52201-01-1

Basic information

• Product Name: 4-(trifluoromethyl)benzene-1-sulfonyl fluoride
• Synonyms: 4-(trifluoromethyl)benzene-1-sulfonyl fluoride
• CAS NO: 52201-01-1
• Molecular Weight: 228.167
• Mol File: 52201-01-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 4-(trifluoromethyl)benzene-1-sulfonyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(trifluoromethyl)benzene-1-sulfonyl fluoride(52201-01-1)
• EPA Substance Registry System: 4-(trifluoromethyl)benzene-1-sulfonyl fluoride(52201-01-1)

Safety Data

• Hazardous Substances Data: 52201-01-1(Hazardous Substances Data)

Upstream product

• 2991-42-6 4-trifluorophenylsulfonyl chloride 
• 825-83-2 4-trifluoromethylbenzenethiol 
• 830-43-3 4-(trifluoromethyl)benzenesulfonamide 

Downstream Products

• 163105-69-9 5-(4-(trifluoromethyl)phenyl)-1H-indole 
• 127783-73-7 methyl 4’-(trifluoromethyl)-[1,1’-biphenyl]-4-carboxylate 
• 1262727-73-0 ethyl 4-(trifluoromethyl)benzenesulfonate 
• 1286023-30-0 phenyl 4-trifluoromethylbenzenesulfonate 
• 21718-11-6 N-phenyl-S-(4-trifluoromethylphenyl) sulfonamide 
• 1152979-96-8 4-(trifluoromethyl)benzenesulfonyl azide 
• 864872-81-1 2,2,2-trifluoro-N-{1-[4-(4-trifluoromethyl-benzenesulfonyl)-phenyl]-ethyl}-acetamide 

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.

A Unified Strategy for Arylsulfur(VI) Fluorides from Aryl Halides: Access to Ar-SOF3 Compounds

A convenient protocol to selectively access various arylsulfur(VI) fluorides from commercially available aryl halides in a divergent fashion is presented. Firstly, a novel sulfenylation reaction with the electrophilic N-(chlorothio)phthalimide (Cl-S-Phth) and arylzinc reagents afforded the corresponding Ar-S-Phth compounds. Subsequently, the S(II) atom was selectively oxidized to distinct fluorinated sulfur(VI) compounds under mild conditions. Slight modifications on the oxidation protocol permit the chemoselective installation of 1, 3, or 4 fluorine atoms at the S(VI) center, affording the corresponding Ar-SO2F, Ar-SOF3, and Ar-SF4Cl. Of notice, this strategy enables the effective introduction of the rare and underexplored -SOF3 moiety into various (hetero)aryl groups. Reactivity studies demonstrate that such elusive Ar-SOF3 can be utilized as a linchpin for the synthesis of highly coveted aryl sulfonimidoyl fluorides (Ar-SO(NR)F).

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.