Trimethylsilyl azide

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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).
checkY verify (what is checkY☒N ?)

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

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

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

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

  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.
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