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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.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

212.0 °F

flash_point_c

> 100 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Efficient Air?Stable Organometallic Low?Molecular?Mass Gelators for Ionic Liquids: Synthesis, Aggregation and Application of Pyridine?Bridged Bis (benzimidazolylidene)?Palladium Complexes.
Tu T, et al.
Chemistry?A European Journal, 15(8), 1853-1861 (2009)
[bmim][OTf]: a versatile room temperature glycosylation promoter.
Galan M C, et al.
Tetrahedron Letters, 50(4), 442-445 (2009)
A new application of Baylis?Hillman alcohols to a diastereoselective synthesis of 3-nitrothietanes.
Rai A and Yadav L D S
Tetrahedron, 68(11), 2459-2464 (2012)
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)
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)
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