Chemistry:Trimethylsilyl azide

Trimethylsilyl azide

Names
Preferred IUPAC name Azidotri(methyl)silane
Identifiers
CAS Number	4648-54-8 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1903730
ChemSpider	70747 Y
EC Number	225-078-5
PubChem CID	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	115.211 g·mol−1
Appearance	colorless liquid
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
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H301, H311, H331, H410
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+310, P302+352, P303+361+353, P304+340, P311, P312, P321, P322, P330, P361, P363, P370+378, P391
NFPA 704 (fire diamond)	3 4 0
Flash point	6 °C (43 °F; 279 K)
Autoignition temperature	> 300 °C (572 °F; 573 K)
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

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Trimethylsilyl azide is the organosilicon compound with the formula (CH
3)
3SiN
3. A colorless liquid, it is a reagent in organic chemistry, serving as the equivalent of hydrazoic acid.

Preparation

Trimethylsilyl azide is commercially available. It may be prepared by the reaction of trimethylsilyl chloride and sodium azide:

(CH
3)
3Si–Cl + NaN
3 → (CH
3)
3Si–N
3 + NaCl

Reactions

The compound hydrolyzes to hydrazoic acid:

(CH
3)
3SiN
3 + H
2O → (CH
3)
3SiOH + HN
3

The compound adds to ketones and aldehydes to give the siloxy azides and subsequently tetrazoles:

(CH
3)
3SiN
3 + R
2CO → R
2C(N
3)OSi(CH
3)
3

It ring-opens epoxides to give azido alcohols.

It has been used in the Oseltamivir total synthesis.

Safety

Trimethylsilyl azide is incompatible with moisture, strong oxidizing agents, and strong acids. Azides are often explosive, as illustrated by their use in air bags.