498-83-9

Basic information

• Product Name: 4-BroMobenzenesulfonyl fluoride
• Synonyms: 4-BroMobenzenesulfonyl fluoride;AOXWZFUBFROIHA-UHFFFAOYSA-N
• CAS NO: 498-83-9
• Molecular Formula: C₆H₄BrFO₂S
• Molecular Weight: 239.0621632
• Mol File: 498-83-9.mol
• Article Data: 19

Chemical Properties

• Melting Point: 60-65°C
• Boiling Point: 256.0±23.0 °C(Predicted)
• Appearance: /
• Density: 1.753±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4-BroMobenzenesulfonyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BroMobenzenesulfonyl fluoride(498-83-9)
• EPA Substance Registry System: 4-BroMobenzenesulfonyl fluoride(498-83-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8 / PGII
• WGK Germany: 3
• Hazardous Substances Data: 498-83-9(Hazardous Substances Data)

Upstream product

• 14204-32-1 N-((4-bromophenol)thio)phthalimide 
• 3376-24-7 N-tert-butyl-α-phenylnitrone 
• 622-88-8 4-bromophenylhydrazine hydrochloride 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 701-34-8 4-bromo-benzenesulfonic acid amide 
• 106-53-6 para-bromobenzenethiol 
• 5467-74-3 4-Bromophenylboronic acid 
• 848649-38-7 4-bromobenzenesulfonic acid pentafluorophenyl ester 
• 1156-18-9 di(4-bromobenzenesulfonyl)amine 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 34176-08-4 sodium 4-bromobenzenesulfinate 
• 108-86-1 bromobenzene 

Downstream Products

• 435309-95-8 N-(BOC)-(D,L)-3-(4'-bromophenyl)sulfonyl-nipecotic acid, ethyl ester 
• 312-20-9 1-bromo-4-(trifluoromethylsulfonyl)benzene 
• 16236-44-5 2-Methoxy-1,1′:4′,1′′-terphenyl 
• 6647-76-3 p-bromobenzenesulfonyl azide 

Relevant articles and documents

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.

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.

Synthesis of Sulfonyl Fluorides from Sulfonamides

A simple and practical synthesis of sulfonyl fluorides from sulfonamides is reported. The method capitalizes on the formation of the sulfonyl chloride by virtue of the reaction of Pyry-BF4 and MgCl2, and subsequent in situ conversion to the more robust and stable sulfonyl fluoride by the presence of KF. The mild conditions and high chemoselectivity of the protocol enable the late-stage formation of sulfonyl fluorides from densely functionalized molecules.