Misplaced Pages

Imidazole-1-sulfonyl azide

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

This is an old revision of this page, as edited by Citation bot (talk | contribs) at 23:48, 18 February 2012 (Add: title, year, last1, first1, last2, first2, last3, first3, last4, first4, last5, first5, last6, first6, volume, issue, pages. Tweak: title, year, volume, issue, pages. | Rifleman 82). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 23:48, 18 February 2012 by Citation bot (talk | contribs) (Add: title, year, last1, first1, last2, first2, last3, first3, last4, first4, last5, first5, last6, first6, volume, issue, pages. Tweak: title, year, volume, issue, pages. | Rifleman 82)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
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. Subsequent reports noted that upon storage, the hydrochloride salt hydrolyzed to produce hydrazoic acid, which made 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. {{cite journal}}: |format= requires |url= (help)
  2. 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.
Categories: