33719-37-8

Basic information

• Product Name: Benzenesulfonyl fluoride, 4-cyano-
• CAS NO: 33719-37-8
• Molecular Formula: C7H4FNO2S
• Molecular Weight: 185.179
• Mol File: 33719-37-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzenesulfonyl fluoride, 4-cyano-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonyl fluoride, 4-cyano-(33719-37-8)
• EPA Substance Registry System: Benzenesulfonyl fluoride, 4-cyano-(33719-37-8)

Safety Data

• Hazardous Substances Data: 33719-37-8(Hazardous Substances Data)

Upstream product

• 2863-98-1 4-hydrazinobenzonitrile hydrochloride 
• 2252-32-6 4-cyanophenyldiazonium tetrafluoroborate 
• 49584-26-1 p-cyanobenzenesulfonyl chloride 
• 3058-39-7 4-iodobenzonitrile 

Downstream Products

• 58743-77-4 4'-methoxybiphenyl-4-carbonitrile 
• 56768-46-8 4-cyano-N-phenyl-benzenesulfonamide 
• 10540-31-5 4-cyano-4'-fluorobiphenyl 
• 113547-30-1 2’-methoxy-[1,1’-biphenyl]-4-carbonitrile 
• 189828-30-6 4-cyano-2'-methyl-1,1'-biphenyl 
• 50670-50-3 p-(p-tolyl)benzonitrile 
• 1026020-39-2 4-cyanobenzenesulfonyl azide 

Relevant articles and documents

Visible-Light-Mediated Synthesis of Sulfonyl Fluorides from Arylazo Sulfones

Sulfonyl fluorides are useful motifs for a wide range of applications in organic synthesis including sulfur (VI) fluoride exchange-based “click chemistry.” Herein, a visible-light-mediated synthesis of sulfonyl fluorides from arylazo sulfones is described. In the present study, K2S2O5 and N-fluorobenzenesulfonimide (NFSI) were used as the sulfonyl source and fluorinating agent, respectively, for visible-light-mediated fluorosulfonylation of arylazo sulfones to prepare various sulfonyl fluorides in 60–85% yield. This protocol is a synthetic approach to provide useful sulfonyl fluoride structures at room temperature. (Figure presented.).

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.

Arenesulfonyl Fluoride Synthesis via Copper-free Sandmeyer-type Fluorosulfonylation of Arenediazonium Salts

The limited availability of highly valuable arenesulfonyl fluorides seriously hinders their further application in many research fields including medicinal chemistry and chemical biological, organic synthesis, polymer preparation, etc. We report herein a mild and efficient copper-free Sandmeyer-type fluorosulfonylation reaction of various arenediazonium salts to prepare valuable arenesulfonyl fluorides using K2S2O5 as both a reductant and a practical sulfonyl source in combination with N-fluorobenzenesulfonimide as an effective fluorine source. This methodology provides an attractive route to diverse important arenesulfonyl fluorides given the overall practicality and scope.