1-butyl-3-methyl-1H-imidazol-3-ium; hexafluoro-$l^{5}-phosphanuide

• ChemBase ID: 11867
• Molecular Formular: C8H15F6N2P
• Molecular Mass: 284.1822802
• Monoisotopic Mass: 284.08770444
• SMILES: c1[n+](cn(c1)CCCC)C.[P-](F)(F)(F)(F)(F)F
• Canonical SMILES: F[P-](F)(F)(F)(F)F.CCCCn1cc[n+](c1)C
• InChI: 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
• InChIKey: IXQYBUDWDLYNMA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-butyl-3-methyl-1H-imidazol-3-ium; hexafluoro-$l^{5}-phosphanuide; 1-butyl-3-methyl-1H-imidazol-3-ium; hexafluoro-λ^5-phosphanuide
• IUPAC Traditional name: 1-butyl-3-methylimidazolium; hexafluoro-$l^{5}-phosphanuide; C4mim; hexafluoro-$l^{5}-phosphanuide; 1-butyl-3-methylimidazolium hexafluorophosphate; 1-butyl-3-methylimidazolium; hexafluoro-λ^5-phosphanuide
• Synonyms: 1-Butyl-3-methylimidazolium hexafluorophosphate; 1-Butyl-3-methylimidazol-3-ium hexafluorophosphate 97%; BMIMPF6; 1-Butyl-3-methylimidazolium hexafluorophosphate; BMIM-PF₆; 1-n-Butyl-3-methylimidazolium hexafluorophosphate; 1-Butyl-3-methyl-1H-imidazol-3-ium hexafluorophosphate(V); 1-丁基-3-甲基咪唑六氟磷酸盐; 1-正-丁基-3-甲基咪唑鎓六氟磷酸盐

Database IDs

• CAS Number: 174501-64-5
• EC Number: 000-000-0
• MDL Number: MFCD03093295
• Merck Index: 141581
• PubChem SID: 160975174; 24886139; 24850922
• PubChem CID: 2734174
• Chemspider ID: 2015930
• Wikipedia Title: 1-Butyl-3-methylimidazolium_hexafluorophosphate

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): -2.1459775
• LogD (pH = 7.4): -2.1459775
• Log P: -2.1459775
• Molar Refractivity: 42.7263 cm^3
• Polarizability: 16.443125 Å^3
• Polar Surface Area: 8.81 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: insoluble in water
• Apperance: Light yellow liquid
• Melting Point: 6-7°C; 8°C; 8-10°C
• Boiling Point: >340(dec.)°C; >350°C; >350°C
• Density: 1.365; 1.38; 1.38 g/mL (20 °C); 1.38 g/mL at 20 °C(lit.)
• Refractive Index: 1.4115; n20/D 1.41; n20/D 1.411

Safety Information

• Storage Warning: IRRITANT; Irritant/Hygroscopic/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥97.0% (HPLC); ≥98.5% (T); 98%; 98+%; 99%
• Grade: for catalysis
• Impurities: ≤0.02% water
• Antion Traces: bromide (Br-): ≤10 mg/kg; chloride (Cl-): ≤10 mg/kg; nitrate (NO3-): ≤10 mg/kg; phosphate (PO43-): ≤30 mg/kg; sulfate (SO42-): ≤10 mg/kg
• Empirical Formula (Hill Notation): C8H15F6N2P

DETAILS

Apollo Scientific Ltd - PC7732

Ionic Liquid

Sigma Aldrich - 70956

Other Notes
Ionic liquid employed in many environmentally friendly reactions1,2,3
Packaging
5, 50, 250 g in glass bottle

Sigma Aldrich - 18122

Packaging
5, 50 g in glass bottle
Application
Ionic Liquids for Catalysis

REFERENCES

• A copper-free Sonogashira coupling of terminal alkynes with aryl iodides, catalyzed by trans-Dichlorobis(triphenylphosphine)palladium(II), 10491, has been adapted to a microflow system for efficient catalyst recycling: Org. Lett., 4, 1691 (2002).
• Ionic liquid.
• For use in dihydroxylation of alkenes with Osmium(VIII) oxide, 12103, facilitating the reuse of the Os catalyst, see: Org. Lett., 4, 2197 (2002).
• Recyclable medium for oxidation of alcohols, catalyzed by TEMPO, A12733, and CuCl, to give aldehydes and ketones chemoselectively under mild conditions: Org. Lett., 4, 1507 (2002).
• Heck reactions with aryl halides can be carried out with controlled microwave heating: J. Org. Chem., 67, 6243 (2002).