1-Butyl-3-methylimidazolium bromide Chemical Properties

Melting point:

65-75°C

Density 

1.30 g/cm3(Temp: 25.1 °C)

storage temp. 

Store below +30°C.

form 

powder to lump

color 

White to Orange to Green

Water Solubility 

Miscible in water, methanol and dichloromethane. Immiscible in acetone, toluene, ethyl acetate and diethyl ether.

Sensitive 

Hygroscopic

InChI

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

InChIKey

KYCQOKLOSUBEJK-UHFFFAOYSA-M

SMILES

N1(CCCC)C=C[N+](C)=C1.[Br-]

CAS DataBase Reference

85100-77-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26-24/25

WGK Germany 

3

F 

10-21

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

1-Butyl-3-methylimidazolium bromide Usage And Synthesis

Chemical Properties

White crystals

Uses

It is an ionic liquid used in a Heck reaction. It is also used in assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure-property relationship modeling

Preparation

Preparation of 1-butyl-3-methylimidazolium bromide: A three-necked 50 mL round bottom flask was charged with N-methylimidazole (0.10 mol) followed by dropwise addition of 1-bromobutane (0.11 mol) at 70 ℃. After the addition was completed, the resulting mixture was stirred at 140 ℃ for 1.5 h. The combined organic layer was washed three times by ethyl acetate and vacuum-dried overnight at 70 ℃.

General Description

1-Butyl-3-methylimidazolium bromide is a neutral ionic liquid.

Synthesis

The general procedure for the synthesis of 1-butyl-3-methylimidazole bromide salts from N-butylimidazole and methyl bromide is as follows: all ligands (except 3) were synthesized by improving the method of Starikova et al [20]. The typical and general synthesis procedure is as follows: N-monosubstituted imidazole (0.1 mmol) was placed in a two-necked flask with anhydrous toluene and stirred until a homogeneous solution was formed. Subsequently, alkyl halides (0.3 mmol) were added slowly and dropwise under continuous stirring. After addition of the alkyl halide, the mixture was heated at 40°C for 24 hours with stirring. Upon completion of the reaction, the solvent was removed and the resulting ligand was dried under vacuum.2.2.3 1-Methyl-3-butylimidazolium bromide (4) as a colorless oil in a yield of 1.98 g (91% yield).IR (ATR, cm^-1 ): 3077, 2959, 1626, 1570, 1463, 1166, 1109, 752, 619, 460; ^1H NMR (400 MHz, CDCl3): δ 0.74 (3H, t, J=7.4 Hz, CH3), 1.18 (2H, m, CH2), 1.70 (2H, m, CH2), 3.92 (3H, s, NCH3), 4.14 (2H, t, J=6.7 Hz, NCH2), 7.42 (1H, s, NCH). 7.53 (1H, s, NCH), 10.03 ppm (1H, s, CH); ^13C NMR (100 MHz, CDCl3): δ 13.41 (CH3), 19.37 (CH2), 32.11 (CH2), 36.65 (NCH3), 49.72 (NCH2), 122.29, 123.83, 136.99 ppm; m/z (ESI) 139.4 (M^+ -Br^-); HRMS (ESI) calculated value C8H11BrN2, 139.12352 (M^+ -Br^-); measured value, 139.12327 (M^+ -Br^-).

References

[1] Journal of Molecular Catalysis A: Chemical, 2014, vol. 385, p. 98 - 105
[2] Chemical Communications, 2004, # 5, p. 590 - 591

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