Sensitivities of Some Imidazole-1-sulfonyl Azide Salts

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.