Imidazole-1-sulfonyl azide

Imidazole-1-sulfonyl azide
Identifiers
CAS number 952234-37-6
ChemSpider 21374920 Y
Jmol-3D images Image 1
Properties
Molecular formula C3H3N5O2S
Molar mass 173.15 g mol−1
Hazards
Main hazards Potentially explosive
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 hydrochloride salt.

Contents

Preparation

This compound is not readily available commercially. It may be prepared by reacting sulfuryl chloride with sodium azide in acetonitrile, followed by the addition of excess imidazole. The hydrochloride salt may be obtained by precipitating with an ethanol solution of HCl.[1]

Reactions

Like trifluoromethanesulfonyl azide, this compound generally converts primary amines or ammonium salts to azides.[1] This reaction is effectively the reverse of the Staudinger reaction. Similarly, it is able to transfer the diazo group (=N2) when catalyzed by copper(II), nickel(II), zinc(II), and cobalt(II) salts.[1]

Safety

As with all organic azides, this compound is potentially explosive. Impact tests, vigorous grinding, and prolonged heating at 80 °C of the hydrochloride salt did not result in any explosive reaction, though heating above 150 °C resulted in violent decomposition.[1]

References

  1. ^ a b c d 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.