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155071

Sigma-Aldrich

Azidotrimethylsilane

95%

Synonym(s):
Trimethylsilyl azide
Linear Formula:
(CH3)3SiN3
CAS Number:
Molecular Weight:
115.21
Beilstein:
1903730
EC Number:
MDL number:
eCl@ss:
39100709
PubChem Substance ID:
NACRES:
NA.23

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

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This Item
95541923608.18026
Azidotrimethylsilane 95%

Sigma-Aldrich

155071

Azidotrimethylsilane

Chlorotrimethylsilane produced by Wacker Chemie AG, Burghausen, Germany, ≥99.0% (GC)

Sigma-Aldrich

95541

Chlorotrimethylsilane

Chlorotrimethylsilane puriss., ≥99.0% (GC)

Sigma-Aldrich

92360

Chlorotrimethylsilane

Trimethylsilyl azide for synthesis

Sigma-Aldrich

8.18026

Trimethylsilyl azide

bp

52-53 °C/175 mmHg (lit.)

bp

57 °C (lit.)

bp

57 °C (lit.)

bp

-

density

0.868 g/mL at 25 °C (lit.)

density

0.856 g/mL at 25 °C (lit.)

density

0.856 g/mL at 25 °C (lit.)

density

0.87-0.88 g/cm3 at 20 °C

assay

95%

assay

≥99.0% (GC)

assay

≥99.0% (GC)

assay

≥90.0% (GC)

form

liquid

form

liquid

form

liquid

form

liquid

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

15-25°C

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

42.8 °F - closed cup

Flash Point(C)

6 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Customers Also Viewed

Covalent functionalization of epitaxial graphene by azidotrimethylsilane
Choi, Junghun, et al.
The Journal of Physical Chemistry C, 113(22), 9433-9435 (2009)
Journal of the American Chemical Society, 116, 4501-4501 (1994)
Journal of the American Chemical Society, 115, 9347-9347 (1993)
James T Goettel et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 26(5), 1136-1143 (2019-11-30)
A cyclic (alkyl)(amino)carbene (CAAC) has been shown to react with a covalent azide similar to the Staudinger reaction. The reaction of Me CAAC with trimethylsilyl azide afforded the N-silylated 2-iminopyrrolidine (Me CAAC=NSiMe3 ), which was fully characterized. This compound undergoes
Synthesis, 106-106 (1988)

Articles

Introduction of Terminal Azide and Alkyne Functionalities in Polymers

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.

Organic Azides and Azide Sources

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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