Azidotrimethylsilane

Product Name: Azidotrimethylsilane
CAS No.: 4648-54-8
Chemical Name: Azidotrimethylsilane
Synonyms: TMSN3;TRIMETHYLSILYL AZIDE;TMSiA;(CH3)3SiN3;decomposes;Trimethylazidosilane;Three methyl azide silane;CFS-548;AzidotrimethyL;Co-Formula CFS-548
CBNumber: CB3444416
Molecular Formula: C3H9N3Si
Formula Weight: 115.21
MOL File: 4648-54-8.mol

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Azidotrimethylsilane Property

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
Specific Gravity: 0.868
color: Clear colorless to slightly yellow
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)
NIST Chemistry Reference: Azidotrimethylsilane(4648-54-8)
EPA Substance Registry System: Azidotrimethylsilane (4648-54-8)

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Safety

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
F: 10-33
Autoignition Temperature: 300 °C
TSCA: Yes
HazardClass: 3
PackingGroup: II
HS Code: 29310095

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 155071
Product name: Azidotrimethylsilane
Purity: 95%
Packaging: 10g
Price: $107
Updated: 2024/03/01

Sigma-Aldrich

Product number: 8.18026
Product name: Trimethylsilyl azide
Purity: for synthesis
Packaging: 25mL
Price: $147
Updated: 2024/03/01

Sigma-Aldrich

Product number: 155071
Product name: Azidotrimethylsilane
Purity: 95%
Packaging: 50g
Price: $310
Updated: 2024/03/01

TCI Chemical

Product number: T0801
Product name: Trimethylsilyl Azide
Purity: >95.0%(GC)
Packaging: 5g
Price: $26
Updated: 2024/03/01

TCI Chemical

Product number: T0801
Product name: Trimethylsilyl Azide
Purity: >95.0%(GC)
Packaging: 25g
Price: $76
Updated: 2024/03/01

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Azidotrimethylsilane Chemical Properties,Usage,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

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.

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).

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.]

Azidotrimethylsilane Preparation Products And Raw materials

Raw materials

Hexamethylphosphoramide Sodium azide Chlorotrimethylsilane Phosphite III

Preparation Products

2,2-DICHLORO-1-METHYLCYCLOPROPANAMINE

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View Lastest Price from Azidotrimethylsilane manufacturers

Hebei Weibang Biotechnology Co., Ltd

Product: Azidotrimethylsilane 4648-54-8
Price: US $10.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 10 mt
Release date: 2024-11-21

Hebei Chuanghai Biotechnology Co,.LTD

Product: Azidotrimethylsilane 4648-54-8
Price: US $10.00/KG
Min. Order: 1KG
Purity: 99.8%
Supply Ability: 100tons
Release date: 2024-08-16

Hebei Mojin Biotechnology Co., Ltd

Product: Azidotrimethylsilane 4648-54-8
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 50000KG/month
Release date: 2023-06-21

4648-54-8, AzidotrimethylsilaneRelated Search:

CHLORODIMETHYLVINYLSILANE Methyltrimethoxysilane Hexamethyldisilane (Trifluoromethyl)trimethylsilane tert-Butyldimethylsilyl chloride Silicon nitride Methyltrichlorosilane N-(Trimethylsilyl)acetamide Methyltriethoxysilane Dichlorodimethylsilane Methyltris(methylethylketoxime)silane TRIMETHYLSILANE Iodotrimethylsilane Trimethylsilyl cyanide N-(Trimethylsilyl)imidazole Sodium azide METHYLSILANE Hydrazoic acid

TRIMETHYLSILYL AZIDE

(CH3)3SiN3

azidotrimethyl-silan

Silane, azidotrimethyl-

Silane,azidotrimethyl-

Azidotrimethylsilane ,95%

Azidotrimethylsilane,Trimethylsilyl azide

TMSiA

TMSN3

TRIMETHYLSILYL AZIDE FOR SYNTHESIS

AzidotriMethylsilane, 97% 10ML

TriMethylsilyl azid

Trimethylsilyl azide (TMSA)

AzidotrimethyL

zidotrimethylsilane

1-(Trimethylsilyl)-1,3-diaza-2-azoniapropadiene-3-ide

Trimethylazidosilane

AZIDOTRIMETHYLSILANE

Trimethylsilylazide,95%

Trimethylsilylazide,typically95%

Azidotrimethyl silane(97%)

Trimethylsilylazide, typically 95%

Trimethylsilyl azide,98+%

Co-Formula CFS-548

CFS-548

TrimethylsilylAzide&gt

Trimethylsilyl azide, 93%, for synthesis

decomposes

Three methyl azide silane

Azidotrimethylsilane, 94%,

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.