Trifluoromethanesulfonimide Chemical Properties

Melting point:

52-56 °C

Boiling point:

90-91 °C(lit.)

Density 

1.36

storage temp. 

2-8°C

solubility 

800g/l Risk of violent reaction.

form 

Crystals

pka

-10.42±0.40(Predicted)

color 

Colorless to brownish

PH

0.8 (100g/l, H2O, 20℃)Risk of violent reaction.

BRN 

4754101

Stability:

Stable. Incompatible with strong oxidizing agents. Reacts violently with water.

InChIKey

ZXMGHDIOOHOAAE-UHFFFAOYSA-N

LogP

-0.771 at 25.5℃ and pH6.7

CAS DataBase Reference

82113-65-3(CAS DataBase Reference)

EPA Substance Registry System

Methanesulfonamide, 1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]- (82113-65-3)

Safety Information

Hazard Codes 

C

Risk Statements 

34-40-14-67-37

Safety Statements 

26-36/37/39-45-8

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

F 

3-10-21

Hazard Note 

Corrosive

HazardClass 

8

PackingGroup 

I

HS Code 

29350090

MSDS

• Language:English Provider:SigmaAldrich

Trifluoromethanesulfonimide Usage And Synthesis

Chemical Properties

light yellow to brown liquid

Uses

1,1,1-Trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide is commonly used as a strong acid to prepare Lewis Acid catalysts. It can also be used to improve efficiency of graphene/silicon Schottky solar cells by chemical doping and as a solvent for recycling battery electrodes.

Uses

Trifluoromethanesulfonimide may be used as a catalyst for the preparation of 1-substituted-1H-1,2,3,4-tetrazoles.

Uses

Trifluoromethanesulfonimide is a strong acid, used in the preparation of highly efficient Lewis acid catalysts.

Application

Trifluoromethanesulfonimide may be used in the following studies:
As catalyst during the polymerization of octamethylcyclotetrasiloxane in the presence of hexamethyldisiloxane.
As efficient catalyst in the synthesis of various non-reducing disaccharides, via ketopyranosylation of 2,3,4,6-tetra-O-benzyl-1-C-methyl-D-hexopyranoses.
Starting material for preparing the N-fluoro derivative, a reactive fluorinating agent.
As a component of solid polymer electrolytes.

General Description

Bis(trifluoromethane)sulfonimide (TFSI, Tf₂N) is utilized as anion species to form 1-ethyl-3-methylimidazolium molten salts. It undergoes acid-base complexation with rod-like poly(2,5-pyridine) to afford highly-ordered lamellar self-assemblies in the hydrated films.

Synthesis

The general procedure for the synthesis of lithium bis(trifluoromethanesulfonyl)imide (HTf2N) from lithium bis(trifluoromethanesulfonyl)imide (LiTf2N) is as follows: LiTf2N is dissolved in concentrated sulfuric acid, followed by sublimation at 70 °C under reduced pressure (10^-3 mbar) to give the HTf2N crude product. This crude product can be further purified. The yield was 90%. The NMR hydrogen spectrum (1H-NMR, D2O) of the product showed: δ 4.77 (s, 1H); the NMR fluorine spectrum (19F-NMR, D2O) showed: δ -79.16 (s, 6F); and the NMR carbon spectrum (13C{19F}NMR, D2O) showed: δ 119.27 (s, 2C).

References

[1] Journal fuer Praktische Chemie/Chemiker-Zeitung, 1998, vol. 340, # 6, p. 506 - 512
[2] Physical Chemistry Chemical Physics, 2011, vol. 13, # 2, p. 725 - 731
[3] Journal of Fluorine Chemistry, 2007, vol. 128, # 10, p. 1326 - 1334
[4] Chemistry - A European Journal, 2010, vol. 16, # 11, p. 3355 - 3365
[5] Journal of Molecular Liquids, 2014, vol. 192, p. 191 - 198

Trifluoromethanesulfonimide(82113-65-3)Related Product Information

• Bis(4-biphenylyl)amine
• Bis(triphenylphosphine)palladium(II) chloride
• Didecyl dimethyl ammonium chloride
• Didecyldimethylammonium bromide
• Dicyclopropane methylamine
• Triethylsulfonium bis(trifluoromethylsulfonyl)imide
• Trifluoromethanesulfonimide
• 1-BUTYL-1-METHYLPYRROLIDINIUM BIS(TRIFLUOROMETHYLSULFONYL)IMIDE
• N-(5-CHLORO-2-PYRIDYL)BIS(TRIFLUOROMETHANESULFONIMIDE)
• 1-BUTYL-3-METHYLIMIDAZOLIUM BIS(TRIFLUOR
• N-Phenyl-bis(trifluoromethanesulfonimide)
• TRIHEXYL(TETRADECYL)PHOSPHONIUM BIS(TRIFLUOROMETHYLSULFONYL)IMIDE
• N-(2-PYRIDYL)BIS(TRIFLUOROMETHANESULFONIMIDE)
• 1-ETHYL-3-METHYLIMIDAZOLIUM BIS(TRIFLUOROMETHYLSULFONYL)IMIDE
• Lithium bis(trifluoromethanesulphonyl)imide
• MAGNESIUM TRIFLUOROMETHANESULFONIMIDE
• Methanesulfonamide
• Trifluoromethane