| Identification | More | [Name]
1-Butyl-3-methylimidazolium bromide | [CAS]
85100-77-2 | [Synonyms]
1-BUTYL-3-METHYLIMIDAZOLIUM BROMIDE
1-N-BUTYL-3-METHYLIMIDAZOLIUM BROMIDE
BMIMBR
1-Butyl-3-methyl-1H-imidazolium bromide
1-Butyl-3-methylimidazolium bromide ,99% | [EINECS(EC#)]
617-674-2 | [Molecular Formula]
C8H15BrN2 | [MDL Number]
MFCD03427611 | [Molecular Weight]
219.12 | [MOL File]
85100-77-2.mol |
| Chemical Properties | Back Directory | [Appearance]
White crystals | [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 | [Detection Methods]
NMR,HPLC | [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) | [Storage Precautions]
Store under nitrogen |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [F ]
10-21 | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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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