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Sigma-Aldrich

1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide

≥97.0% (NMR)

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Synonym(s):
EMIM BTI, EMIM TFSI, EMIMIm
Empirical Formula (Hill Notation):
C8H11F6N3O4S2
CAS Number:
Molecular Weight:
391.31
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥97.0% (NMR)

form

solid

impurities

<0.5% water

mp

≥−15 °C (lit.)

SMILES string

CCn1cc[n+](C)c1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F

InChI

1S/C6H11N2.C2F6NO4S2/c1-3-8-5-4-7(2)6-8;3-1(4,5)14(10,11)9-15(12,13)2(6,7)8/h4-6H,3H2,1-2H3;/q+1;-1

InChI key

LRESCJAINPKJTO-UHFFFAOYSA-N

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This Item
564869008014.90189
form

solid

form

-

form

liquid

form

liquid

mp

≥−15 °C (lit.)

mp

-

mp

≥−15 °C (lit.)

mp

-15 °C

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

200

impurities

<0.5% water

impurities

-

impurities

≤500 ppm H2O

impurities

-

General description

1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [EMIM][N(Tf)2] is a room temperature ionic liquid (RTIL). ([EMIM][N(Tf)2]) as a non-aqueous solvent, is advantageous over traditional aprotic polar organic solvents in electrochemical investigation of electroactive species since it has low vapor pressure, high thermal stability, good conductivity and a wide electrochemical window. [EMIM][N(Tf)2] shows good solubility in CO2.

Application

[EMIM][N(Tf)2] may be used as a green solvent for the synthesis of zinc oxide (ZnO) nanoparticles under microwave conditions. It is useful in reactions which need a solvent with high CO2 solubility.

Physical form

fluorinated, hydrophobic ionic liquid

Other Notes

Enantioselective reactions in ionic liquids

Legal Information

Product protected by U.S. Patent 5,827,602 assigned to Covalent Associates, Inc. Woburn, Ma, USA

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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J.M. Fraile et al.
Tetrahedron Asymmetry, 12, 1891-1891 (2001)
Pedro Lozano et al.
Chemical communications (Cambridge, England), (7), 692-693 (2002-07-18)
Soluble Candida antarctica lipase B dissolved in ionic liquids showed good synthetic activity, enantioselectivity and operational stability in supercritical carbon dioxide for both butyl butyrate synthesis and the kinetic resolution of 1-phenylethanol processes by transesterification.
Determination of ammonia based on the electro-oxidation of hydroquinone in dimethylformamide or in the room temperature ionic liquid, 1-ethyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide.
Giovanelli D, et al.
Talanta, 62(5), 904-911 (2004)
Thermodynamic properties of mixtures containing ionic liquids. 3. Liquid? liquid equilibria of binary mixtures of 1-ethyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide with propan-1-ol, butan-1-ol, and pentan-1-ol
Heintz, Andreas, Jochen K. Lehmann, and Christiane Wertz
Journal of Chemical and Engineering Data, 48.3, 472-474 (2003)
Raman and ab initio study of the conformational isomerism in the 1?ethyl?3?methyl?imidazolium bis (trifluoromethanesulfonyl) imide ionic liquid
Lassegues, J. C., et al.
Journal of Raman Spectroscopy, 38.5, 551-558 (2007)

Articles

Over the past decade, Ionic Liquids have attracted much interest for their use as non-aqueous electrolytes in electrochemical applications. In this context, their conductivity as well as their electrochemical stability are the most important physical properties.

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