684-10-6

Usage

Uses

Used in Pharmaceutical Industry:
TRIFLUOROETHENESULFONYL FLUORIDE is used as a reagent for the synthesis of pharmaceutical compounds. Its ability to introduce fluorine and trifluoromethyl groups into organic molecules enhances the properties of these compounds, leading to the development of more effective drugs.
Used in Agrochemical Industry:
In the agrochemical industry, TRIFLUOROETHENESULFONYL FLUORIDE is utilized as a reagent in the production of various agrochemical compounds. Its fluorinating and trifluoromethylating capabilities contribute to the creation of more potent and efficient agrochemicals for agricultural applications.
Used in Polymer Industry:
TRIFLUOROETHENESULFONYL FLUORIDE is employed in the preparation of fluorinated polymers. The incorporation of fluorine atoms into polymer structures results in materials with improved chemical resistance, thermal stability, and non-stick properties, making them suitable for various applications, such as coatings and membranes.
Used in Specialty Chemicals Production:
As a precursor for specialty chemicals, TRIFLUOROETHENESULFONYL FLUORIDE is used in the synthesis of unique and high-value compounds for specific applications. Its reactivity allows for the formation of complex molecules that are otherwise difficult to obtain through conventional methods.

InChI:InChI=1/C2F4O2S/c3-1(4)2(5)9(6,7)8

Synthetic route

1,2-dichlorotrifluoroethane-1-sulfonylfluoride (7740-56-9) → perfluorovinyl-sulfonyl fluoride (684-10-6)

Conditions	Yield
With Zn In 1,4-dioxane with HCl activated Zn, with Na dryed dioxane;	92%
With zinc In 1,4-dioxane at 45℃; for 48h;

1,2,2,2-tetrafluoro-ethanesulfonyl fluoride (2127-74-4) → perfluorovinyl-sulfonyl fluoride (684-10-6)

Conditions	Yield
With potassium chloride; chromium(III) oxide at 510℃;

1,2,2-trifluoro-2-hydroxy-1-fluorosulfonylethanesulphonic acid sultone (155652-55-4) → Carbonyl fluoride (353-50-4) + perfluorovinyl-sulfonyl fluoride (684-10-6) + 2-fluoro-2,2-bis(fluorosulfonyl)ethanoyl fluoride

Conditions	Yield
1.) 120 deg C, 6 d, 2.) 220 deg C, 6 d; Yield given. Yields of byproduct given;

perfluoropropylene (116-15-4) + sulfur trioxide (7446-11-9) → perfluorovinyl-sulfonyl fluoride (684-10-6)

Conditions	Yield
With H2O; KCl-Cr2O3 catalyst byproducts: HF; cyclic sulfone obtained at 150°C, 2 h, on refluxing with H2O yields CF3CHFSO2F which in gas phase at 506-510°C, pressure 5-40 Torr, and presence of KCl-Cr2O3 splits off HF;	50-60
With water byproducts: HF; cyclic sulfone obtained at 150°C, 2 h, on refluxing with H2O yields CF3CHFSO2F which in gas phase at 506-510°C, pressure 5-40 Torr, and presence of KCl-Cr2O3 splits off HF;	50-60

bis-trifluoromethyl-aminooxyl (2154-71-4) + perfluorovinyl-sulfonyl fluoride (684-10-6) → 1,2-bis(N,N-bis(trifluoromethyl)aminoxy)-trifluoroethanesulfonyl fluoride (52193-61-0)

Conditions	Yield
20°C, 48 h;	91%
20°C, 48 h;	91%

perfluorovinyl-sulfonyl fluoride (684-10-6) + hydrogen bromide (10035-10-6, 12258-64-9) → 2-bromo-1,2,2-trifluoro-ethanesulfonyl fluoride (7740-80-9)

Conditions	Yield
80°C , 17 h,in presence of azo-bis-isobutyronitrile;	89%

perfluorovinyl-sulfonyl fluoride (684-10-6) + bromine (7726-95-6) → 1,2-dibromotrifluoroethane-1-sulfonylchloride (7740-55-8)

Conditions	Yield
Irradiation (UV/VIS); 3 min;	84%

perfluorovinyl-sulfonyl fluoride (684-10-6) + sodium carbonate (497-19-8) → CF2CFSO2O(1-)*Na(1+)=CF2CFSO2ONa (7740-77-4)

Conditions	Yield
20°C, 18 h;	74%

perfluorovinyl-sulfonyl fluoride (684-10-6) + sodium hydroxide (1310-73-2) → CF2CFSO2O(1-)*Na(1+)=CF2CFSO2ONa (7740-77-4)

Conditions	Yield
20°C, 18 h;	67%

perfluorovinyl-sulfonyl fluoride (684-10-6) + hydrogen fluoride (7664-39-3) → 1,2,2,2-tetrafluoro-ethanesulfonyl fluoride (2127-74-4)

Conditions	Yield
60°C , 3 h;	61%
60°C , 3 h;	61%

potassium fluoride + perfluorovinyl-sulfonyl fluoride (684-10-6) → 1,2,2,2-tetrafluoro-ethanesulfonyl fluoride (2127-74-4)

Conditions	Yield
In formamide Irradiation (UV/VIS); 35°C , 20 h , irradiation of volatile product in presence of bromine;	41%

perfluorovinyl-sulfonyl fluoride (684-10-6) → carbon dioxide (124-38-9) + carbon monoxide (201230-82-2) + sulfur dioxide (7446-09-5) + silicon tetrafluoride (7783-61-1)

Conditions	Yield
byproducts: rest; 200°C, 14 days; determination: IR;	A <1 B n/a C 17% D n/a

methanol (67-56-1) + perfluorovinyl-sulfonyl fluoride (684-10-6) → <1,1,2-Trifluor-1-methoxy-aethyl>-sulfonsaeure-fluorid (7740-78-5)

Conditions	Yield
at 0℃;
0°C;

perfluorovinyl-sulfonyl fluoride (684-10-6) → 1,2,2,2-tetrafluoro-ethanesulfonyl fluoride (2127-74-4)

Conditions	Yield
With hydrogen fluoride at 60℃; for 72h;

perfluorovinyl-sulfonyl fluoride (684-10-6) → 2-bromo-1,2,2-trifluoro-ethanesulfonyl fluoride (7740-80-9)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); hydrogen bromide at 80℃; for 17h;

perfluorovinyl-sulfonyl fluoride (684-10-6) → 1,2-dichlorotrifluoroethane-1-sulfonylfluoride (7740-56-9)

Conditions	Yield
With chlorine Irradiation;

perfluorovinyl-sulfonyl fluoride (684-10-6) → 1,2-dibromotrifluoroethane-1-sulfonylchloride (7740-55-8)

Conditions	Yield
With bromine Irradiation;

perfluorovinyl-sulfonyl fluoride (684-10-6) + diethylamine (109-89-7) → 2-diethylamino-1-H-trifluoroethanesulfonyl fluoride (42937-18-8)

perfluorovinyl-sulfonyl fluoride (684-10-6) → 2-fluoro-2,2-bis(fluorosulfonyl)ethanoyl fluoride + Fluorosulfuric acid fluoro-fluorocarbonyl-fluorosulfonyl-methyl ester + 1,2,2-trifluoro-2-hydroxy-1-fluorosulfonylethanesulphonic acid sultone (155652-55-4)

Conditions	Yield
With sulfur trioxide at 120℃; for 40h;	A 20 % Spectr. B 2.7 % Spectr. C 77 % Spectr.

perfluorovinyl-sulfonyl fluoride (684-10-6) + chlorine (7782-50-5) → 1,2-dichlorotrifluoroethane-1-sulfonylfluoride (7740-56-9)

Upstream product

• 7740-56-9 1,2-dichlorotrifluoroethane-1-sulfonylfluoride 
• 116-15-4 perfluoropropylene 
• 7446-11-9 sulfur trioxide 
• 155652-55-4 1,2,2-trifluoro-2-hydroxy-1-fluorosulfonylethanesulphonic acid sultone 
• 2127-74-4 1,2,2,2-tetrafluoro-ethanesulfonyl fluoride 

Downstream Products

• 124-38-9 carbon dioxide 
• 201230-82-2 carbon monoxide 
• 7446-09-5 sulfur dioxide 
• 7783-61-1 silicon tetrafluoride 

Relevant academic research and scientific papers

Synthesis and reactions of the β-sultone of perfluorovinylsulfonyl fluoride

Reactions of perfluorovinylsulfonyl fluoride, CF2=CFSO2F (1), with SO3 forms the novel β-sultone cyclo (2) in good yield.Compound 2 undergoes ring-opening upon heating or reaction with fluoride ion to give F(O)C-CF(SO2F)2 (3).Hydrolysis of 3 and 2 yields the new compounds CHF(SO2F)2 (4) and HO3S-CHF-SO2F (5), respectively.

Process for preparing perfluoroalkenyl sulfonyl fluorides

Described in a process for the preparation of perfluoroalkenyl sulfonyl fluorides of formula:, Rf-CF=CF-SO2F, wherein:, Rfis F or a perfluoroalkyl group of from 1 to 9 carbon atoms,comprising the contacting of a compound of formula, Rf-CF2-CF(COF)-SO2F, with a reactant selected from carbonates of metals belonging to Groups IA, IIA and IIB of the Periodic Table of Elements at a temperature of from about 150 to about 400°C.

Perfluoroallyl fluorosulfate and its sultone and polymers

Hexafluoropropene is reacted with liquid sulfur trioxide in the presence of boric oxide, boron trichloride, boron trifluoride, tri(lower alkyl) borate, boron trioxychloride or boron trioxyfluoride at from 0° C. to 150° C. to form perfluoroallyl fluorosulfate and the sultone thereof. The perfluoroallyl fluorosulfate can be homopolymerized or copolymerized with various fluoroethylenes to form resins useful as ion exchange resins or catalysts. The fluorosulfate groups on the resins can be hydrolyzed to form carboxylic acid groups or various corresponding salts. The sultone of perfluoroallyl fluorosulfate can be rearranged to form β-fluorocarbonyl-β-fluorosulfonyl-trifluorethyl fluorosulfate.