Trimethylsilyl azide

Trimethylsilyl azide
Names
	IUPAC name Azido(trimethyl)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	clear liquid, colorless
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
R-phrases (outdated)	R11, R23, R24, R25, R29, R50, R51, R52, R53
S-phrases (outdated)	S16,S29,S36, S37,S45,S57,S8,
NFPA 704 (fire diamond)	3 4 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).

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)

Applications

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

Safety

Trimethylsilyl azide is incompatible with moisture, strong oxidizing agents, and strong acids. In 2014, a graduate student at the University of Minnesota was injured in an explosion that occurred in the synthesis of a large batch of trimethylsilyl azide.^[3]

References

^ L. Birkofer and P. Wegner (1988). "Trimethylsilyl azide". Organic Syntheses.; Collective Volume, 6, p. 1030
^ Jafarzadeh, Mohammad (2007). "Trimethylsilyl Azide (TMSN₃): A Versatile Reagent in Organic Synthesis". Synlett. 2007 (13): 2144–2145. doi:10.1055/s-2007-984895.
^ http://cenblog.org/the-safety-zone/2014/07/more-details-on-the-university-of-minnesota-explosion-and-response/

[1] L. Birkofer and P. Wegner (1988). "Trimethylsilyl azide". Organic Syntheses.; Collective Volume, 6, p. 1030

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

[3] ttp://cenblog.org/the-safety-zone/2014/07/more-details-on-the-university-of-minnesota-explosion-and-response/

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