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Merck
CN

711772

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
NACRES:
NA.22
PubChem Substance ID:
329763088
UNSPSC Code:
12352100
MDL number:
MFCD03427620

Key Documents

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Product Name

1-Butyl-3-methylimidazolium trifluoromethanesulfonate, 97%

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

SMILES string

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

InChI key

FRZPYEHDSAQGAS-UHFFFAOYSA-M

assay

97%

form

liquid

impurities

≤0.5% water

refractive index

n20/D 1.434

density

1.292 g/mL at 20 °C (lit.)

functional group

fluoro
triflate

Quality Level

100

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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.

General description

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

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

>212.0 °F

flash_point_c

> 100 °C

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP0549
BCBT2495
BCCJ0239
BCBT0561
BCBN9368V

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[bmim][OTf]: a versatile room temperature glycosylation promoter.
Galan M C, et al.
Tetrahedron Letters, 50(4), 442-445 (2009)
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)
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)
Improvement of the Friedel-Crafts benzoylation by using bismuth trifluoromethanesulfonate in 1-butyl-3-methylimidazolium trifluoromethanesulfonate ionic liquid under microwave irradiation
Tran PH, et al.
Tetrahedron Letters, 55(1), 205-208 (2014)
Deep fuels desulfurization and denitrogenation using 1-butyl-3-methylimidazolium trifluoromethanesulfonate
Ke?dra-Krolik K, et al.
Energy & Fuels, 25(4), 1559-1565 (2011)
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