349-89-3

Basic information

• Product Name: 4-chlorobenzenesulfonyl fluoride
• Synonyms: 4-Chlorobenzenesulfonyl fluoride; benzenesulfonyl fluoride, 4-chloro-
• CAS NO: 349-89-3
• Molecular Formula: C₆H₄ClFO₂S
• Molecular Weight: 194.6112
• Mol File: 349-89-3.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 236.3°C at 760 mmHg
• Flash Point: 96.7°C
• Density: 1.473g/cm³
• Vapor Pressure: 0.0733mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: 4-chlorobenzenesulfonyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chlorobenzenesulfonyl fluoride(349-89-3)
• EPA Substance Registry System: 4-chlorobenzenesulfonyl fluoride(349-89-3)

Safety Data

• Hazardous Substances Data: 349-89-3(Hazardous Substances Data)

Usage

Description

4-Chlorobenzenesulfonyl fluoride, also known as Sulfuryl fluoride or Sulfuryl chloride fluoride, is a chemical compound with the formula C6H4ClFO2S. It is a colorless liquid that serves as a synthetic intermediate in the production of pharmaceuticals, dyes, and agrochemicals. This versatile reagent in organic chemistry is particularly useful in the synthesis of sulfonamides and is valued for its ability to introduce the sulfonyl fluoride moiety into organic molecules. It also functions as a fluorinating agent in organic synthesis and finds applications in the production of specialty resins and polymers. However, due to its corrosive nature and potential to cause irritation to the skin, eyes, and respiratory system, careful handling is required.

Uses

Used in Pharmaceutical Industry:
4-Chlorobenzenesulfonyl fluoride is used as a synthetic intermediate for the production of various pharmaceuticals. Its ability to introduce the sulfonyl fluoride moiety into organic molecules makes it a valuable component in the synthesis of a range of medicinal compounds.
Used in Dye Industry:
In the dye industry, 4-chlorobenzenesulfonyl fluoride is utilized as a synthetic intermediate, contributing to the development of new dye products.
Used in Agrochemical Industry:
4-chlorobenzenesulfonyl fluoride is also employed as a synthetic intermediate in the agrochemical sector, playing a role in the creation of various agrochemical products.
Used in Organic Chemistry as a Reagent:
4-Chlorobenzenesulfonyl fluoride is used as a reagent in the synthesis of sulfonamides, which are an important class of compounds with applications as antimicrobial agents.
Used as a Fluorinating Agent:
In organic synthesis, 4-chlorobenzenesulfonyl fluoride serves as a fluorinating agent, facilitating the incorporation of fluorine into organic molecules, which can enhance their reactivity or stability.
Used in Specialty Resins and Polymers Production:
4-chlorobenzenesulfonyl fluoride has applications in the production of specialty resins and polymers, where it may contribute to the development of materials with unique properties.

Upstream product

• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 108-90-7 chlorobenzene 
• 98-64-6 4-Chlorobenzenesulfonamide 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 2725-55-5 di(4-chlorobenzenesulfonyl)amine 
• 1146-44-7 4,4'-dichlorophenyl thiosulfonate 
• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 106-39-8 bromochlorobenzene 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 637-87-6 1-Chloro-4-iodobenzene 
• 106-54-7 p-Chlorothiophenol 
• 1679-18-1 4-Chlorophenylboronic acid 
• 14204-31-0 2-(4-chlorophenylthio)isoindoline-1,3-dione 
• 98-66-8 4-chloro-benzenesulfonic acid 

Downstream Products

• 100-03-8 4-chlorobenzenesulfinic acid 
• 349-04-2 4-chloro-3-nitrobenzenesulfonyl fluoride 
• 6621-62-1 4-chloro-benzenesulfonic acid-(2,4-dichloro-phenyl ester) 
• 101079-89-4 4-chloro-benzenesulfonic acid-(2-chloro-ethyl ester) 
• 383-11-9 4-(trifluoromethylsulfonyl)chlorobenzene 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 368-85-4 4-fluorobenzenesulfonyl fluoride 
• 864872-88-8 N-(1-{4-[2-(4-chloro-benzenesulfonyl)-benzenesulfonyl]-phenyl}-ethyl)-2,2,2-trifluoro-acetamide 
• 864872-97-9 N-(1-{4-[4-chloro-2-(4-chloro-benzenesulfonyl)-benzenesulfonyl]-phenyl}-ethyl)-2,2,2-trifluoro-acetamide 
• 864872-87-7 N-(1-{4-[2-(4-chloro-benzenesulfonyl)-4-trifluoromethyl-benzenesulfonyl]-phenyl}-ethyl)-2,2,2-trifluoro-acetamide 
• 864872-86-6 N-(1-{4-[2-(4-chloro-benzenesulfonyl)-4-cyclopentyloxy-benzenesulfonyl]-phenyl}-ethyl)-2,2,2-trifluoro-acetamide 
• 447460-28-8 N-(1-{4-[2-(4-chloro-benzenesulfonyl)-4-methoxy-benzenesulfonyl]-phenyl}-ethyl)-2,2,2-trifluoro-acetamide 
• 100709-81-7 4-chloro-benzolsulfynoic acid ; S-benzyl-thiuronium-salt 
• 97-09-6 4-Chloro-3-nitrobenzenesulfonamide 

Relevant articles and documents

Metal-Free Visible-Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism

The first metal-free procedure for the synthesis of arylsulfonyl fluorides is reported. Under organo-photoredox conditions, aryl diazonium salts react with a readily available SO2 source (DABSO) to afford the desired product through simple nucleophilic fluorination. The reaction tolerates the presence of both electron-rich and -poor aryls and demonstrated a broad functional group tolerance. To shed the light on the reaction mechanism, several experimental techniques were combined, including fluorescence, NMR, and EPR spectroscopy as well as DFT calculations.

Copper-catalyzed three-component reaction of arylhydrazine hydrochloride, DABSO, and NFSI for the synthesis of arenesulfonyl fluorides

This paper reports a convenient copper-catalyzed three-component conversion of arylhydrazine hydrochlorides to arenesulfonyl fluorides in good yields under mild conditions, using 1,4-diazabicyclo [2.2.2]octane bis(sulfur dioxide) (DABSO) as a sulfonyl source andN-fluorobenzenesulfonimide (NFSI) as a fluorine source based on a radical sulfur dioxide insertion and fluorination strategy. Notably, arylhydrazine hydrochloride is used as a safe precursor of aryl radicals.