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Imidazole-1-sulfonyl azide

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Imidazole-1-sulfonyl azide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H3N5O2S.ClH/c4-6-7-11(9,10)8-2-1-5-3-8;/h1-3H;1HKey: XYURSCOGYWBRDR-UHFFFAOYSA-N
  • InChI=1/C3H3N5O2S.ClH/c4-6-7-11(9,10)8-2-1-5-3-8;/h1-3H;1HKey: XYURSCOGYWBRDR-UHFFFAOYAJ
SMILES
  • Cl.O=S(=O)(N==)n1ccnc1
Properties
Chemical formula C3H3N5O2S
Molar mass 173.15 g·mol
Hazards
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). checkY verify (what is  ?) Infobox references
Chemical compound

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. A subsequent report noted that hydrazoic acid was formed upon hydrolysis, which did make the material sensitive.

References

  1. ^ 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.
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