2766-74-7

Basic information

• Product Name: 5-Chlorothiophene-2-sulfonyl chloride
• Synonyms: TIMTEC-BB SBB003378;5-CHLORO-2-THIENYLSULFONYL CHLORIDE;5-CHLORO-2-THIOPHENESULFONYL CHLORIDE;5-CHLOROTHIOPHENE-2-SULFONYL CHLORIDE;5-CHLOROTHIOPHENE-2-SULPHONYL CHLORIDE;5-CHLOROTHIOPHENESULPHONYL CHLORIDE;AKOS B019398;ART-CHEM-BB B019398
• CAS NO: 2766-74-7
• Molecular Formula: C₄H₂Cl₂O₂S₂
• Molecular Weight: 217.09
• Product Categories: Heterocycles;Thiophene&Benzothiophene;Thiophene intermediates;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiophenes;ThiophenesBuilding Blocks;Building Blocks;C4 to C6;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocycle-oher series
• Mol File: 2766-74-7.mol

Chemical Properties

• Melting Point: 25-28°C
• Boiling Point: 112-117 °C(lit.)
• Flash Point: >230 °F
• Appearance: /solid
• Density: 1.623 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.586(lit.)
• Storage Temp.: Keep Cold
• Water Solubility: Not miscible in water.
• Sensitive: Moisture Sensitive
• BRN: 130710
• CAS DataBase Reference: 5-Chlorothiophene-2-sulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chlorothiophene-2-sulfonyl chloride(2766-74-7)
• EPA Substance Registry System: 5-Chlorothiophene-2-sulfonyl chloride(2766-74-7)

Safety Data

• Hazard Codes: C
• Statements: 34-29-14
• Safety Statements: 26-27-36/37/39-45-28A-25
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2766-74-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Chlorothiophene-2-sulfonyl chloride is used as a key intermediate for the preparation of Notch-1-sparing γ-secretase inhibitors, which are crucial in the treatment of Alzheimer's disease. These inhibitors help modulate the Notch signaling pathway, which plays a significant role in the progression of the disease.
Used in Organic Synthesis:
5-Chlorothiophene-2-sulfonyl chloride serves as an important raw material and intermediate in organic synthesis, where it is utilized to create a variety of complex organic compounds.
Used in Agrochemicals Industry:
In the agrochemicals industry, 5-Chlorothiophene-2-sulfonyl chloride is employed as a vital intermediate for the synthesis of various agrochemical products, contributing to the development of effective pest control solutions.
Used in Dyestuffs Industry:
5-Chlorothiophene-2-sulfonyl chloride is also used in the dyestuffs industry as a key component in the production of different types of dyes, enhancing the colorfastness and performance of the final products.

Synthesis Reference(s)

Tetrahedron, 21, p. 1333, 1965 DOI: 10.1016/S0040-4020(01)98293-6

InChI:InChI=1/C4H2Cl2O2S2/c5-3-1-2-4(9-3)10(6,7)8/h1-2H

Upstream product

• 96-43-5 2-thienyl chloride 

Downstream Products

• 55854-42-7 N-phenyl-5-chloro-2-thiophenesulfonyl amide 
• 58457-24-2 5-chloro-4-nitro-2-thiophenesulfonyl chloride 
• 155731-14-9 N-(tert-butyl)-5-chloro-2-thiophenesulfonamide 
• 78380-28-6 5-chloro-2-thiophenesulfonyl hidrazide 
• 53595-66-7 2-chlorothiophene-5-sulfonamide 

Relevant articles and documents

[4-(6-FLUORO-7-METHYLAMINO-2,4-DIOXO-1,4-DIHYDRO-2H-QUINAZOLIN-3-YL)-PHENYL]-5-CHLORO-THIOPHEN-2-YL-SULFONYLUREA SALTS, FORMS AND METHODS RELATED THERETO

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SUBSTITUTED-(QUINAZOLINYL)PHENYL THIOPHENYL-SULFONYLUREAS, METHODS FOR MAKING AND INTERMEDIATES THEREOF

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2,3-Dihydro-3-oxo-thienoisothiazol-1,1-dioxides and their 3-thioxo compounds

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STUDIES IN THE HETEROCYCLIC COMPOUNDS V. SOME REACTIONS OF 5-CHLORO-2-THIOPHENESULFONYL DERIVATIVES

The reactions of 5-chloro-2-thiophenesulfonyl chloride are described.Treatment of the sulfonyl chloride with ammonia, hydrazine hydrate, sodium azide, indole and imidazole gave the sulfonamides (5), sulfonohydrazide (4), sulfonyl azide (3), 1-(5-chloro-2-thiophenesulfonyl)indole (27) and 1-(5-chloro-2-thiophenesulfonyl)-imidazole (26), respectively.The sulfonyl chloride was reacted further with 20 aryl and cycloalkyl-amines to give the corresponding sulfonamides (6)-(25).Attempted chlorination of the sulfonyl chloride (2) with sulfuryl chloride or bromination of the sulfonyl azide (3) with pyridinium bromide perbromide failed.However, nitration of the sulfonyl chloride (2) with fuming nitric acid gave the 4-nitro-sulfonyl chloride (28), which with sodium azide afforded the 5-chloro-4-nitro-sulfonyl azide (29).The sulfonyl azides, (3) and (29), have been reacted with triphenylphosphine, triethylphosphite, norbornene and cyclohexene.The azides reacted further with indole and 1-methylindole to give the 2-sulfonyliminoindoles (34)-(36).The infrared spectra and mass spectra of some of the substituted thiophenesulfonyl derivatives are discussed.

Fungicidal 5-dialkylamino-4-nitrosulfonamidothiophenes

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