Trimethylsilyl azide

Trimethylsilyl azide

IUPAC name Azido(trimethyl)silane
Identifiers
CAS number	4648-54-8^Y
PubChem	78378
ChemSpider	70747^Y
EC number	225-078-5
Beilstein Reference	1903730
Jmol-3D images	Image 1
SMILES [N-]=[N+]=N[Si](C)(C)C
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
Properties
Molecular formula	C₃H₉N₃Si
Molar mass	115.21 g mol⁻¹
Appearance	clear liquid, color less
Density	0.8763 g/cm3 (20 C)
Melting point	-95°C
Boiling point	52-53°C at 175mmHg; 92-95°C at 760mmHg
Hazards
R-phrases	R11, R23, R24, R25, R29, R50, R51, R52, R53
S-phrases	S16,S29,S36, S37,S45,S57,S8,
NFPA 704	3 4 0
Flash point	6 °C
Autoignition temperature	> 300 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Trimethylsilyl azide ((CH₃)₃SiN₃) is a chemical compound used as a reagent in organic chemistry.

Preparation

Trimethylsilyl azide is commercially available. It may be prepared by the reaction of trimethylsilyl chloride and sodium azide:^[1]

TMSCl + NaN₃ → TMSN₃ + NaCl (TMS = (CH₃)₃Si)

It is considered a safer replacement for hydrazoic acid in many reactions. It will however over time hydrolyze to hydrogen azide and therefore it must be stored free of moisture ^[2] It has been used in the Oseltamivir total synthesis.

Trimethylsilyl azide is incompatible with moisture, strong oxidizing agents, and strong acids.

^ L. Birkofer and P. Wegner (1988), "Trimethylsilyl azide", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p1030 ; Coll. Vol. 6: 1030
^ Jafarzadeh, Mohammad (2007). "Trimethylsilyl Azide (TMSN₃): A Versatile Reagent in Organic Synthesis". Synlett 2007 (13): 2144. doi:10.1055/s-2007-984895.