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
InChI key
SEDZOYHHAIAQIW-UHFFFAOYSA-N
InChI
1S/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3
SMILES string
C[Si](C)(C)N=[N+]=[N-]
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
Quality Level
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.
signalword
Danger
hcodes
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
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Covalent functionalization of epitaxial graphene by azidotrimethylsilane
Choi, Junghun, et al.
The Journal of Physical Chemistry C, 113(22), 9433-9435 (2009)
Azidotrimethylsilane
Li, B. L.
Synlett, 23(10), 1554-1555 (2012)
Synthesis, 106-106 (1988)
Journal of the American Chemical Society, 116, 4501-4501 (1994)
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
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