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Merck
CN

155071

Azidotrimethylsilane

95%

Synonym(s):

Trimethylsilyl azide

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About This Item

Linear Formula:
(CH3)3SiN3
CAS Number:
Molecular Weight:
115.21
NACRES:
NA.23
PubChem Substance ID:
eCl@ss:
39100709
UNSPSC Code:
12352103
EC Number:
225-078-5
MDL number:
Beilstein/REAXYS Number:
1903730
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Quality Level

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

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

Regulatory Information

危险化学品

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Articles

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.

Click chemistry, and the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) in particular, is a powerful new synthetic tool in polymer chemistry and material science.


Synthesis, 106-106 (1988)
Journal of the American Chemical Society, 116, 4501-4501 (1994)
Journal of the American Chemical Society, 115, 9347-9347 (1993)



Global Trade Item Number

SKUGTIN
155071-10G04061838741851
155071-50G04061838741868