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| ==Safety== | ==Safety== | ||
| 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 ], which made the material sensitive.<ref name = Goddard-Borger/><ref>{{cite journal | doi = 10.1021/jo202264r | journal = J. Org. Chem.}}</ref> | 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 ], which made the material sensitive.<ref name = Goddard-Borger/><ref>{{cite journal | doi = 10.1021/jo202264r | journal = J. Org. Chem. | title = Sensitivities of Some Imidazole-1-sulfonyl Azide Salts | year = 2012 | last1 = Fischer | first1 = Niko | last2 = Goddard-Borger | first2 = Ethan D. | last3 = Greiner | first3 = Robert | last4 = Klapötke | first4 = Thomas M. | last5 = Skelton | first5 = Brian W. | last6 = Stierstorfer | first6 = Jörg | volume = 77 | issue = 4 | pages = 1760}}</ref> | ||
| ==References== | ==References== | ||
Revision as of 23:48, 18 February 2012
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| Properties | |
| Chemical formula | C3H3N5O2S |
| Molar mass | 173.15 g·mol |
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| Occupational safety and health (OHS/OSH): | |
| Main hazards | Potentially explosive |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
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Infobox references
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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.
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.
Reactions
Like trifluoromethanesulfonyl azide, this compound generally converts primary amines or ammonium salts to azides. 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.
Safety
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.
References
- ^ 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. 13 (9): 2514. doi:10.1021/ol2007555.{{cite journal}}:|format=requires|url=(help) - 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.