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

General 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 is widely used as a synthetic intermediate in the production of pharmaceuticals, dyes, and agrochemicals. 4-chlorobenzenesulfonyl fluoride is a versatile reagent in organic chemistry, particularly in the synthesis of sulfonamides. It is also used as a reagent in the synthesis of various pharmacological and biological compounds due to its ability to introduce the sulfonyl fluoride moiety into organic molecules. Additionally, it is used as a fluorinating agent in organic synthesis and has applications in the production of specialty resins and polymers. However, it is important to handle this compound with caution as it is corrosive and can cause irritation to the skin, eyes, and respiratory system.

Upstream product

• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 98-64-6 4-Chlorobenzenesulfonamide 
• 637-87-6 1-Chloro-4-iodobenzene 
• 106-54-7 p-Chlorothiophenol 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 98-66-8 4-chloro-benzenesulfonic acid 
• 14204-31-0 2-(4-chlorophenylthio)isoindoline-1,3-dione 
• 1679-18-1 4-Chlorophenylboronic acid 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 106-39-8 bromochlorobenzene 
• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 1146-44-7 4,4'-dichlorophenyl thiosulfonate 
• 2725-55-5 di(4-chlorobenzenesulfonyl)amine 

Downstream Products

• 101079-89-4 4-chloro-benzenesulfonic acid-(2-chloro-ethyl ester) 
• 497959-21-4 1-(4-Chloro-benzenesulfonyl)-2-(4-thiomorpholin-4-ylmethyl-phenyl)-1,2,3,4-tetrahydro-quinoline 
• 383-11-9 4-(trifluoromethylsulfonyl)chlorobenzene 
• 2051-62-9 4'-biphenyl chloride 
• 1254832-42-2 1-chloro-4-(fluoro(phenylsulfonyl)methylsulfonyl)benzene 
• 13656-61-6 2-methylphenyl phenyl p-fluorobenzenesulfonate 
• 402-46-0 4-fluorophenylsulphonamide 
• 312-52-7 N-phenyl-S-(4-fluorophenyl) sulfonamide 
• 349-88-2 4-Fluorobenzenesulfonyl chloride 
• 97-09-6 4-Chloro-3-nitrobenzenesulfonamide 
• 100709-81-7 4-chloro-benzolsulfynoic acid ; S-benzyl-thiuronium-salt 
• 447460-28-8 N-(1-{4-[2-(4-chloro-benzenesulfonyl)-4-methoxy-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 
• 864872-87-7 N-(1-{4-[2-(4-chloro-benzenesulfonyl)-4-trifluoromethyl-benzenesulfonyl]-phenyl}-ethyl)-2,2,2-trifluoro-acetamide 

Relevant articles and documents

Fluorination method

In order to overcome the problems of high cost and low stability of the existing fluorination reagents for preparing acyl fluoride, sulfonyl fluoride and phosphoryl fluoride compounds, the invention provides a fluorination method, which comprises the following operation steps of: adding a fluorination reagent into a substrate, wherein the fluorination reagent comprises cations M and anions, the anions are selected from one or more of perfluoropolyether chain carboxylic acid anions as shown in the specification: CF3(OCF2)nCO2, wherein n is selected from 1-10; the substrate comprises a carboxylic acid compound, a sulfonic acid compound, a phosphoric acid compound and a phosphine oxide compound; and carrying out fluorination reaction to obtain acyl fluoride, sulfonyl fluoride and phosphoryl fluoride products. According to the fluorination method provided by the invention, the perfluoropolyether chain carboxylate is used as a fluorination reagent, so that the dehydroxylation fluorination reaction of the carboxylic acid compound, the sulfonic acid compound and the phosphoric acid compound and the fluorination reaction of the phosphine oxide compound are realized, the product yield isrelatively high, and the fluorination method has relatively good universality for different substrates.

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.