335-05-7

Basic information

• Product Name: TRIFLUOROMETHANESULFONYL FLUORIDE
• Synonyms: PFC-MSF;methanesulfonylfluoride,trifluoro-;trifluoro-methanesulfonylfluorid;trifluoromethylsulfonylfluoride;TRIFLUOROMETHANESULPHONYL FLUORIDE;TRIFLUOROMETHANESULFONYL FLUORIDE;Trifluorometansulfonyl fluoride;Trifluoromethanesulphonyl fluoride 99%
• CAS NO: 335-05-7
• Molecular Formula: CF4O2S
• Molecular Weight: 152.07
• EINECS: 206-384-8
• Mol File: 335-05-7.mol
• Article Data: 25

Chemical Properties

• Boiling Point: -25°C
• Flash Point: -59.238 °C
• Appearance: /
• Density: 1.73 g/cm³
• Vapor Pressure: 0.146mmHg at 25°C
• Refractive Index: 1.359
• CAS DataBase Reference: TRIFLUOROMETHANESULFONYL FLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIFLUOROMETHANESULFONYL FLUORIDE(335-05-7)
• EPA Substance Registry System: TRIFLUOROMETHANESULFONYL FLUORIDE(335-05-7)

Safety Data

• Hazard Codes: T
• Statements: 20-34
• Safety Statements: 26-36/37/39
• RIDADR: 3308
• TSCA: T
• HazardClass: GAS, TOXIC
• Hazardous Substances Data: 335-05-7(Hazardous Substances Data)

Usage

General Description

Trifluoromethanesulfonyl Fluoride, also known as Triflic Fluoride or TFMSF, is a chemical compound with the molecular formula CF3SO2F. It is a colorless, pungent liquid, and it is highly reactive and corrosive. The chemical is often used as a source of fluorine in organic synthesis, and in the manufacture of other chemicals as it can act as a catalyst for certain types of reactions. Like many fluorine compounds, it can be dangerous and it requires safe handling because of its reactivity and corrosivity.

InChI:InChI=1/C4H4F3NO/c1-3(9,2-8)4(5,6)7/h9H,1H3

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 3518-65-8 monochloromethanesulfonyl chloride 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 110073-91-1 propane-1,3-disulfonyl difluoride 
• 558-25-8 methyl fluorosulfonate 
• 478945-43-6 C₃H₉F₂Si^(1-)*C₇H₁₈N₃⁽¹⁺⁾ 
• 3582-05-6 trifluoromethyl trifluoromethanesulfonate 
• 479024-67-4 2-dimethylamino-1,3-dimethylimidazolinium difluorotrimethylsilicate 
• 373-68-2 tetramethylammonium fluoride 
• 150746-76-2 tris(dimethylamino)sulfonium trimethylsilyldifluoride 
• 23588-89-8 triethylamine hydrofluoride 
• 220405-40-3 2,2-difluoro-1,3-dimethyl-imidazolidine 
• 1493-13-6 trifluorormethanesulfonic acid 
• 7789-21-1 fluorosulphonic acid 

Downstream Products

• 6401-00-9 2,2,3,3,3-pentafluoropropyl triflate 
• 29540-84-9 4-chlorophenyl trifluoromethanesulfonate 
• 17763-67-6 Phenyl triflate 
• 32578-28-2 (3-Aminophenyl)-trifluormethansulfonat 
• 17763-70-1 methyl 2-(trifluoromethylsulfonyloxy)benzoate 
• 41605-69-0 2,4-dichlorophenyl trifluoromethanesulfonate 
• 428-76-2 bis(trifluoromethanesulfonyl)methane 
• 34310-29-7 N-methyltrifluoromethanesulfonamide 
• 91742-21-1 sodium bis(trifluoromethanesulfonyl)imide 
• 169394-00-7 (+/-)-S-methyl-S-phenyl-N-(trifluoromethylsulfonyl)sulfoximine 
• 353-50-4 Carbonyl fluoride 
• 15719-64-9 methylammonium carbonate 
• 90076-65-6 bis(trifluoromethane)sulfonimide lithium 
• 314756-98-4 2-(methacryloyloxy)ethyltrifluoromethanesulfonamide 

Relevant articles and documents

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Trifluoromethyl Triflate: Synthesis and Reactions

A new and convenient synthesis of trifluoromethyl trifluoromethanesulfonate (trifluoromethyl triflate, TFMT) has been devised.The addition of triflic anhydride to a catalytic amount of antimony pentafluoride at 25 deg C produces TFMT in 94percent yield, utilizing a new and stronger Lewis acid catalyst produced in the reaction, F4SbOSO2CF3.This reaction makes pure TFMT conveniently and economically available in large quantities.A mechanism is presented that accounts for the substitution of a triflate ligand on antimony, as well as for the formation of TFMT.Trifluoromethyltriflate does not trifluoromethylate nucleophiles (pyridine, triethylamine, iodide, phenyllithium, phenylmagnesium bromide, lithium thiophenolate, or sodium naphthalenide) but gives products that result from an initial attack of the nucleophile at sulfur.Fluoride ion, which is formed by fragmentation of the trifluoromethoxide ion displaced from sulfur, is a chain carrier in the rapid decomposition of TFMT to give trifluoromethanesulfonyl fluoride and fluorophosgene.This limits the synthetic utility of trifluoromethyl triflate.

SYNTHESIS OF PERFLUOROPROPANE-1,3-DISULFONIC ACID AND PERFLUOROBUTANE-1,4-DISULFONIC ACID

Perfluoropropane-1,3-disulfonic acid, HO3S-(CF2)3-SO3H, and perfluorobutane-1,4-disulfonic acid, HO3S-(CF2)4-SO3H, have been prepared electrochemically from the alkanedisulfonyl difluorides.Whereas perfluoroalkanemonosulfonyl fluorides can easily be prepared via electrochemical fluorination the situation with disulfonyl difluorides is somewhat more difficult.NMR data are reported for all compounds.

PRODUCTION METHOD OF AMMONIUM PERFLUOROALKANE SULFONAMIDE

PROBLEM TO BE SOLVED: To provide a production method of ammonium perfluoroalkane sulfonamide, which has high generation rate and high utilization efficiency of raw materials. SOLUTION: A production method of ammonium perfluoroalkane sulfonamide is selected which includes: an electrolytic fluorination step to obtain a product gas including perfluoroalkanesulfonyl fluoride by electrolytic fluorination of an alkane sulfonyl halide or tetrahydrothiophene-1,1-dioxide in anhydrous hydrogen fluoride; and a product gas reaction step to bring the product gas into contact with ammonia water and obtain a reaction liquid, in which the produced ammonium perfluoroalkane sulfonamide is dissolved and exists in the ammonia water, in which the electrolytic fluorination step and the product gas reaction step are conducted continuously, and simultaneously the amount of ammonia in the reaction liquid is maintained in a range of 3-12 pts.mass based on 100 pts.mass of the reaction liquid. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

PROCESS FOR FLUORINATION OF SULPHONYL HALIDE COMPOUNDS

The present disclosure relates to the preparation of a compound of formula (I) comprising an —SO2F function, R—SO2F, by reacting a compound of formula (II), R′—SO2X, with a fluorinating agent, the process carried out in the liquid phase in the presence of hydrofluoric acid using an antimony-based fluorination catalyst, wherein R, R′, and X are described herein.