Trimethylsilyl azide, 94%

Name: Trimethylsilyl azide, 94%
SKU: L00173.22

CAS: 4648-54-8 | C3H9N3Si | 115.21 g/mol

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数量:

5 g

25 g

100 g

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製品番号（カタログ番号） L00173.22

または、製品番号L00173-22

価格（JPY）

数量:

100 g

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化学物質識別子

CAS4648-54-8

仕様

スペックシート

FormLiquid

CommentSpecification differs for U.S. and non-U.S. material where indicated

Appearance (Color)Clear to slightly hazy colorless to pale pink

Refractive Index1.4110-1.4180 @ 20°C (non-U.S. specification)

Assay (GC)≥92.0%

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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

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.

Solubility
Miscible with toluene, dichloromethane, diethyl ether and most organic solvents.

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

RUO – Research Use Only

General References:

A mild, convenient synthesis of alkyl azides involves S_N2 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-butyl tin 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).