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Chemical compound From Wikipedia, the free encyclopedia
Trifluoromethanesulfonyl azide or triflyl azide CF3SO2N3 is an organic azide used as a reagent in organic synthesis.[2]
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Names | |||
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Preferred IUPAC name
Trifluoromethanesulfonyl azide | |||
Identifiers | |||
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Properties | |||
CF3SO2N3 | |||
Molar mass | 175.09 g·mol−1 | ||
Melting point | 80-81 °C | ||
insoluble[1] | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trifluoromethanesulfonyl azide is prepared by treating trifluoromethanesulfonic anhydride with sodium azide, traditionally in dichloromethane.[1] 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,[3] acetonitrile, or pyridine.[4]
An alternative route starts from imidazole-1-sulfonyl azide.[5]
Trifluoromethanesulfonyl azide generally converts amines to azides.
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