|Jmol-3D images||Image 1|
|Molar mass||173.15 g mol−1|
|Main hazards||Potentially explosive, Harmful|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Imidazole-1-sulfonyl azide is an organic azide compound that can be used as an alternative to trifluoromethanesulfonyl azide. It is a colorless liquid; it may also be used as a better-handled hydrogen sulfate salt.
This compound is also available commercially 
Like trifluoromethanesulfonyl azide, this compound generally converts primary amines or ammonium salts to azides when catalyzed by copper(II), nickel(II), zinc(II), and cobalt(II) salts. This reaction is effectively the reverse of the Staudinger reaction. Similarly, it is able to transfer the diazo group (=N2) under basic conditions.
As with all organic azides, this compound is potentially explosive. The hydrochloride salt was initially reported to be insensitive to impact, vigorous grinding, and prolonged heating at 80 °C, although heating above 150 °C resulted in violent decomposition. Subsequent reports noted that upon storage, the hydrochloride salt hydrolyzed to produce hydrazoic acid, which made the material sensitive. Note: We synthesized this and had 20 g explode when unattended in a vacuum oven when it was in a dry state, please be careful if you plan to use/make this chemical.
- van Delft, Floris. "SX-B1001". Synaffix. Retrieved 30 January 2014.
- E. D. Goddard-Borger and R. V. Stick (2007). "An Efficient, Inexpensive, and Shelf-Stable Diazotransfer Reagent: Imidazole-1-sulfonyl Azide Hydrochloride". Organic Letters 9 (19): 3797–3800. doi:10.1021/ol701581g. PMID 17713918.
E. D. Goddard-Borger and R. V. Stick (2011). "An Efficient, Inexpensive, and Shelf-Stable Diazotransfer Reagent: Imidazole-1-sulfonyl Azide Hydrochloride". Organic Letters (Addition/Correction ) 13 (9): 2514. doi:10.1021/ol2007555.
- Fischer, Niko; Goddard-Borger, Ethan D.; Greiner, Robert; Klapötke, Thomas M.; Skelton, Brian W.; Stierstorfer, Jörg (2012). "Sensitivities of Some Imidazole-1-sulfonyl Azide Salts". J. Org. Chem. 77 (4): 1760. doi:10.1021/jo202264r.