azidotrimethylsilane

• ChemBase ID: 88858
• Molecular Formular: C3H9N3Si
• Molecular Mass: 115.20916
• Monoisotopic Mass: 115.05657384
• SMILES: [Si](N=[N+]=[N-])(C)(C)C
• Canonical SMILES: C[Si](N=[N+]=[N-])(C)C
• InChI: InChI=1S/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3
• InChIKey: SEDZOYHHAIAQIW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: azidotrimethylsilane
• IUPAC Traditional name: trimethylsilyl azide
• Synonyms: Azidotrimethylsilane; Trimethylsilyl azide; Trimethylsilyl azide; Azidotrimethylsilane; Trimethylsilyl azide; azidotrimethylsilane; 三甲基硅叠氮; 叠氮三甲基硅烷; 叠氮三甲基硅烷; 三甲基叠氮化硅; 叠氮化三甲基硅烷

Database IDs

• CAS Number: 4648-54-8
• EC Number: 225-078-5
• MDL Number: MFCD00001986
• Beilstein Number: 1903730
• PubChem SID: 24849336; 162075756; 24889713
• PubChem CID: 78378
• Chemspider ID: 70747
• Wikipedia Title: Trimethylsilyl_azide

CALCULATED PROPERTIES

• Acid pKa: 5.0596914
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.0404
• LogD (pH = 7.4): 2.0404
• Log P: 2.1005
• Molar Refractivity: 28.2116 cm^3
• Polarizability: 11.4796295 Å^3
• Polar Surface Area: 29.43 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: reacts to form dangerous hydrazoic acid in water
• Apperance: clear liquid, color less
• Melting Point: -95°C
• Boiling Point: 52-53 °C/175 mmHg(lit.); 52-53°C at 175mmHg; 92-95°C at 760mmHg; 92-95 °C(lit.); 95-96°C/175mm; 95-99°C
• Flash Point: 42.8 °F; 6 °C; 6°C; 6°C(42°F)
• Auto Ignition Point: > 300 °C
• Density: 0.868 g/mL at 25 °C(lit.); 0.872; 0.876 g/mL at 20 °C(lit.); 0.8763 g/cm3 (20 C); 0.88
• Refractive Index: 1.4140; n20/D 1.414(lit.); n20/D 1.415(lit.)

Safety Information

• Storage Warning: Highly Flammable/Toxic/Moisture Sensitive/Keep Cold/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Flammable (F); Nature polluting (N); Toxic (T)
• UN Number: 1992; UN1992
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-23/24/25; 11-23/24/25-29-50/53; R11, R23, R24, R25, R29, R50, R51, R52, R53
• Safety Statements: 16-36/37/39-45; 7/8-9-16-23-27-30-33-36/37/39-45-57-60; S16,S29,S36, S37,S45,S57,S8,
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06; GHS09
• GHS Signal Word: Danger
• NFPA704:
  

  3

  4

  0
• GHS Hazard statements: H225-H300-H310-H330-H400-H410; H225-H301 + H311 + H331
• GHS Precautionary statements: P210-P261-P280-P301 + P310-P311; P210-P301+P310-P303+P361+P353-P304+P340-P320-P330-P361-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1992 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (GC); 94%; 95%
• Grade: purum
• Linear Formula: (CH3)3SiN3
• Empirical Formula (Hill Notation): C3H9N3Si

DETAILS

Sigma Aldrich - 155071

Packaging
10, 50 g in glass bottle
Application
Versatile azidonation reagent for amines,1 amides,2 aldehydes,3 and ketones.3

Sigma Aldrich - 92753

Other Notes
Stable, reactive source of azide, reviews1,2,3

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).