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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:
174899-82-2
Molecular Weight:
391.31
MDL number:
MFCD03788927
UNSPSC Code:
12352100
PubChem Substance ID:
329749349
NACRES:
NA.22

Quality Level

100

Assay

≥97.0% (NMR)

form

liquid

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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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
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310 + P330

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
Liquid? liquid equilibria in binary mixtures containing substituted benzenes with ionic liquid 1-ethyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide
Shiflett, Mark B., and Anne Marie S. Niehaus
Journal of Chemical and Engineering Data, 55.1, 346-353 (2009)
Investigation on physical and electrochemical properties of three imidazolium based ionic liquids (1-hexyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide and 1-butyl-3-methylimidazolium methylsulfate)
Beigi, Ali Akbar Miran, et al.
Journal of Molecular Liquids, 177, 361-368 (2013)
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)
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