TRIMETHYLSILYL AZIDE, 96%

Product Code: SIT8580.0
CAS No: 4648-54-8
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50 g
$366.00
2 kg
$2,595.00
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

    • Archived, Publications & Technical Reports

    Chemistry of Azidosilanes — Peterson

    Applied Technology

    Emerging Molecular and Atomic Level Techniques for Nanoscale Applications

    This overview provides an introduction and comparison of emerging processing technologies that represent the best contenders to satisfy future demands for ultrathin film applications.