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155071

Sigma-Aldrich

Azidotrimethylsilane

95%

Synonym(s):

Trimethylsilyl azide

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About This Item

Linear Formula:
(CH3)3SiN3
CAS Number:
4648-54-8
Molecular Weight:
115.21
Beilstein:
1903730
EC Number:
225-078-5
MDL number:
MFCD00001986
UNSPSC Code:
12352103
eCl@ss:
39100709
PubChem Substance ID:
24849336
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
GHS02,GHS06

Signal Word

Danger

Hazard Statements

H225,H301 + H311 + H331

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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