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15220

Sigma-Aldrich

Bis(trifluoromethane)sulfonimide

purum, ≥95.0% (19F-NMR)

Synonym(s):

Bis(trifluoromethanesulfonyl)amine, Bis(trifluoromethylsulfonyl)amine

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About This Item

Linear Formula:
(CF3SO2)2NH
Molecular Weight:
281.15
Beilstein:
4754101
MDL number:
MFCD00214154
UNSPSC Code:
12352101
PubChem Substance ID:
329750774
NACRES:
NA.22

grade

purum

Quality Level

100

Assay

≥95.0% (19F-NMR)

form

solid

mp

52-56 °C
61-65 °C

SMILES string

FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F

InChI

1S/C2HF6NO4S2/c3-1(4,5)14(10,11)9-15(12,13)2(6,7)8/h9H

InChI key

ZXMGHDIOOHOAAE-UHFFFAOYSA-N

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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.

Application

Bis(trifluoromethane)sulfonamide 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.

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301,H318,H412

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Dam. 1

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2431
BCCK0956
BCCH2371
BCCD2542
BCCB0678

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Comparative Electrochemical Study of New Poly(oxyethylene)-Li Salt Complexes.
Benrabah D, et al.
J. Chem. Soc., Faraday, 89, 355-359 (1993)
Self-assembly of cationic rod-like poly (2, 5-pyridine) by acidic bis (trifluoromethane) sulfonimide in the hydrated state: A highly-ordered self-assembled protonic conductor.
Vilkman M, et al.
Polymer, 51(18), 4095-4102 (2010)
Bis (trifluoromethane) sulfonimide initiated ring-opening polymerization of octamethylcyclotetrasiloxane.
Desmurs J-R, et al.
Journal of Organometallic Chemistry, 646(1), 171-178 (2002)
N-Fluorobis[(perfluoroalkyl)sulfonyl]imides: Reactions with some olefins via α-fluoro carbocationic intermediates.
Desmarteau DD, et al.
The Journal of Organic Chemistry, 57(2), 629-635 (1992)
Synthesis of trehalose mimics by bismuth (III) triflate or bis (trifluoromethane) sulfonimide-catalyzed 1-C-methyl-D-hexopyranosylation.
Yamanoi T, et al.
Tetrahedron Asymmetry, 17(20), 2914-2918 (2006)
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