335-05-7

Usage

Uses

Used in Organic Synthesis:
TRIFLUOROMETHANESULFONYL FLUORIDE is used as a fluorine source for [reactions involving the introduction of fluorine atoms into organic molecules] because of its high reactivity and ability to facilitate fluorination reactions.
Used in Chemical Manufacturing:
TRIFLUOROMETHANESULFONYL FLUORIDE is used as a catalyst in [certain types of chemical reactions] for [enhancing reaction rates and improving the yield of desired products], given its capacity to act as a catalyst in specific processes.
Used in Pharmaceutical Industry:
TRIFLUOROMETHANESULFONYL FLUORIDE is used as a reagent in [the synthesis of pharmaceutical compounds] for [its role in the formation of complex molecules with potential therapeutic applications], highlighting its utility in creating new drug candidates.
Used in Material Science:
TRIFLUOROMETHANESULFONYL FLUORIDE is used as a component in [the development of advanced materials] for [its contribution to the properties of materials such as polymers and coatings], showcasing its versatility in material synthesis.

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

Upstream product

• 558-25-8 methyl fluorosulfonate 
• 124-63-0 methanesulfonyl chloride 
• 110-86-1 pyridine 
• 3582-05-6 trifluoromethyl trifluoromethanesulfonate 
• 3518-65-8 monochloromethanesulfonyl chloride 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 60669-28-5 Trifluoromethyliodine(III) bis-trifluoroacetate 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 677-67-8 fluorosulfonyldifluoroacetyl fluoride 
• 3518-66-9 1-chloro-ethanesulfonyl chloride 
• 478945-43-6 C₃H₉F₂Si^(1-)*C₇H₁₈N₃⁽¹⁺⁾ 
• 479024-67-4 2-dimethylamino-1,3-dimethylimidazolinium difluorotrimethylsilicate 
• 373-68-2 tetramethylammonium fluoride 
• 150746-76-2 tris(dimethylamino)sulfonium trimethylsilyldifluoride 

Downstream Products

• 428-76-2 bis(trifluoromethanesulfonyl)methane 
• 1493-13-6 trifluorormethanesulfonic acid 
• 456-64-4 phenyl trifluoromethanesulfonamide 
• 6401-02-1 2,2,3,3-tetrafluoropropyl trifluoromethanesulfonate 
• 6401-00-9 2,2,3,3,3-pentafluoropropyl triflate 
• 6401-01-0 2,2,3,3,4,4,4-heptafluorobutyl trifluoromethanesulfonate 
• 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 
• 28048-17-1 N,N-dimethyl-trifluoromethanesulfonamide 
• 40906-82-9 bis(trifluoromethylsulfonyl)phenylmethane 
• 91742-21-1 sodium bis(trifluoromethanesulfonyl)imide 

Relevant academic research and scientific papers

The protonation of CF3SO3H: Preparation and characterization of trifluoromethyldihydroxyoxosulfonium hexafluoridoantimonate, CF3SO3H2+SbF6 -

Trifluoromethanesulfonic anhydride reacts with superacidic solutions AF/SbF5 (A = H, D) to form their corresponding salts CF 3SO3A2+SbF6-, which are protonated forms of trifluoromethanesulfonic acid and CF 3SO2F as by-product. The salts have been characterized by vibrational spectroscopy and single-crystal structural analysis. CF 3SO3H2+SbF6- crystallizes in the triclinic space group Pβar {1}$ with two formula units in the unit cell: a = 709.29(5) pm, b = 763.46(5) pm, c = 882.15(6) pm; α = 71.884(6)°, β = 72.488(6)°, γ = 84.509(6)°; V = 432.97(5) A3. The cations are linked with two strong hydrogen bonds to SbF6- anions to form chains. The experimental data were also compared to quantum chemical calculations for the CF3SO3H2(HF)2+ cation.

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.

Perfluoroethanesulfonyl fluoride: Preparation from sultone

A procedure was developed for preparing perfluoroethanesulfonyl fluoride by synthesis of hexafluoropropane-2-β-sultone from sulfuric anhydride and perfluoropropene, followed by hydrolysis of the sultone to α- tetrafluoroethanesulfonyl fluoride and fluorination of the latter with elemental fluorine.

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.

Process for fluorinating inorganic or organic compounds by direct fluorination

The invention relates to the use of a fluorinated gas, wherein the elemental fluorine (F2) is present at a high concentration, the present invention relates to a process for producing fluorinated compounds by direct fluorination using a fluorination gas in which elemental fluorine (F2) is present at a high concentration, such as a concentration of elemental fluorine (F2), in particular equal to much higher than 15 vol% or even 20 vol% (i.e., at least 15 vol% or even 20 vol%), and to a process for producing fluorinated compounds by direct fluorination using a fluorination gas. The process of the present invention relates to the manufacture of fluorinated compounds other than fluorinated benzene by direct fluorination, in particular to the preparation of fluorinated organic compounds, end products and intermediates for use in agricultural, pharmaceutical, electronic, catalyst, solvent and other functional chemical applications. The fluorination process of the invention can be carried outin batches or in a continuous manner. If the process of the invention is carried out in batches, a column (tower) reactor may be used. If the process of the invention is continuous, a microreactor may be used.

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

Trifluoromethylfluorosulfonylation of Unactivated Alkenes Using Readily Available Ag(O2CCF2SO2F) and N-Fluorobenzenesulfonimide

Presented is a novel intermolecular radical trifluoromethylfluorosulfonylation of unactivated alkenes under mild reaction conditions with good functional-group tolerance in the most atom-economic manner by using readily available Ag(O2CCF2SO2F) and N-fluorobenzenesulfonimide (NFSI). Both the trifluoromethyl and sulfonyl groups in the products originate from Ag(O2CCF2SO2F).

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.

METHOD FOR PREPARING A SULFONIMIDE COMPOUND AND SALTS THEREOF

The present invention relates to a method for preparing an aqueous sulfonimide compound of the formula (Rf1—SO2) (Rf2—SO2)NH, wherein Rf1et Rf2 are independently selected from the group comprising: a fluorine atom and groups having 1 to 10 carbon atoms selected from the perfluoroalkyl, fluoroalkyl, fluoroalkenyl and fluoroallyl groups, from a mixture M1 including (Rf1—SO2)(Rf2—SO2)NH, Rf1SO2H and/or Rf2SO2H, Rf1SO2NH2 and/or Rf2SO2NH2, characterized in that said method includes an oxidation step of said mixture M1 using an oxidizing agent in order to obtain a mixture M2 including (Rf1—SO2)(Rf2—SO2)NH, Rf1SO3H and/or Rf2SO3H, and Rf1SO2NH2 and/or Rf2SO2NH2.

FLUOROALKANESULFONIC ACID PRODUCTION METHOD

Disclosed is a method for producing a fluoroalkanesulfonic acid including (1) the step of reacting concentrated sulfuric acid and/or fuming sulfuric acid with a fluoroalkanesulfonate to cause an acid decomposition, thereby obtaining a reaction mixture containing the fluoroalkanesulfonic acid and a sulfur component; and (2) the step of adding an oxidizing agent to the reaction mixture obtained by the above step and then conducting a distillation, thereby obtaining the fluoroalkanesulfonic acid from the reaction mixture. It is possible by this method to efficiently reduce the sulfur component, thereby industrially advantageously obtaining fluoroalkanesulfonic acid of high purity.