2-Bromo-1-methyl-1H-imidazole
-
2-Bromo-1-methyl-1H-imidazole
structure -
-
CAS No:
16681-59-7
-
Formula:
C4H5BrN2
-
Chemical Name:
2-Bromo-1-methyl-1H-imidazole
-
Synonyms:
1H-Imidazole,2-bromo-1-methyl-;Imidazole,2-bromo-1-methyl-;2-Bromo-1-methyl-1H-imidazole;2-Bromo-1-methylimidazole;2-Bromo-N-methylimidazole;151223-71-1
-
CAS No:
Characteristics
17.8
0.2
Clear colorless to pale yellow to pink Liquid
1.649 g/mL at 25 °C(lit.)
115 °C @ Press: 20 Torr
>230 °F
n 20/D 1.5440(lit.)
Safety Information
NONH for all modes of transport
3
22-38-41
26
Xn,Xi
Irritant
P280-P305 + P351 + P338
H302-H315-H318
|Danger|H302 (97.62%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P362, and P501|Aggregated GHS information provided by 42 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-Bromo-1-methyl-1H-imidazole Use and Manufacturing
1-methylimidazole (1 mmol, 82.1 mg), Carbon tetrabromide (1.1 mmol, 364.8 mg) was placed in a 10 mL round bottom flask.Added 5 mL of N, N-dimethylformamide and sodium tert-butoxide (4.0 mmol, 384.4 mg).Stir at room temperature for 3 hours, TLC monitored the endpoint of the reaction. The mixture is poured into water and extracted with dichloromethane. The organic phase is collected, dried, and the dichloromethane is removed by rotary evaporation.Crude product. The crude product was subjected to silica gel column chromatography with petroleum ether and ethyl acetate as eluents (volume ratio = 10:1) to obtain 2-Bromo-1-methylimidazole (red-brown liquid, 101.4 mg, yield 63percent).Step 1 To a solution of 1-H-imidazole (8.20 g, 100 mmol) in dry THF (210 mL) at -78 C. was added n-butyllithium (1.6M in hexane, 75 mL, 120 mmol) dropwise. The solution was gradually warmed up to room temperature and further stirred for 2 h. The mixture was then cooled to -78 C., and tetrabromomethane (33.2 g, 100 mmol) in 30 mL of dry THF was added dropwise. After the addition, the mixture continued to stir for 15 min and was quenched by water. The mixture was extracted with ether and purified by a silica gel column with ethyl acetate as eluent. Distillation of the product gave N-methyl-2-bromoimidazole as a colorless oil (7.40 g, 46% yield), characterized by 1H-NMR and MS.
Computed Properties
Molecular Weight:161.00
XLogP3:0.2
Hydrogen Bond Acceptor Count:1
Exact Mass:159.96361
Monoisotopic Mass:159.96361
Topological Polar Surface Area:17.8
Heavy Atom Count:7
Complexity:66.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
