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70956

Sigma-Aldrich

1-Butyl-3-methylimidazolium hexafluorophosphate

≥97.0% (HPLC)

Synonym(s):
BMIMPF6
Empirical Formula (Hill Notation):
C8H15F6N2P
CAS Number:
Molecular Weight:
284.18
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥97.0% (HPLC)

refractive index

n20/D 1.411 (lit.)

density

1.38 g/mL at 20 °C (lit.)

SMILES string

F[P-](F)(F)(F)(F)F.CCCCn1cc[n+](C)c1

InChI

1S/C8H15N2.F6P/c1-3-4-5-10-7-6-9(2)8-10;1-7(2,3,4,5)6/h6-8H,3-5H2,1-2H3;/q+1;-1

InChI key

IXQYBUDWDLYNMA-UHFFFAOYSA-N

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General description

1-Butyl-3-methylimidazolium hexafluorophosphate is an imidazolium-based, hydrophobic, room temperature ionic liquid (RTIL). It can be prepared by reacting 1-methylimidazole with chlorobutane. Gaseous hydrofluorocarbons (HFCs) such as fluoromethane, fluoroethane and 1,1,2,2-tetrafluoroethane are soluble in BMIMPF6.

Application

1-Butyl-3-methylimidazolium hexafluorophosphate is an ionic liquid employed in many environmentally friendly reactions.

It can also be used as a medium for reactions such as:
  • Ring-closing metathesis of diene and enyne substrates in the presence of a novel recyclable ruthenium carbene complex.
  • Nickel(II)acetylacetonate catalyzed oxidation of aromatic aldehydes to the corresponding acids using dioxygen as the oxidant.
  • Lipase-catalyzed enantioselective acylation of allylic alcohols.
  • Allylation of aldehydes using tetraallylstannane to yield homoallylic alcohols.

Packaging

5, 50, 250 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Lipase-catalyzed enantioselective acylation in the ionic liquid solvent system: reaction of enzyme anchored to the solvent.
Itoh T, et al.
Chemistry Letters (Jpn), 30(3), 262-263 (2001)
Solvent properties of the 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid.
Carda-Broch S, et al.
Analytical and Bioanalytical Chemistry, 375(2), 191-199 (2003)
Ali R Jalalvand et al.
International journal of biological macromolecules, 79, 1004-1010 (2015-06-04)
A novel biosensor for detecting DNA damage induced by benzo(a)pyrene (BP) and its metabolite was presented in this work. The nafion-solubilized single wall carbon nanotubes-ionic liquid (SWCNTs-NA-IL) composite film was prepared and then horseradish peroxidase (HRP) and double-stranded DNA were...
Olefin Metathesis in the Ionic Liquid 1?Butyl?3?methylimidazolium Hexafluorophosphate Using a Recyclable Ru Catalyst: Remarkable Effect of a Designer Ionic Tag.
Yao Q and Zhang Y
Angewandte Chemie (International Edition in English), 42(29), 3395-3398 (2003)
Diffusivities of gases in room-temperature ionic liquids: data and correlations obtained using a lag-time technique.
Morgan D, et al.
Industrial & Engineering Chemistry Research, 44(13), 4815-4823 (2005)

Protocols

Enzymatic Reactions in Ionic Liquids

One of the most popular lipase for synthetic use is the Candida antarctica lipase (CALB). CALB catalyzes the enantioselective acylation of 1-phenylethylamine with 4-pentenoic acid

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