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