Trifluoromethanesulfonyl azide

Trifluoromethanesulfonyl azide or triflyl azide CF3SO2N3 is an organic azide used as a reagent in organic synthesis.

Preparation
Trifluoromethanesulfonyl azide is prepared by treating trifluoromethanesulfonic anhydride with sodium azide, traditionally in dichloromethane. However, the use of dichloromethane is avoided since it can generate highly explosive azido-chloromethane and diazidomethane. The reaction may also instead be conducted in toluene, acetonitrile, or pyridine.


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

An alternative route starts from imidazole-1-sulfonyl azide.

Reactions
Trifluoromethanesulfonyl azide generally converts amines to azides.