 1281988-28-0 2-(4-chlorophenylamino)-2-oxoethyl 3-chloro-6-methoxybenzo[b]thiophene-2-carbothioate 
• 1281988-30-4 2-(4-methoxyphenylamino)-2-oxoethyl 3-chloro-6-methoxybenzo[b]thiophene-2-carbothioate 
• 1281988-32-6 2-(4-bromophenylamino)-2-oxoethyl 3-ehloro-6-methoxybenzo[b]thiophene-2-carbothioate 

Relevant articles and documents

Construction of 2,3-disubstituted benzo[: B] thieno[2,3- d] thiophenes and benzo[4,5]selenopheno[3,2- b] thiophenes using the Fiesselmann thiophene synthesis

A series of 3-(hetero)aryl-substituted benzo[b]thieno[2,3-d]thiophenes, bearing various electron withdrawing groups at C-2 position of their scaffolds, were obtained using a convenient approach based on the Fiesselmann thiophene synthesis. To realize this strategy, the Friedel-Crafts acylation of (hetero)arenes with easily accessible 3-chlorobenzo[b]thiophene-2-carbonyl chlorides was initially performed to afford 3-chloro-2-(hetero)aroylbenzo[b]thiophenes. The latter ketones were treated either with methyl thioglycolate in the presence of DBU and calcium oxide powder or successively with sodium sulfide, an alkylating agent, containing methylene active component, and also DBU and calcium oxide, to form the desired benzo[b]thieno[2,3-d]thiophene derivatives. In addition, similar benzo[4,5]selenopheno[3,2-b]thiophene derivatives were prepared in the same manner using 3-bromobenzo[b]selenophen-2-yl substrates. The obtained functional derivatives of both benzo[b]thieno[2,3-d]thiophene and benzo[4,5]selenopheno[3,2-b]thiophene are of interest for further elaboration of organic semiconductor materials.

Design and Synthesis of Basic Selective Estrogen Receptor Degraders for Endocrine Therapy Resistant Breast Cancer

The clinical steroidal selective estrogen receptor (ER) degrader (SERD), fulvestrant, is effective in metastatic breast cancer, but limited by poor pharmacokinetics, prompting the development of orally bioavailable, nonsteroidal SERDs, currently in clinical trials. These trials address local breast cancer as well as peripheral metastases, but patients with brain metastases are generally excluded because of the lack of blood-brain barrier penetration. A novel family of benzothiophene SERDs with a basic amino side arm (B-SERDs) was synthesized. Proteasomal degradation of ERα was induced by B-SERDs that achieved the objectives of oral and brain bioavailability, while maintaining high affinity binding to ERα and both potency and efficacy comparable to fulvestrant in cell lines resistant to endocrine therapy or bearing ESR1 mutations. A novel 3-oxyazetidine side chain was designed, leading to 37d, a B-SERD that caused endocrine-resistant ER+ tumors to regress in a mouse orthotopic xenograft model.

Synthesis, characterization and structure activity relationship studies of benzo[b]thiophene derivatives as promising class of antimicrobial agents

Here we employed simple chemistry for the synthesis of a new potent series of benzo[b]thiophene containing 2-carbonylchlorides (1), 2-isopropyl carboxamides (2), 2-(piperidin-1-yl)-methanones (3) by nucleophilic chloro cyclocondensation of substituted-cin