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Merck

155071

Sigma-Aldrich

Azidotrimethylsilane

95%

Sinónimos:

Trimethylsilyl azide

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About This Item

Fórmula lineal:
(CH3)3SiN3
Número de CAS:
Peso molecular:
115.21
Beilstein/REAXYS Number:
1903730
EC Number:
MDL number:
UNSPSC Code:
12352103
eCl@ss:
39100709
PubChem Substance ID:
NACRES:
NA.23

assay

95%

form

liquid

refractive index

n20/D 1.414 (lit.)

bp

52-53 °C/175 mmHg (lit.)

density

0.868 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C[Si](C)(C)N=[N+]=[N-]

InChI

1S/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3

InChI key

SEDZOYHHAIAQIW-UHFFFAOYSA-N

General description

Azidotrimethylsilane (TMSN3) is a a colorless and stable organosilane reagent. It shows very slow decomposition at high temperatures. It is a very commonly used azide source and has been used in the synthesis of aminotriazole ligands. Azidotrimethylsilane can be easily synthesised by adding chlorotrimethylsilane dropwise to a stirred solution of NaN3 in diethylene glycol dimethyl ether.

Application

Azidotrimethylsilane can be used as:
  • A nitrogen precursor to prepare GaN nanowire via metal-organic chemical vapor deposition method.
  • An electrolyte additive in Li-O2 batteries. The addition of TMSN3 results in the formation of robust solid electrolyte interphase.
  • An efficient reagent in the synthesis of tetrazoles, fullerenyl azide, and α-azido oximes.
  • A silylating agent in the O-trimethyl silylation of alcohols and phenols.

pictograms

FlameSkull and crossbones

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

42.8 °F - closed cup

flash_point_c

6 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


Certificados de análisis (COA)

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Visite la Librería de documentos

Synthesis, 106-106 (1988)
Azidotrimethylsilane
Li, B. L.
Synlett, 23(10), 1554-1555 (2012)
Journal of the American Chemical Society, 116, 4501-4501 (1994)
Journal of the American Chemical Society, 115, 9347-9347 (1993)
Well-defined poly (oxazoline)-b-poly (acrylate) amphiphilic copolymers: From synthesis by polymer-polymer coupling to self-organization in water
Guillerm, Brieuc, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 51(5), 1118-1128 (2013)

Artículos

The chemistry of organoazides is exceedingly rich, since the azide functionality reacts with electrophiles, nucleophiles, and dipolarophiles, with or without the extrusion of dinitrogen. Common place transformation such as Staudinger reductions or ligations, Cu(I)-catalyzed Huisgen cycloadditions (of the “click” reaction family), Curtius or Schmidt rearrangents, nitrene reactions, or imine formation via aza-Wittig reactions all necessitate organoazide precursors or intermediates

Since the preparation of the first organic azide, phenyl azide, by Peter Griess in 1864 this energy-rich and versatile class of compounds has enjoyed considerable interest.

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