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4648-54-8 - Trimethylsilyl azide, 94% - Azidotrimethylsilane - L00173 - Alfa Aesar

L00173 Trimethylsilyl azide, 94%

CAS Number
4648-54-8
Synonyms
Azidotrimethylsilane

Size Price ($) Quantity Availability
5g 29.56
25g 81.58
100g 247.20
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Trimethylsilyl azide, 94%

MDL
MFCD00001986
EINECS
225-078-5

Chemical Properties

Formula
C3H9N3Si
Formula Weight
115.21
Melting point
-95°
Boiling Point
95-99°
Flash Point
6°(42°F)
Density
0.872
Refractive Index
1.4140
Sensitivity
Moisture Sensitive
Solubility
Miscible with toluene, dichloromethane, diethyl ether and most organic solvents.

Applications

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.

Notes

Moisture sensitive. Store in a cool place. Incompatible with strong oxidizing agents and strong acids.

Literature References

A mild, convenient synthesis of alkyl azides involves SN2 reaction with the corresponding alkyl halide, phosphate or tosylate, promoted by TBAF: Synthesis, 376 (1995).

Non-explosive hydrazoic acid equivalent in many cycloaddition reactions: e.g. with alkynes to give 1,2,3-triazoles: Chem. Ber., 99, 2512 (1966), nitriles, catalyzed by Di-n-butyl­tin oxide, L14491 , to give tetrazoles: J. Org. Chem., 58, 4139 (1993).

Curtius reaction with acid halides gives isocyanates in one operation: Synth. Commun., 2, 227 (1972): Synthesis, 551 (1972); J. Org. Chem., 38, 2982 (1973). Similarly, pyridine-2,3-dicarboxylic anhydride is converted to 3-azaisatoic anhydride: Synthesis, 972 (1982):

In combination withSnCl4,ß-D-ribofuranosyl acetates are converted to azides: Carbohydr. Res., 232, 359 (1992). Similarly, reaction with tert-halides in the presence of tin(IV) chloride gives tert-azides, which can be converted to iminophosphoranes by Staudinger reduction with Triethyl­ phosphite, L00339 . Hydrolysis completes a one-pot sequence for the conversion of a tert-halide to the corresponding amine: Synthesis, 487 (1987).

In combination with triflic acid, is useful for the direct amination of aromatics. Aminodiazonium triflate is suggested as the active intermediate. Thus, benzene gives aniline in 95% yield and toluene gives a mixture of o- and p-toluidine: J. Org. Chem., 54, 1203 (1989). See also: Tetrahedron Lett., 32, 4321 (1991).

Mitsunobu reaction, in the presence of DIAD, with 1,2- and 1,3-diols leads to regioselective, stereospecific azidation to give predominantly the 2- or 3-azido alcohol with inversion of configuration: J. Org. Chem., 64, 6049 (1999).

For reviews, see: Chem. Soc. Rev., 7, 15 (1978); Synthesis, 861 (1980); Chem. Rev., 88, 351 (1988).

Cui, T.; Smith, R.; Zhu, X. Stereoselective synthesis of alpha-glycosyl azides by ring-opening of 1, 6-anhydrosugars with trimethylsilyl azide. Carbohydr. Res. 2015, 416, 14-20.

Tandiary, M. A.; Masui, Y.; Onaka, M. A combination of trimethylsilyl chloride and hydrous natural montmorillonite clay: an efficient solid acid catalyst for the azidation of benzylic and allylic alcohols with trimethylsilyl azide. RSC Adv. 2015, 5 (20), 15736-15739.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H301-H311-H330-H400-H410

Highly flammable liquid and vapour. Toxic if swallowed. Toxic in contact with skin. Fatal if inhaled. Very toxic to aquatic life. Very toxic to aquatic life with long lasting effects.

Precautionary Statements: P210-P260-P301+P310-P303+P361+P353-P304+P340-P320-P330-P361-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Specific treatment is urgent (see label). Rinse mouth. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1903730
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2931.90
TSCA
Yes

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