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Trifluoromethanesulfonyl azide

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Trifluoromethanesulfonyl azide
Names
IUPAC name N-diazo-1,1,1-trifluoro-methanesulfonamide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/CF3N3O2S/c2-1(3,4)10(8,9)7-6-5Key: NQPHMXWPDCSHTE-UHFFFAOYSA-N
  • InChI=1/CF3N3O2S/c2-1(3,4)10(8,9)7-6-5Key: NQPHMXWPDCSHTE-UHFFFAOYAT
SMILES
  • FC(F)(F)S(=O)(=O)N==
Properties
Chemical formula CF3N3O2S
Molar mass 175.09 g·mol
Solubility in water insoluble
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

Trifluoromethanesulfonyl azide or triflyl azide is an organic azide used as a reagent in organic synthesis.

Preparation

Trifluoromethanesulfonyl azide is not commercially available. It is prepared before use by reacting trifluoromethanesulfonic anhydride with sodium azide, traditionally in dichloromethane. The reaction may also be carried out in acetonitrile or pyridine.

Tf2O + NaN3 → TfN3 + NaOTf (Tf = CF3SO2)

The trifluoromethanesulfonic anhydride starting material is rather expensive, and the product is explosive, and does not store well. As a result, imidazole-1-sulfonyl azide has been developed as an alternative.

Reactions

Trifluoromethanesulfonyl azide generally converts amines to azides. Trifluoromethanesulfonyl azide may be formed in situ from trifluoromethanesulfonic anhydride and sodium azide; it reacts with the amine present in a one-pot reaction.

See also


References

  1. ^ C. J. Cavender and V. J. Shiner (1972). "Trifluoromethanesulfonyl azide. Its reaction with alkyl amines to form alkyl azides". The Journal of Organic Chemistry. 37 (22): 3567–3569. doi:10.1021/jo00795a052.
  2. R.-B. Yan, F. Yang, Y. Wu, L.-H. Zhang and X.-S. Ye (2005). "An efficient and improved procedure for preparation of triflyl azide and application in catalytic diazotransfer reaction". Tetrahedron Letters. 46 (52): 8993–8995. doi:10.1016/j.tetlet.2005.10.103.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.
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