Sensitivities of Some Imidazole-1-sulfonyl Azide Salts

• Published in: Journal of organic chemistry 2012-02, Vol.77 (4), p.1760-1764
• Main Authors: Fischer, Niko, Goddard-Borger, Ethan D, Greiner, Robert, Klapötke, Thomas M, Skelton, Brian W, Stierstorfer, Jörg
• Format: Article
• Language: English
• Subjects: Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Organic chemistry; Preparations and properties
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo202264r

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.