2-BROMO-4-METHYL-1H-IMIDAZOLE Chemical Properties

Melting point:

110-114

Boiling point:

280.7±33.0 °C(Predicted)

Density 

1.723±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

powder

pka

11.66±0.10(Predicted)

color 

Yellow

InChI

InChI=1S/C4H5BrN2/c1-3-2-6-4(5)7-3/h2H,1H3,(H,6,7)

InChIKey

AYQISCMXBQVMSY-UHFFFAOYSA-N

SMILES

C1(Br)NC(C)=CN=1

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2933299090

2-BROMO-4-METHYL-1H-IMIDAZOLE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-bromo-4-methyl-1H-imidazole from 2,5-dibromo-4-methylimidazole: [Example 6]; At room temperature, 23.9 g (100.0 mmol) of 2,5-dibromo-4-methylimidazole, 29.4 g (300.0 mmol) of cyclohexanone, and 23.9 g (259.4 mmol) of toluene were mixed, and during stirring, slow addition of 22.5 g (150.0 mmol) of sodium iodide to prepare the reaction solution. The reaction solution was stirred at 105 °C for 12 h under nitrogen protection, followed by cooling in an ice bath and continued stirring for 1 h. The reaction solution was analyzed by HPLC. Analysis of the reaction solution by HPLC confirmed the formation of 13.7 g (82.3 mmol, conversion: 85.3%) of 2-bromo-4-methyl-1H-imidazole. The reaction solution was concentrated under reduced pressure and purified by silica gel column chromatography (eluent: ethyl acetate/hexane mixed system). The product-containing fractions were collected, and after evaporation to remove volatile components, 2-bromo-4-methyl-1H-imidazole crystals were obtained in a yield of 12.6 g (yield: 78.1%). The obtained crystals were further confirmed to be 2-bromo-4-methyl-1H-imidazole by comparing the NMR spectrum of the product with that of the standard sample.

References

[1] Patent: EP2141151, 2010, A1. Location in patent: Page/Page column 7

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