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Azidotrimethylsilane

CAS No.
4648-54-8
Chemical Name:
Azidotrimethylsilane
Synonyms
TMSN3;TRIMETHYLSILYL AZIDE;TMSiA;decomposes;(CH3)3SiN3;Trimethylazidosilane;Three methyl azide silane;CFS-548;AzidotrimethyL;Co-Formula CFS-548
CBNumber:
CB3444416
Molecular Formula:
C3H9N3Si
Molecular Weight:
115.21
MDL Number:
MFCD00001986
MOL File:
4648-54-8.mol
MSDS File:
SDS
Last updated:2023-06-21 21:49:59

Azidotrimethylsilane Properties

Melting point -95°C
Boiling point 92-95 °C(lit.)
Density 0.876 g/mL at 20 °C(lit.)
refractive index n20/D 1.415(lit.)
Flash point 74 °F
storage temp. 2-8°C
solubility Miscible with toluene, dichloromethane, diethyl ether and most organic solvents.
form Liquid
color Clear colorless to slightly yellow
Specific Gravity 0.868
Water Solubility decomposes
Sensitive Moisture Sensitive
Hydrolytic Sensitivity 8: reacts rapidly with moisture, water, protic solvents
BRN 1903730
InChIKey SEDZOYHHAIAQIW-UHFFFAOYSA-N
CAS DataBase Reference 4648-54-8(CAS DataBase Reference)
FDA UNII EM57JSM2Y9
NIST Chemistry Reference Azidotrimethylsilane(4648-54-8)
EPA Substance Registry System Azidotrimethylsilane (4648-54-8)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS02,GHS06
Signal word  Danger
Hazard statements  H225-H301+H311+H331
Precautionary statements  P210-P280-P301+P310+P330-P302+P352+P312-P304+P340+P311
Hazard Codes  F,T,N
Risk Statements  11-23/24/25-50/53-29
Safety Statements  16-36/37/39-45-8-57-36/37-29
RIDADR  UN 1992 3/PG 2
WGK Germany  3
10-33
Autoignition Temperature 300 °C
TSCA  Yes
HazardClass  3
PackingGroup  II
HS Code  29310095
NFPA 704
3
3 1
W

Azidotrimethylsilane price More Price(24)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 155071 Azidotrimethylsilane 95% 4648-54-8 10g $107 2024-03-01 Buy
Sigma-Aldrich 8.18026 Trimethylsilyl azide for synthesis 4648-54-8 25mL $147 2024-03-01 Buy
Sigma-Aldrich 155071 Azidotrimethylsilane 95% 4648-54-8 50g $310 2024-03-01 Buy
TCI Chemical T0801 Trimethylsilyl Azide >95.0%(GC) 4648-54-8 5g $26 2024-03-01 Buy
TCI Chemical T0801 Trimethylsilyl Azide >95.0%(GC) 4648-54-8 25g $76 2024-03-01 Buy
Product number Packaging Price Buy
155071 10g $107 Buy
8.18026 25mL $147 Buy
155071 50g $310 Buy
T0801 5g $26 Buy
T0801 25g $76 Buy

Azidotrimethylsilane Chemical Properties,Uses,Production

Chemical Properties

clear colorless to slightly yellow liquid

Physical properties

bp 95–96°C; n20 D 1.416; d 0.868 g cm?3; fp23°C; IR νmax 2100 cm?1; 1H NMR (CDCl3) δ = 0.22.

Uses

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

Uses

Many applications of TMSA in organic synthesis have been reported but only representative examples are described herein. Substitution Reactions. Benzyl,allyl,and substituted alkyl halides are converted to the corresponding azides in 60–100% yields via reactions with TMSA under neutral conditions in a nonaqueous solvent (eq 1).By using tin(IV) chloride as a catalyst, secondary and tertiary cyclic and polycyclic halides are similarly transformed into the corresponding azides in 50–92% yields (eq 1). Substitution Reactions of Azidotrimethylsilane

Uses

Trimethylsilyl azide is used as an azidonation reagent for amines, amides, aldehydes and ketones. It is involved in the preparation of alfa- and beta-siloxy azides from carbonyl compounds and epoxides. It is also used in the preparation of heterocyclic compounds and also acts as an effective substitute for hydrazoic acid. Further, it is used in the Oseltamivir total synthesis.

Preparation

several methods for the synthesis of this azide have been reported.The procedure involving aluminum chloride is not recommended, since an explosive product is formed.Azidotrimethylsilane is now commercially available, and a representative synthetic procedure is as follows. A mixture of sodium azide and chlorotrimethylsilane is refluxed in di-n-butyl ether for 2 days and the azide is safely distilled directly from the reaction vessel. Purer compound (99% content) is obtained by redistillation of the product. Several improved conditions have been reported for the preparation of this azide.In these procedures, trimethylsilyl chloride is reacted with sodium azide either neat or in a high boiling point solvent, such as a mixture of silicone oil and polyethylene glycol. Distillation of the crude product usually provides trimethylsilyl azide (TMSA) in high purity (97.9%) and yield (97%).

Purification Methods

Distil the azide through a Vigreux column (p 11) in a N2 atmosphere maintaining the oil bath temperature thermostat at 135-140o . Check the purity by 1H NMR [CHCl3, : single peak at 13cps from Me4Si]. Likely impurities are siloxane hydrolysis products. The azide is thermally stable even at 200o when it decomposes slowly without explosive violence. All the same, it is advisable to carry out the distillation behind a thick safety screen in a fumehood because unforseen EXPLOSIVE azides may be formed on long standing. [Birkofer & Wagner Org Synth Coll Vol VI 1030 1988.]

Global( 354)Suppliers
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View Lastest Price from Azidotrimethylsilane manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Azidotrimethylsilane pictures 2023-06-22 Azidotrimethylsilane
4648-54-8
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
Azidotrimethylsilane pictures 2023-03-06 Azidotrimethylsilane
4648-54-8
US $10.00 / KG 1KG 99.8% 100tons Hebei Guanlang Biotechnology Co,.LTD
Azidotrimethylsilane pictures 2023-02-14 Azidotrimethylsilane
4648-54-8
US $20.00 / kg 1kg 99% 5000 Ton Hebei Duling International Trade Co. LTD
azidotrimethyl-silan Silane, azidotrimethyl- Silane,azidotrimethyl- Azidotrimethylsilane ,95% Azidotrimethylsilane,Trimethylsilyl azide TRIMETHYLSILYL AZIDE FOR SYNTHESIS AzidotriMethylsilane, 97% 10ML TriMethylsilyl azid zidotrimethylsilane 1-(Trimethylsilyl)-1,3-diaza-2-azoniapropadiene-3-ide AZIDOTRIMETHYLSILANE Trimethylsilylazide,95% Trimethylsilylazide,typically95% Azidotrimethyl silane(97%) Trimethylsilylazide, typically 95% Trimethylsilyl azide (TMSA) AzidotrimethyL Trimethylsilyl azide,98+% Co-Formula CFS-548 CFS-548 TrimethylsilylAzide> Trimethylsilyl azide, 93%, for synthesis Azidotrimethylsilane, 94%, TRIMETHYLSILYL AZIDE TMSiA TMSN3 decomposes (CH3)3SiN3 Trimethylazidosilane Three methyl azide silane Azide trimethylsilane 4648-54-8 648-54-8 C3H10N2Si C3H9N3Si Azidation/Diazo Transfer Si (Classes of Silicon Compounds) Silicon Compounds (for Synthesis) Si-N Compounds Trimethylsilylazide, etc. Synthetic Reagents C-X Bond Formation (Non-Halogen) Si (Classes of Silicon Compounds) Silicon Compounds (for Synthesis) Si-N Compounds Synthetic Organic Chemistry Trimethylsilylazide, etc.