Trimethylsilyl azide

Trimethylsilyl azide

Skeletal formula of Trimethylsilyl azide Ball-and-stick model of the trimethylsilyl azide molecule
Names
IUPAC name Azido(trimethyl)silane
Identifiers
CAS Number	4648-54-8 Y
Beilstein Reference	1903730
ChemSpider	70747 Y
EC Number	225-078-5
Jmol 3D model	Interactive image
PubChem	78378
InChI InChI=1S/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3 Y Key: SEDZOYHHAIAQIW-UHFFFAOYSA-N Y InChI=1/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3 Key: SEDZOYHHAIAQIW-UHFFFAOYAJ
SMILES [N-]=[N+]=N[Si](C)(C)C
Properties
Chemical formula	C3H9N3Si
Molar mass	115.21 g·mol−1
Appearance	clear liquid, colorless
Density	0.8763 g/cm3 (20 °C)
Melting point	−95 °C (−139 °F; 178 K)
Boiling point	52 to 53 °C (126 to 127 °F; 325 to 326 K) at 175 mmHg (92 to 95 °C at 760 mmHg)
Solubility in water	reacts to form dangerous hydrazoic acid
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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:

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 hydrazoic acid and therefore it must be stored free of moisture It has been used in the Oseltamivir total synthesis.

Safety

Trimethylsilyl azide is incompatible with moisture, strong oxidizing agents, and strong acids.