Nucleophilic displacements of chlorine from 2-trichloromethylbenzimidazole by water, alcohols, phenols, and their sulphur analogues are described. The special reactivity of the trichloromethyl group in this compound is compared with that of the trichloromethyl group in non-activated positions. The Friedel–Crafts reaction of 2-trichloromethylbenzimidazole with benzene is reported.