684-10-6

Basic information

• Product Name: TRIFLUOROETHENESULFONYL FLUORIDE
• Synonyms: (trifluoroethylene)sulfonylfluoride;ethenesulfonylfluoride,trifluoro-;perfluoroethylenesulfonylfluoride;TRIFLUOROETHENESULFONYL FLUORIDE;TRIFLUOROVINYLSULFONYL FLUORIDE;Trifluoroethenesufonyl fluoride
• CAS NO: 684-10-6
• Molecular Formula: C₂F₄O₂S
• Molecular Weight: 164.08
• Mol File: 684-10-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 53 °C
• Flash Point: 0.4°C
• Appearance: /
• Density: 1.652
• Vapor Pressure: 108mmHg at 25°C
• Refractive Index: 1.332
• CAS DataBase Reference: TRIFLUOROETHENESULFONYL FLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIFLUOROETHENESULFONYL FLUORIDE(684-10-6)
• EPA Substance Registry System: TRIFLUOROETHENESULFONYL FLUORIDE(684-10-6)

Safety Data

• Hazard Codes: Xi,C
• HazardClass: IRRITANT, CORROSIVE
• Hazardous Substances Data: 684-10-6(Hazardous Substances Data)

Usage

General Description

TRIFLUOROETHENESULFONYL FLUORIDE is a chemical compound with the molecular formula C2F3O2S and is commonly referred to as TFESF. It is a colorless, highly reactive and toxic compound that is used as a fluorinating and trifluoromethylating agent in organic synthesis. TFESF is commonly used in the pharmaceutical and agrochemical industries as a reagent in the production of various compounds. It is also used in the preparation of fluorinated polymers and as a precursor for specialty chemicals. TFESF is highly reactive and must be handled with caution in a controlled laboratory setting.

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

• 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 
• 7740-56-9 1,2-dichlorotrifluoroethane-1-sulfonylfluoride 

Downstream Products

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

Relevant articles and documents

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.

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.