Physical properties
bp 43 °C/43 mmHg; IR νmax 2100 cm1;
1H NMR (CDCl3) δ = 0.12 (s, 9H), 2.75 (s, 2H); MS m/z
129, 73.
Uses
Trimethylsilylmethyl Azide is used in the amination of organometallic compounds; preparation of
heterocyclic compounds; precursor of azomethine ylide, reactant in Silylmethyl-Substituted Heterocumulenes and [3 + 2] Cycloaddition etc.
Preparation
Obtained in high yield by reaction of
sodium azide and (chloromethyl)trimethylsilane in DMF or
HMPA at 80°C.
Precautions
Trimethylsilylmethyl Azide is a useful, safe substitute for methyl azide, bp 20 °C, which is explosive. It is stable to temperatures of at least 120 °C and can be stored in a refrigerator for more than 6 months.
