Trimethylsilyl azide

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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]

Trimethylsilyl azide
Skeletal formula of Trimethylsilyl azide
Ball-and-stick model of the trimethylsilyl azide molecule
Names
Preferred IUPAC name
Azidotri(methyl)silane
Identifiers
3D model (JSmol)
1903730
ChemSpider
ECHA InfoCard 100.022.798 Edit this at Wikidata
EC Number
  • 225-078-5
  • InChI=1S/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3 checkY
    Key: SEDZOYHHAIAQIW-UHFFFAOYSA-N checkY
  • InChI=1/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3
    Key: SEDZOYHHAIAQIW-UHFFFAOYAJ
  • [N-]=[N+]=N[Si](C)(C)C
Properties
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)
reacts to form dangerous hydrazoic acid
Hazards
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS09: Environmental hazard
Danger
H225, H301, H311, H331, H410
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)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
3
0
Flash point 6 °C (43 °F; 279 K)
> 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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Preparation

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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

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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

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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

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  1. ^ 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.
  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.