53595-66-7

Basic information

• Product Name: 5-Chlorothiophene-2-sulfonamide
• Synonyms: 2-Chloro-5-sulfamoylthiophene;TIMTEC-BB SBB003565;5-chloro-2-thiophenesulfonamid;5-chloro-2-thiophenesulfonamide;2-CHLORO THIOPHENE-5-SULFONAMIDE;5-CHLOROTHIOPHENE-2-SULFONAMIDE;5-CHLOROTHIOPHENE-2-SULPHONAMIDE;BUTTPARK 27\04-10
• CAS NO: 53595-66-7
• Molecular Formula: C₄H₄ClNO₂S₂
• Molecular Weight: 197.66
• Product Categories: Heterocycle-oher series;SULFONAMIDE;Thiophene&Benzothiophene;Thiophene intermediates;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiophenes;ThiophenesBuilding Blocks
• Mol File: 53595-66-7.mol

Chemical Properties

• Melting Point: 113-117 °C(lit.)
• Boiling Point: 366.3 °C at 760 mmHg
• Flash Point: 175.3 °C
• Appearance: White to light yellow crystal powder
• Density: 1.649 g/cm³
• Vapor Pressure: 1.48E-05mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: soluble in Methanol
• PKA: 9.75±0.60(Predicted)
• CAS DataBase Reference: 5-Chlorothiophene-2-sulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chlorothiophene-2-sulfonamide(53595-66-7)
• EPA Substance Registry System: 5-Chlorothiophene-2-sulfonamide(53595-66-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-45-37/39
• WGK Germany: 3
• RTECS: XN0296000
• HazardClass: IRRITANT
• Hazardous Substances Data: 53595-66-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
5-Chlorothiophene-2-sulfonamide is used as a synthetic intermediate for the creation of non-benzofused bicyclo[4.2.1]nonanes. Its unique chemical properties make it a valuable component in the synthesis of various complex organic compounds, contributing to the development of novel materials and pharmaceuticals.
Used in Pharmaceutical Industry:
Within the pharmaceutical industry, 5-Chlorothiophene-2-sulfonamide serves as a key building block for the development of new drugs. Its ability to undergo N-alkylation reactions allows for the creation of diverse molecular structures with potential therapeutic applications.
Used in Research and Development:
In the field of research and development, 5-Chlorothiophene-2-sulfonamide is utilized as a starting material for exploring new chemical reactions and understanding the underlying mechanisms. This contributes to the advancement of chemical knowledge and the potential discovery of new compounds with various applications.
Used in Material Science:
5-Chlorothiophene-2-sulfonamide may also find applications in material science, where its unique chemical properties can be exploited to develop new materials with specific characteristics, such as improved stability or enhanced reactivity.

InChI:InChI=1/C4H4ClNO2S2/c5-3-1-2-4(9-3)10(6,7)8/h1-2H,(H2,6,7,8)

Upstream product

• 2766-74-7 5-chlorothien-2-ylsulfonyl chloride 
• 3172-52-9 2,5-diclorothiophene 
• 16629-19-9 thiophene-2-sulfonyl chloride 
• 155731-14-9 N-(tert-butyl)-5-chloro-2-thiophenesulfonamide 

Downstream Products

• 438208-72-1 5-chloro-2-{4-[({[(5-chloro(2-thienyl))sulfonyl]amino}thioxomethyl)amino]-2-methylphenyl}benzo[c]azolidine-1,3-dione 
• 438209-71-3 N-[4-(2,4-dioxo(1,3-dihydroquinazolin-3-yl))-3-bromophenyl]{[(5-chloro(2-thienyl))sulfonyl]amino}carboxamide 
• 438210-16-3 N-{4-[(tert-butoxy)carbonylamino]-3-methylphenyl}{[(5-chloro(2-thienyl))sulfonyl]amino}carboxamide 
• 438209-04-2 N-[4-({[(5-chloro(2-thienyl))sulfonyl]amino}carbonylamino)-2-methylphenyl]benzamide 
• 55854-42-7 N-phenyl-5-chloro-2-thiophenesulfonyl amide 
• 1427214-90-1 C₂₂H₁₆Cl₂N₂O₅S₂ 
• 1427215-11-9 C₂₄H₂₀Cl₂N₂O₅S₂ 
• 1225035-41-5 C₇H₁₀N₂*C₁₁H₈ClNO₄S₂ 
• 1225035-40-4 C₁₁H₈ClNO₄S₂ 
• 1138722-50-5 C₂₃H₂₁Cl₃N₂O₄S₂ 
• 849792-53-6 1-(4-(7-(4-fluorobenzylamino)-2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl)-2,6-dimethylphenyl)-3-(5-chlorothiophen-2-ylsulfonyl)urea 

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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.