| Identification | More | [Name]
Azidotrimethylsilane | [CAS]
4648-54-8 | [Synonyms]
AZIDOTRIMETHYLSILANE
TRIMETHYLSILYL AZIDE
(CH3)3SiN3
azidotrimethyl-silan
Silane, azidotrimethyl-
Silane,azidotrimethyl-
Trimethylsilylazide,95%
Trimethylsilylazide,typically95%
zidotrimethylsilane
Azidotrimethyl silane(97%)
Trimethylsilylazide, typically 95%
1-(Trimethylsilyl)-1,3-diaza-2-azoniapropadiene-3-ide
Trimethylazidosilane | [EINECS(EC#)]
225-078-5 | [Molecular Formula]
C3H9N3Si | [MDL Number]
MFCD00001986 | [Molecular Weight]
115.21 | [MOL File]
4648-54-8.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to slightly yellow liquid | [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. ]
Refrigerator | [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 | [Hydrolytic Sensitivity]
8: reacts rapidly with moisture, water, protic solvents | [Sensitive ]
Moisture Sensitive | [BRN ]
1903730 | [InChI]
1S/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3 | [InChIKey]
SEDZOYHHAIAQIW-UHFFFAOYSA-N | [SMILES]
C[Si](C)(C)N=[N+]=[N-] | [CAS DataBase Reference]
4648-54-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Azidotrimethylsilane(4648-54-8) | [EPA Substance Registry System]
4648-54-8(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
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 ]
R11:Highly Flammable.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R29:Contact with water liberates toxic gas. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S8:Keep container dry .
S57:Use appropriate container to avoid environmental contamination .
S36/37:Wear suitable protective clothing and gloves .
S29:Do not empty into drains . | [RIDADR ]
UN 1992 3/PG 2
| [WGK Germany ]
3
| [F ]
10-33 | [Autoignition Temperature]
300 °C | [TSCA ]
Yes | [REACH Registrations]
Active | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29310095 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Acute Tox. 3 Dermal
Acute Tox. 3 Inhalation
Acute Tox. 3 Oral
Flam. Liq. 2 |
| Hazard Information | Back Directory | [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]
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.] | [References]
[1] XIAO‐PING YIN Jian Z Lei Zhu. Metal‐Free Azidation of α‐Hydroxy Esters and α‐Hydroxy Ketones Using Azidotrimethylsilane[J]. Advanced Synthesis & Catalysis, 2018, 360 6: Pages 1116-1122. DOI:10.1002/adsc.201701345.
[2] RUI ZHANG . Iron‐Mediated Azidomethylation or Azidotrideuteromethylation of Active Alkenes with Azidotrimethylsilane and Dimethyl Sulfoxide[J]. Advanced Synthesis & Catalysis, 2018, 360 7: Pages 1384-1388. DOI:10.1002/adsc.201800078.
[3] ZHU Y, CHU Q, LI H, et al. Electrochemical primary amination of imidazopyridines with azidotrimethylsilane under mild conditions†[J]. Green Chemistry, 2022, 1: 296-300. DOI:10.1039/D2GC03703C.
[4] JUNGHUN CHOI. Covalent Functionalization of Epitaxial Graphene by Azidotrimethylsilane[J]. The Journal of Physical Chemistry C, 2009, 29 24 1: 9433-9435. DOI:10.1021/JP9010444.
[5] Li, Bao-Le. "Azidotrimethylsilane." Synlett 23.10 (2012): 1554-1555.
[6] Groutas, William C., and David Felker. "Synthetic applications of cyanotrimethylsilane, lodotrimethylsilane, azidotrimethylsilane, and methylthiotrimethylsilane." Synthesis 1980.11 (1980): 861-868. |
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