1-Butyl-3-methylimidazolium hexafluorophosphate

1-Butyl-3-methylimidazolium hexafluorophosphate
  • CAS No.:174501-64-5
Other grades of this product :
1-Butyl-3-methylimidazolium hexafluorophosphate Basic information
Product Name:1-Butyl-3-methylimidazolium hexafluorophosphate
Synonyms:1-Butyl-3-methylimidazolium hexafluorophosphate≥ 98.5%(HPLC);1-BUTYL-3-METHYLIMIDAZOLIUM HEXAFLUOROPHOSPHATE;1-BUTYL-3-METHYLIMIDAZOLIUM HEXFLUOROPHOSPHATE;1-Butyl-3-MethyliMidazoliuM hexafluorophosphate >=97.0% (HPLC);1-butyl-3-methylimmidazolium hexafluorophosphate;1-Butyl-3-methylimidazolium hexafluorophosphate for catalysis, >=98.5% (T);1-butyl-3-methylimidazolium hexafluorophsphate;JACS-174501-64-5
CAS:174501-64-5
MF:C8H15F6N2P
MW:284.18
EINECS:678-095-9
Product Categories:Ionic liquid;Imidazolium Compounds;Imidazolium Salts (Ionic Liquids);Ionic Liquids;Synthetic Organic Chemistry
Mol File:174501-64-5.mol
1-Butyl-3-methylimidazolium hexafluorophosphate Chemical Properties
Melting point 6.5 °C
Boiling point >340°C
density 1.38 g/mL at 20 °C (lit.)
refractive index n20/D 1.41
Fp >350°C
storage temp. Store below +30°C.
solubility Acetone, Methanol
form Viscous Liquid
Specific Gravity1.396
color Clear colorless to pale yellow
PH5 (H2O, 20℃)
Water Solubility Miscible with dichloromethane, chloroform, ethyl acetate. Immiscible with water, diethyl ether and hexane.
Hydrolytic Sensitivity4: no reaction with water under neutral conditions
Merck 14,1581
InChIKeyIXQYBUDWDLYNMA-UHFFFAOYSA-N
CAS DataBase Reference174501-64-5(CAS DataBase Reference)
ECW4.2 V
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-22
Safety Statements 26-37/39
WGK Germany 3
3-10
TSCA No
HazardClass IRRITANT
HS Code 29339900
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
1-Butyl-3-methylimidazolium hexafluorophosphate Usage And Synthesis
Conductivity1.92 mS/cm
Chemical PropertiesClear pale yellow oil
Usesthose consisting of tetrafluoroborate, alkylsulfate, alkylsulfonate, carboxylate, or phosphate anions are hydrophilic and are completely dissolved in water. Dupont and coworkers first reported stable hydrophobic imidazolium salt, 1-butyl-3-methylimidazolium hexafluorophosphate ([C4mim][PF6]) in 1996. Since then, this salt has been used as a typical hydrophobic IL in many chemical reactions because its mixture with water forms a biphasic layer. Furthermore, this IL shows poor solubility in hexane or ether, which allows realization of an easy work-up process. However, [C4mim][PF6] was reported to be sensitive to the moisture at high temperature and produced hazardous hydrogen fluoride as it decomposed. Therefore, bis(trifluoromethanesulfonyl)amide (NTf2) salts are now recommended as the anion for preparing hydrophobic ILs.
Uses1-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.
General Description1-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.

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