2-Chloro-1H-imidazole

Chemical Properties

2-Chloro-1H-imidazole is an imidazole compound with the appearance of white to off-white powder to crystal, molecular weight 102.52, melting point 166.0 ~ 170.0 °C, it is sensitive to heat, and is usually stored at 2-8°C. It can be used as an antimicrobial agent in the manufacture of imidazoles.

Uses

2-Chloro-1H-imidazole can be used as an organic reaction reagent for the study of halogenated imidazoles. It is mainly used for chemical and laboratory research use.

Uses

2-Chloroimidazole is used in pharmaceuticals, drug candidates, ligands for transition metal catalysts and other molecular functional materials.

Definition

ChEBI: An imidazole compound having a chloro substituent at the 2-position.

Synthesis Reference(s)

The Journal of Organic Chemistry, 63, p. 12, 1998 DOI: 10.1021/jo970355+

Synthesis

The general procedure for the synthesis of 2-chloroimidazole from 1-(diethoxymethyl)imidazole is as follows: with reference to Example 9, 2-chloroimidazole was prepared as follows: N-(diethoxymethyl)imidazole (50.0 g) was dissolved in tetrahydrofuran (200 ml), and a n-hexane solution of 2.6 M n-butyllithium (120 ml) was added slowly and dropwise to this solution. The addition of tetrahydrofuran solution (100 ml) of hexachloroethane (73.9 g) was continued dropwise at -35°C. The reaction mixture was kept at the same temperature for 5 min, then warmed up to -20°C and 6N hydrochloric acid (100 ml) was added, after which it was restored to room temperature and left to stand for 5 min. The aqueous layer was separated and the organic layer was extracted with 1N hydrochloric acid, the extract was combined with the aqueous layer and washed with ether. This was followed by neutralization with 6N aqueous sodium hydroxide and extraction with ethyl acetate. The organic layer was separated, dried with anhydrous magnesium sulfate and the solvent was removed by distillation to give the crude product. The crude product was ground with dichloromethane to give finally 2-chloroimidazole (26.0 g, yield: 85.0%) as a light brown solid.1H-NMR (CDCl3) δ (ppm): 10.64 (1H, bs), 7.05 (1H, s).

References

[1] Patent: EP1553088, 2005, A1. Location in patent: Page/Page column 52