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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%

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

Application

Versatile azidonation reagent for amines, amides, aldehydes, and ketones.

Packaging

10, 50 g in glass bottle

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 Code

3 - Flammable liquids

WGK Germany

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

Certificate of Analysis

Certificate of Origin

Synthesis, 106-106 (1988)
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)
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...
Journal of the American Chemical Society, 115, 9347-9347 (1993)
Covalent functionalization of epitaxial graphene by azidotrimethylsilane
Choi, Junghun, et al.
The Journal of Physical Chemistry C, 113(22), 9433-9435 (2009)

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.

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Hydroazidation Catalyst

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

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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