Imidazole-1-sulfonyl azide

Imidazole-1-sulfonyl azide

Identifiers
CAS Number	952234-37-6 N
ChemSpider	21374920 Y
Jmol interactive 3D	Image
InChI InChI=1S/C3H3N5O2S.ClH/c4-6-7-11(9,10)8-2-1-5-3-8;/h1-3H;1H Y Key: XYURSCOGYWBRDR-UHFFFAOYSA-N Y InChI=1/C3H3N5O2S.ClH/c4-6-7-11(9,10)8-2-1-5-3-8;/h1-3H;1H Key: XYURSCOGYWBRDR-UHFFFAOYAJ
SMILES Cl.O=S(=O)(N=[N+]=[N-])n1ccnc1
Properties
Chemical formula	C3H3N5O2S
Molar mass	173.15 g·mol−1
Appearance	Colourless Liquid
Hazards
Main hazards	Potentially explosive, Harmful
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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

This compound is also available commercially ^[1]

Reactions

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

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

1. ↑ van Delft, Floris. "SX-B1001". Synaffix. Retrieved 30 January 2014. 
2. 1 2 3 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)|format= requires |url= (help) 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.