Trimethylsilyl azide
| |
| Names | |
|---|---|
| IUPAC name
Azido(trimethyl)silane
| |
| Identifiers | |
3D model (JSmol)
|
|
| ECHA InfoCard | 100.022.798 |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| Properties | |
| C3H9N3Si | |
| Molar mass | 115.211 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Trimethylsilyl azide ((CH3)3SiN3) is a chemical compound used as a reagent in organic chemistry.
Preparation
Trimethylsilyl azide is commercially available. It may be prepared by the reaction of trimethylsilyl chloride and sodium azide:[1]
- TMSCl + NaN3 → TMSN3 + NaCl (TMS = (CH3)3Si)
Applications
It is considered a safer replacement for hydrazoic acid in many reactions. It will however over time hydrolyze to hydrogen azide and therefore it must be stored free of moisture [2] It has been used in the Oseltamivir total synthesis.
References
- ^ L. Birkofer and P. Wegner (1988). "Trimethylsilyl azide". Organic Syntheses; Collected Volumes, vol. 6, p. 1030.
- ^ Jafarzadeh, Mohammad (2007). "Trimethylsilyl Azide (TMSN3): A Versatile Reagent in Organic Synthesis". Synlett. 2007: 2144. doi:10.1055/s-2007-984895.