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155071

Sigma-Aldrich

Azidotrimethylsilane

95%

Synonyme(s) :

Trimethylsilyl azide

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About This Item

Formule linéaire :
(CH3)3SiN3
Numéro CAS:
4648-54-8
Poids moléculaire :
115.21
Beilstein:
1903730
Numéro CE :
225-078-5
Numéro MDL:
MFCD00001986
Code UNSPSC :
12352103
eCl@ss :
39100709
ID de substance PubChem :
24849336
Nomenclature NACRES :
NA.23
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Essai

95%

Forme

liquid

Indice de réfraction

n20/D 1.414 (lit.)

pb

52-53 °C/175 mmHg (lit.)

Densité

0.868 g/mL at 25 °C (lit.)

Température de stockage

2-8°C

Chaîne SMILES 

C[Si](C)(C)N=[N+]=[N-]

InChI

1S/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3

Clé InChI

SEDZOYHHAIAQIW-UHFFFAOYSA-N

Description générale

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.[1]

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.

Pictogrammes

FlameSkull and crossbones
GHS02,GHS06

Mention d'avertissement

Danger

Mentions de danger

H225,H301 + H311 + H331

Classification des risques

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

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

42.8 °F - closed cup

Point d'éclair (°C)

6 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificats d'analyse (COA)

Lot/Batch Number
SDBB1912
STBH9843
STBG3028V
STBF0857V
STBD0393V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Synthesis, 106-106 (1988)
Azidotrimethylsilane
Li, B. L.
Synlett, 23(10), 1554-1555 (2012)
Covalent functionalization of epitaxial graphene by azidotrimethylsilane
Choi, Junghun, et al.
The Journal of Physical Chemistry C, 113(22), 9433-9435 (2009)
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)
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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.

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.

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.

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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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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