Azidotrimethylsilane

Azidotrimethylsilane Basic information
Product Name:Azidotrimethylsilane
Synonyms:azidotrimethyl-silan;Silane, azidotrimethyl-;Silane,azidotrimethyl-;Azidotrimethylsilane ,95%;Azidotrimethylsilane,Trimethylsilyl azide;TRIMETHYLSILYL AZIDE FOR SYNTHESIS;AzidotriMethylsilane, 97% 10ML;TriMethylsilyl azid
CAS:4648-54-8
MF:C3H9N3Si
MW:115.21
EINECS:225-078-5
Product Categories:Si (Classes of Silicon Compounds);Silicon Compounds (for Synthesis);Si-N Compounds;Synthetic Organic Chemistry;Trimethylsilylazide, etc.
Mol File:4648-54-8.mol
Azidotrimethylsilane Structure
Azidotrimethylsilane Chemical 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.)
Fp 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 Gravity0.868
Water Solubility decomposes
Sensitive Moisture Sensitive
Hydrolytic Sensitivity8: reacts rapidly with moisture, water, protic solvents
BRN 1903730
InChIKeySEDZOYHHAIAQIW-UHFFFAOYSA-N
CAS DataBase Reference4648-54-8(CAS DataBase Reference)
NIST Chemistry ReferenceAzidotrimethylsilane(4648-54-8)
EPA Substance Registry SystemAzidotrimethylsilane (4648-54-8)
Safety Information
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 Temperature300 °C
TSCA Yes
HazardClass 3
PackingGroup II
HS Code 29310095
MSDS Information
ProviderLanguage
Trimethylsilyl azide English
SigmaAldrich English
ACROS English
ALFA English
Azidotrimethylsilane Usage And Synthesis
Chemical Propertiesclear colorless to slightly yellow liquid
Physical propertiesbp 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.
UsesVersatile 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
UsesTrimethylsilyl 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.
Preparationseveral 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 MethodsDistil 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.]
Trimethylsilyl cyanide DIPHENYLMETHYLAZIDOSILANE Methyltris(methylethylketoxime)silane TRIMETHYLSILANE (Trifluoromethyl)trimethylsilane Sodium azide TRIPHENYLSILYLAZIDE Azidotrimethylsilane tert-Butyldimethylsilyl chloride Methyltriethoxysilane Azide TRIETHYLAZIDOSILANE METHYLSILANE Hydrazoic acid silicon nitride ceramics CHLORODIMETHYLVINYLSILANE N-(Trimethylsilyl)acetamide Methyltrimethoxysilane

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