Trimethylsilyl azide
Names
Preferred IUPAC name
Identifiers
1903730
ChemSpider
ECHA InfoCard 100.022.798
EC Number
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
Properties
C 3 H 9 N 3 Si
Molar mass
−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
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
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).
Chemical compound
Trimethylsilyl azide is the organosilicon compound with the formula (CH3 )3 SiN3 . 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 )3 Si−Cl + NaN3 → (CH3 )3 Si−N3 + NaCl
Reactions
The compound hydrolyzes to hydrazoic acid :[ 3]
(CH3 )3 SiN3 + H2 O → (CH3 )3 SiOH + HN3 The compound adds to ketones and aldehydes to give the siloxy azides and subsequently tetrazoles:[ 1]
(CH3 )3 SiN3 + R2 CO → R2 C(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
