TRIMETHYLSILYL AZIDE, 96%

Product Code: SIT8580.0
CAS No: 4648-54-8
SDS Sheets: EU | US
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10 g
$82.00
50 g
$318.00
2 kg
$2,256.00
15 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    225-078-5
  • Synonyms

    AZIDOTRIMETHYLSILANE
  • HMIS

    4-3-2-X
  • Molecular Formula

    C3H9N3Si
  • Molecular Weight (g/mol)

    115.21
  • Purity (%)

    96%
  • TSCA

    Yes
  • Autoignition Temp (˚C)

    300
  • Boiling Point (˚C/mmHg)

    95-96
  • Density (g/mL)

    0.876
  • Flash Point (˚C)

    30 °C
  • Melting Point (˚C)

    -95°
  • Refractive Index @ 20˚C

    1.4140

Additional Properties

  • Hydrolytic Sensitivity

    8: reacts rapidly with moisture, water, protic solvents
  • Application

    Review of synthetic utility.1
    Used in the preparation of glycosyl azides.2
    Reacts with terminal acetylenes and allyl carbonates to give 1-allyl-3-substituted 1,2,3-triazoles.3
    Used to prepare the energetically unstable 2,5,8-triazido-s-heptazine.4
    Converts alcohols directly to azides with complete inversion.5
    Used in a one-pot, click-conversion of amines to triazoles.6
    Converts allyl alcohols to allyl azides.7
    Reaction with bridged bicyclic olefins leads to 1,2,3-triazoles by retro-Diels-Alder reaction.8

    Fieser

    F&F: Vol. 1, p 1236; Vol. 3, p 316; Vol. 5, p 354, p 719; Vol. 6, p 561, p 632; Vol. 9, p 21; Vol. 10, p 14, p 113; Vol. 11, p 32; Vol. 12, p 37; Vol. 13, p 34; Vol. 14, p 25; Vol. 15, p 16, p 342; Vol. 16, p 17; Vol. 17, p 23,p 157,p 378; Vol. 18, p 379, p 380; Vol. 19, p 371; Vol. 20, p 201,p 403; Vol. 21, p 151.

    Reference

    1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 26-31.
    2. Soli, E. D.; DeShong, P. J. Org. Chem. 1999, 64, 9724.
    3. Kamijo, S. et al. J. Am. Chem. Soc. 2003, 125, 7786.
    4. Miller, D. R. et al. J. Am. Chem. Soc. 2004, 126, 5372.
    5. Mukaiyama, T. et al. Chem. Lett. 2008, 37, 1072.
    6. Savonnet, M. et al. J. Am. Chem. Soc. 2010, 132, 4418.
    7. Ruepling, M. et al. Org. Lett. 2012, 15, 768.
    8. Peterson, W. et al. J. Organomet. Chem. 1976, 121, 285.

    Safety

  • Packaging Under

    Nitrogen
  • CAUTION: HIGHLY TOXIC
  • CAN FORM EXPLOSIVE PRODUCTS WITH MONOVALENT HEAVY METALS (Cu, Ag, Pb) AND VINYLSILANES
  • AVOID CONTACT WITH METALS
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