Trimethylsilyl azide

• Catalog No.: L00173
• CAS Number: 4648-54-8
• M. F.: C3H9N3Si
• M. W.: 115.20916
• Purity: 94%

SYNONYMS

• Title: 叠氮化三甲基硅烷
• IUPAC name: azidotrimethylsilane
• IUPAC Traditional name: trimethylsilyl azide
• Synonyms: Azidotrimethylsilane

DATABASE IDS

• MDL Number: MFCD00001986
• EC Number: 225-078-5
• CAS Number: 4648-54-8
• Beilstein Number: 1903730

PROPERTIES

• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN1992
• Packing Group: II
• GHS Hazard statements: H225-H300-H310-H330-H400-H410
• European Hazard Symbols: Toxic (T)
• European Hazard Symbols: Flammable (F)
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P304+P340-P320-P330-P361-P405-P501A
• Risk Statements: 11-23/24/25-29-50/53
• Safety Statements: 7/8-9-16-23-27-30-33-36/37/39-45-57-60
• Purity: 94%
• Boiling Point: 95-99°C
• Density: 0.872
• Flash Point: 6°C(42°F)
• Melting Point: -95°C
• Refractive Index: 1.4140

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-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,?-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).