Imidazole-1-sulfonyl azide

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Imidazole-1-sulfonyl azide
Imidazole-1-sulfonyl azide.png
Identifiers
CAS number 952234-37-6 N
ChemSpider 21374920 YesY
Jmol-3D images Image 1
Properties
Molecular formula C3H3N5O2S
Molar mass 173.15 g mol−1
Appearance Colourless Liquid
Hazards
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)
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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 hydrogen sulfate salt.

Preparation[edit]

This compound is also available commercially [1]

Preparation of imidazole-1-sulfonyl azide.png

Reactions[edit]

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.[2] This reaction is effectively the reverse of the Staudinger reaction. Similarly, it is able to transfer the diazo group (=N2) under basic conditions.[2]

Safety[edit]

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.[2][3] 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.

References[edit]

  1. ^ van Delft, Floris. "SX-B1001". Synaffix. Retrieved 30 January 2014. 
  2. ^ a b c 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. 
  3. ^ 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.