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Sigma-Aldrich

1-Butyl-3-methylimidazolium trifluoromethanesulfonate

97%

Synonym(s):

BMIM Otf

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About This Item

Empirical Formula (Hill Notation):
C9H15F3N2O3S
CAS Number:
174899-66-2
Molecular Weight:
288.29
MDL number:
MFCD03427620
UNSPSC Code:
12352100
PubChem Substance ID:
329763088
NACRES:
NA.22

Quality Level

100

Assay

97%

form

liquid

impurities

≤0.5% water

refractive index

n20/D 1.434

density

1.292 g/mL at 20 °C (lit.)

SMILES string

[O-]S(=O)(=O)C(F)(F)F.CCCCn1cc[n+](C)c1

InChI

1S/C8H15N2.CHF3O3S/c1-3-4-5-10-7-6-9(2)8-10;2-1(3,4)8(5,6)7/h6-8H,3-5H2,1-2H3;(H,5,6,7)/q+1;/p-1

InChI key

FRZPYEHDSAQGAS-UHFFFAOYSA-M

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General description

1-Butyl-3-methylimidazolium trifluoromethanesulfonate [bmim][OTf] is a versatile ionic liquid commonly used in synthetic chemistry.

Application

[bmim][OTf] can be used as:       
  • A glycosylation promoter in the synthesis of oligosaccharides from thiophenyl and trichloroacetimidate glycoside donors.      
  •  A solvent for the extraction of sulfur and nitrogen containing aromatic organic compounds from aliphatic hydrocarbons.
  •   A reagent in the preparation of ion-conductive polymeric membranes.        
  • A dopant in the synthesis of poly (ethyl methacrylate) based polymer electrolytes to increase the ionic conductivity.
  •  A reaction medium to synthesize aryl ketones by Friedel–Crafts benzoylation of aryl compounds by using bismuth triflate as a catalyst.

WGK

WGK 3

Flash Point(F)

>212.0 °F

Flash Point(C)

> 100 °C

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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Selective Quenching of 2-Naphtholate Fluorescence by Imidazolium Ionic Liquids.
Kumar V and Pandey S
The Journal of Physical Chemistry B, 116(39), 12030-12037 (2012)
Preparation and characterization of poly (ethyl methacrylate) based polymer electrolytes doped with 1-butyl-3-methylimidazolium trifluoromethanesulfonate
Ramesh S, et al.
MEASUREMENT, 48, 263-273 (2014)
Ion-conductive polymer membranes containing 1-butyl-3-methylimidazolium trifluoromethanesulfonate and 1-ethylimidazolium trifluoromethanesulfonate
Schauer J, et al.
Journal of Membrane Science , 367(1-2), 332-339 (2011)
tert-Amyl ethyl ether separation from its mixtures with ethanol using the 1-butyl-3-methylimidazolium trifluoromethanesulfonate ionic liquid: liquid- liquid equilibrium
Arce A, et al.
Industrial & Engineering Chemistry Research, 43(26), 8323-8327 (2004)
A study of new anhydrous, conducting membranes based on composites of aprotic ionic liquid and cross-linked SPEEK for fuel cell application.
Malik R S, et al.
Electrochimica Acta, 152, 352-359 (2015)
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