Imidazole-1-sulfonyl azide hydrochloride, an inexpensive and effective diazotransfer
reagent, was recently found to be impact sensitive. To identify safer-to-handle forms
of this reagent, several different salts of imidazole-1-sulfonyl azide were prepared,
and their sensitivity to heat, impact, friction, and electrostatic discharge was quantitatively
determined. A number of these salts exhibited improved properties and can be considered
safer than the aforementioned hydrochloride. The solid-state structures of the chloride
and less sensitive hydrogen sulfate were determined by single-crystal X-ray diffraction
in an effort to provide some insight into the different properties of the materials.