4648-54-8

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TRIMETHYLSILYL AZIDE, 96%

Product Code: SIT8580.0

Cas No: 4648-54-8

R&D quantities:

2 kg
$1,710.00
50 g
$187.00
10 g
$48.00
  • CAUTION: HIGHLY TOXIC
  • CAN FORM EXPLOSIVE PRODUCTS WITH MONOVALENT HEAVY METALS (Cu, Ag, Pb) AND VINYLSILANES
  • AVOID CONTACT WITH METALS
  • Boiling Point: 95-6°

    EINECS Number: 225-078-5

    Melting Point: -95°

    Molecular Weight: 115.21

    Alternative Name: AZIDOTRIMETHYLSILANE

    Specific Gravity: 0.876

    Flashpoint: 30°C (86°F)

    HMIS Key: 4-3-2-X

    Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents

    Formula: C3H9N3Si

    Purity: 96%

    Refractive Index: 1.4140

    TSCA: TSCA

    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

    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.

    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.

    Additional Properties: 300
    Soluble in hydrocarbons
    Replaces hydrazoic acid