Structural Formula Vector Image
Title: Butylmethylimidazolium
CAS Registry Number: 80432-08-2
CAS Name: 1-Butyl-3-methyl-1H-imidazolium
Additional Names: BMIM; C4mim
Molecular Formula: C8H15N2+
Literature References: Cation used in prepn of room temperature ionic liquids, q.v. Prepn of hexafluorophosphate and tetrafluoroborate: Y. Chauvin et al., Angew. Chem. Int. Ed. 34, 2698 (1995); and physical properties: P. A. Z. Suarez et al., J. Chim. Phys. 95, 1626 (1998). Prepn and properties of ionic liquids containing the imidazolium cation: J. G. Huddleston et al., Green Chem. 3, 156 (2001).
Derivative Type: Chloride
CAS Registry Number: 79917-90-1
Molecular Formula: C8H15ClN2
Molecular Weight: 174.67
Percent Composition: C 55.01%, H 8.66%, Cl 20.30%, N 16.04%
Literature References: Prepn: J. S. Wilkes et al., Inorg. Chem. 21, 1263 (1982).
Properties: Slightly yellow, may be crystalline at room temp depending on water content. mp 41° (dried) (Huddleston). Also reported as mp 65-69° (Wilkes). d25 1.08 (dried). Miscible with water.
Melting point: mp 41° (dried) (Huddleston); mp 65-69° (Wilkes)
Density: d25 1.08 (dried)
Derivative Type: Hexafluorophosphate
CAS Registry Number: 174501-64-5
Molecular Formula: C8H15F6N2P
Molecular Weight: 284.18
Percent Composition: C 33.81%, H 5.32%, F 40.11%, N 9.86%, P 10.90%
Literature References: Use as extraction medium: J. G. Huddleston et al., Chem. Commun. 16, 1765 (1998); as a solvent for alkylation reactions: M. J. Earle et al., ibid. 20, 2245 (1998). Use in environmentally benign manufacturing processes: L. A. Blanchard et al., Nature 339, 28 (1999). Microscopic solvent properties: S. N. Baker et al., Green Chem. 4, 165 (2002).
Properties: Viscous liquid, mp 4° (water equilibrated); 10° (dried). Glass transition temperature: -83° (water equilibrated), -80° (dried). Viscosity (25°): 397 cP (water equilibrated), 450 cP (dried). d25 1.35 (water equilibrated), 1.36 (dried). n25 1.409 (dried). Miscible with water. Imiscible with toluene, hexane, other non-polar solvents.
Melting point: mp 4° (water equilibrated); 10° (dried)
Index of refraction: n25 1.409 (dried)
Density: d25 1.35 (water equilibrated), 1.36 (dried)
Derivative Type: Tetrafluoroborate
CAS Registry Number: 174501-65-6
Molecular Formula: C8H15BF4N2
Molecular Weight: 226.02
Percent Composition: C 42.51%, H 6.69%, B 4.78%, F 33.62%, N 12.39%
Literature References: Use as a solvent for nucleophilic substitution reactions: D. W. Kim et al., J. Org. Chem. 68, 4281 (2003).
Properties: Viscous liquid. Glass transition temperature: -97° (dried). Viscosity (25°): 219 cP (dried). d25 1.12(dried). Miscible with water. Sol in methanol, ethanol. Insol in hydrocarbons.
Density: d25 1.12(dried)
Use: Solvent for organic reactions.

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