Trimethylsilyl azide

Trimethylsilyl azide
Names
	Preferred IUPAC name Azidotri(methyl)silane
Identifiers
CAS Number	4648-54-8 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1903730
ChemSpider	70747 ;
ECHA InfoCard	100.022.798
EC Number	225-078-5;
PubChem CID	78378;
CompTox Dashboard (EPA)	DTXSID3063542 ;
	InChI InChI=1S/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3 Key: SEDZOYHHAIAQIW-UHFFFAOYSA-N ; 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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H301, H311, H331, H410
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P311, P312, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)	4 3 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). verify (what is ?) Infobox references

Trimethylsilyl azide is the organosilicon compound with the formula (CH₃)₃SiN₃. A colorless liquid, it is a reagent in organic chemistry, serving as the equivalent of hydrazoic acid.^[1]

Preparation[edit]

Trimethylsilyl azide is commercially available. It may be prepared by the reaction of trimethylsilyl chloride and sodium azide:^[2]

(CH₃)₃Si−Cl + NaN₃ → (CH₃)₃Si−N₃ + NaCl

Reactions[edit]

The compound hydrolyzes to hydrazoic acid:^[3]

(CH₃)₃SiN₃ + H₂O → (CH₃)₃SiOH + HN₃

The compound adds to ketones and aldehydes to give the siloxy azides and subsequently tetrazoles:^[1]

(CH₃)₃SiN₃ + R₂CO → R₂C(N₃)OSi(CH₃)₃

It ring-opens epoxides to give azido alcohols.

It has been used in the Oseltamivir total synthesis.

Safety[edit]

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

References[edit]

^ ^a ^b Nishiyama, Kozaburo; Wang, Cheng; Lebel, Hélène (2016). "Azidotrimethylsilane". Encyclopedia of Reagents for Organic Synthesis. pp. 1–16. doi:10.1002/047084289X.ra117.pub3. ISBN 9780470842898.
^ L. Birkofer and P. Wegner (1970). "Trimethylsilyl azide". Organic Syntheses. 50: 107. doi:10.15227/orgsyn.050.0107.
^ Jafarzadeh, Mohammad (2007). "Trimethylsilyl Azide (TMSN₃): A Versatile Reagent in Organic Synthesis". Synlett. 2007 (13): 2144–2145. doi:10.1055/s-2007-984895.

[EROS-1] Nishiyama, Kozaburo; Wang, Cheng; Lebel, Hélène (2016). "Azidotrimethylsilane". Encyclopedia of Reagents for Organic Synthesis. pp. 1–16. doi:10.1002/047084289X.ra117.pub3. ISBN 9780470842898.

[2] L. Birkofer and P. Wegner (1970). "Trimethylsilyl azide". Organic Syntheses. 50: 107. doi:10.15227/orgsyn.050.0107.

[3] Jafarzadeh, Mohammad (2007). "Trimethylsilyl Azide (TMSN₃): A Versatile Reagent in Organic Synthesis". Synlett. 2007 (13): 2144–2145. doi:10.1055/s-2007-984895.

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