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762-72-1

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ALLYLTRIMETHYLSILANE

Product Code: SIA0555.0

Cas No: 762-72-1

R&D quantities:

1.5 kg
$901.50
100 g
$174.00
25 g
$54.00
Trimethylsilyl Blocking Agent

Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.

Alkenylsilane Cross-Coupling Agent

The cross-coupling reaction is a highly useful methodology for the formation of carbon-carbon bonds. It involves two reagents, with one typically being a suitable organometallic reagent - the nucleophile - and the other a suitable organic substrate, normally an unsaturated halide, tosylate or similar - the electrophile.

Allytrimethylsilane; Propenyltrimethylsilane; 3-Trimethylsilylpropene
  • Neutral propylene by-product
  • Acid-catalyzed silylations
  • Used for acids and thiols
  • Employed in the synthesis of N-trimethylsilylpyridinium triflate an active trimethylsilylating agent
  • Nafion SAC-13 has been shown to be a recyclable catalyst for the trimethylsilylation of primary, secondary, and tertiary alcohols in excellent yields and short reaction times
  • Reacts with vinyl bromides to give 1,4-dienes and
  • Versatile synthon- transfers allyl group, highly nucleophilic double bond
  • Undergoes polymerization with zirconocene complexes
  • Provides functional termination of living carbocationic polymerized polyisobutylenes
  • Allylates dioxolanes
  • Provides alternative for the formation of trans-allyl-2,3-O-isopropylidene-protected pyrrolidines
  • Carries out deoxygenative allylation of benzylic alcohols
  • Allylates imines under fluoride catalysis
  • Reacts with allyl bromides to give 1,5-dienes
  • Diallylates ketones via their ketals
  • Forms benzylic homoallylic alcohols in a 3-component reaction with aldehydes
  • Allylates lithium alkoxides w/ loss of the lithium oxide
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure
  • Extensive review of silicon based cross-coupling agents: Denmark, S. E. et al. "Organic Reactions, Volume 75" Denmark, S. E. ed., John Wiley and Sons, 233, 2011
  • Boiling Point: 85-6°

    EINECS Number: 212-104-5

    Molecular Weight: 114.26

    Specific Gravity: 0.7193

    Flashpoint: 7°C (45°F)

    HMIS Key: 2-4-0-X

    Hydrolytic Sensitivity: 2: reacts with aqueous acid

    Formula: C6H14Si

    Refractive Index: 1.4074

    TSCA: TSCA

    Application: Key reviews.1,2,3,4
    Carries out deoxygenative allylation of benzylic alcohols.10
    Allylates lithium alkoxides w/ loss of the lithium oxide.11
    Forms benzylic homoallylic alcohols in a 3-component reaction w/ aldehydes.12
    Diallylates ketones via their ketals.13
    Undergoes polymerization with zirconocene complexes.5
    Provides functional termination of living carbocationic polymerized polyisobutylenes.6
    Allylates dioxolanes.7
    Allylates imines under fluoride catalysis.8
    Provides alternative for the formation of trans-allyl-2,3-O-isopropylidene-protected pyrrolidines.9

    Reference: 1. Handbook for Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 14-24.
    10. De, S. K.; Gibbs, R. A. Tetrahedron Lett. 2005, 46, 8345.
    11. Kabalka, G. W. et al. Organometallics 2007, 26, 4112.
    12. Kataki, D.; Phukan, P. Tetrahedron Lett. 2009, 50, 1958.
    13. Galy, N. et al. Tetrahedron 2011, 67, 1448.
    2. Weber, W. In Silicon Reagents for Organic Synthesis; Springer-Verlag: 1983, p173.
    3. Fleming, I. Synthesis 1979, 761.
    4. Hosomani, N. Acc. Chem. Res. 1988, 21, 200.
    5. Habane, S. et al. Macromol. Chem. Phys. 1998, 199, 2211.
    6. Wilczek, L. et al. J. Polym. Sci., Part A: Polym. Chem. 1987, 25, 3255.
    7. Dussault, P. H.;Liu, X. Org. Lett. 1999, 1, 1391.
    8. Weng, D. K. et al. J. Org. Chem. 1999, 64, 4233.
    9. De Armas, P. et al. Org. Lett. 2000, 3, 3513.

    Fieser:

    Additional Properties: Versatile synthon - transfers allyl group, highly nucleophilic double bond