Imidazole-1-sulfonyl azide

It is an explosive colorless liquid, but some of its organic-soluble salts can be safely handled and stored as a solid.

The hydrochloride salt of this compound is also available commercially, but can degrade to release explosive byproducts.

[3] Subsequent reports noted that the hydrochloride salt is hygroscopic, and upon prolonged storage was hydrolyzed to produce hydrazoic acid, which made the material sensitive.

[4] Recent studies have shown the hydrogen sulfate salt to be significantly less hazardous to handle with decomposition temperature of 131 °C, insensitivity to impact, and low electrostatic discharge and friction sensitivities.

[3] Further improvements have led to its synthesis with increased safety, making the hydrogen sulfate salt a relatively safe diazo-transfer reagent to both synthesize and handle.

Space-filling model of the imidazole-1-sulfonyl azide molecule
Space-filling model of the imidazole-1-sulfonyl azide molecule