| Identification | More | [Name]
2-Bromo-1-methyl-1H-imidazole | [CAS]
16681-59-7 | [Synonyms]
2-BROMO-1-METHYL-1H-IMIDAZOLE
2-BROMO-1-METHYLIMIDAZOLE
2-Bromo-1-methyl-1H-imidazole 97%
1-METHYL-2-BROMOIMIDAZOLE
3-METHYL-3-PHENYLBUTANOIC ACID
1-Methyl-2-bromo-1H-imidazole | [Molecular Formula]
C4H5BrN2 | [MDL Number]
MFCD02179525 | [Molecular Weight]
161 | [MOL File]
16681-59-7.mol |
| Chemical Properties | Back Directory | [Boiling point ]
172 °C (lit.) | [density ]
1.649 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.5440(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Inert atmosphere,Store in freezer, under -20°C | [form ]
Liquid | [pka]
3.83±0.25(Predicted) | [color ]
Clear colorless to pale yellow to pink | [InChI]
InChI=1S/C4H5BrN2/c1-7-3-2-6-4(7)5/h2-3H,1H3 | [InChIKey]
BANOTGHIHYMTDL-UHFFFAOYSA-N | [SMILES]
C1(Br)N(C)C=CN=1 | [CAS DataBase Reference]
16681-59-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R38:Irritating to the skin.
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29332990 |
| Hazard Information | Back Directory | [Uses]
2-Bromo-1-methylimidazole is used in in pharmaceuticals, drug candidates, ligands for transition metal catalysts and other molecular functional materials. | [Synthesis]
General procedure for the synthesis of 2-bromo-1-methyl-1H-imidazole from N-methylimidazole: 1-methylimidazole (1 mmol, 82.1 mg) and carbon tetrabromide (1.1 mmol, 364.8 mg) were added to a 10 mL round bottom flask. Subsequently, 5 mL of N,N-dimethylformamide and sodium tert-butoxide (4.0 mmol, 384.4 mg) were added and the reaction was stirred at room temperature for 3 h, during which the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was poured into water and extracted with dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate and the dichloromethane was removed by rotary evaporator to give the crude product. The crude product was purified by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate (v/v=10:1) as the eluent, and finally 2-bromo-1-methyl-1H-imidazole (reddish brown liquid, 101.4 mg, 63% yield) was obtained. | [References]
[1] Chemical Communications, 2013, vol. 49, # 37, p. 3875 - 3877
[2] Australian Journal of Chemistry, 1999, vol. 52, # 3, p. 159 - 165
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 6, p. 886 - 890
[4] Patent: CN107501023, 2017, A. Location in patent: Paragraph 0055; 0056
[5] Polish Journal of Chemistry, 1981, vol. 55, # 7/8, p. 1659 - 1665 |
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