Trifluoromethanesulfonyl azide

Trifluoromethanesulfonyl azide
IUPAC name

N-diazo-1,1,1-trifluoro-methanesulfonamide
Identifiers
CAS number 3855-45-6
PubChem 10986786
ChemSpider 9161983 Y
Jmol-3D images Image 1
Properties
Molecular formula CF3N3O2S
Molar mass 175.09 g mol−1
Solubility in water insoluble[1]
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

Contents

Preparation

Trifluoromethanesulfonyl azide is not commercially available. It is prepared before use by reacting trifluoromethanesulfonic anhydride with sodium azide, traditionally in dichloromethane.[1] The reaction may also be carried out in acetonitrile or pyridine.[2]

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.[3]

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.[1]

See also

References

  1. ^ a b c 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. 
  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.