1-butyl-3-methyl-1H-imidazol-3-ium; tetrafluoroboranuide

• ChemBase ID: 140026
• Molecular Formular: C8H15BF4N2
• Molecular Mass: 226.0227128
• Monoisotopic Mass: 226.12644177
• SMILES: [B-](F)(F)(F)F.CCCCn1cc[n+](c1)C
• Canonical SMILES: F[B-](F)(F)F.CCCCn1cc[n+](c1)C
• InChI: InChI=1S/C8H15N2.BF4/c1-3-4-5-10-7-6-9(2)8-10;2-1(3,4)5/h6-8H,3-5H2,1-2H3;/q+1;-1
• InChIKey: LSBXQLQATZTAPE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-butyl-3-methyl-1H-imidazol-3-ium; tetrafluoroboranuide
• IUPAC Traditional name: 1-butyl-3-methylimidazolium tetrafluoroborate
• Synonyms: 1-n-Butyl-3-methylimidazolium tetrafluoroborate; BMIMBF4; Basionics® EE 04; 1-Butyl-3-methylimidazolium tetrafluoroborate; 1-正-丁基-3-甲基咪唑鎓 四氟硼酸盐; 1-丁基-3-甲基咪唑鎓四氟硼酸盐

Database IDs

• CAS Number: 174501-65-6
• EC Number: 000-000-0
• MDL Number: MFCD03095449
• PubChem SID: 24864803; 162234271; 24889490
• PubChem CID: 2734178

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

• Flash Point: 288 °C; 550.4 °F; None
• Density: 1.21 g/mL at 20 °C(lit.); 1.210
• Refractive Index: 1.4220; n20/D 1.52

Safety Information

• European Hazard Symbols: Nature polluting (N); Toxic (T); Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 25-36/38-51/53; 36/37/38
• Safety Statements: 26-37; 26-45-61
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H411; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P273-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥97.0% (HPLC); ≥98%; ≥98.5% (HPLC); 98+%
• Grade: BASF quality; for catalysis
• Impurities: ≤0.05% water; ≤0.5% water
• Antion Traces: bromide (Br-): ≤25 mg/kg; chloride (Cl-): ≤25 mg/kg; nitrate (NO3-): ≤25 mg/kg; phosphate (PO43-): ≤10 mg/kg; sulfate (SO42-): ≤25 mg/kg
• Empirical Formula (Hill Notation): C8H15BF4N2

DETAILS

Sigma Aldrich - 91508

Other Notes
Ionic liquid used in many reactions, e.g. hydrogenations1; asymmetric hydrogenations proceed in higher enantioselectivity than in homogeneous phase2; Suzuki cross-coupling at ambient temperature3
Packaging
5, 50, 250 g in glass bottle

Sigma Aldrich - 711748

General description
produced by Sigma-Aldrich, production and use of trademark licensed from BASF
Packaging
1 kg in glass bottle
100 g in glass bottle
Legal Information
Basionics is a registered trademark of BASF SE

Sigma Aldrich - 39931

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

REFERENCES

• Ionic liquid.
• Effective medium for fluorination of alkyl halides with KF: J. Am. Chem. Soc., 124, 10278 (2002).
• The Suzuki coupling of arylboronic acids with aryl bromides gave improved yields with reduced catalyst concentrations (Tetrakis(triphenylphosphine)palladium(0), 10548) with this reaction medium: Chem. Commun., 1249 (2000). Acceleration of Suzuki coupling of polymer-supported 4-iodophenol with arylboronic acids has also been observed: Org. Lett., 4, 3071 (2002).