ALLYLTRIMETHOXYSILANE

Product Code: SIA0540.0
CAS No: 2551-83-9
SDS Sheets: EU | US
Navigate this page...
COMMERCIAL
2551-83-9
Save for Later
Pack Size
Quantity
Price
 
10 g
$200.00
50 g
$213.00
2 kg
$1,344.00
16 kg
Contact Us For Pricing
150 kg
Contact Us For Pricing

Prices listed are EXW price (Morrisville, PA US) in USD. Prices vary depending on currency and Incoterms.

Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    219-855-8
  • HMIS

    3-2-1-X
  • Molecular Formula

    C6H14O3Si
  • Molecular Weight (g/mol)

    162.26
  • Purity (%)

    97%
  • TSCA

    Yes
  • Boiling Point (˚C/mmHg)

    146-148
  • Density (g/mL)

    0.963
  • Density Temperature (˚C)

    25
  • Flash Point (˚C)

    46 °C
  • Refractive Index @ 20˚C

    1.4036

Additional Properties

  • Hydrolytic Sensitivity

    7: reacts slowly with moisture/water

    • Application

    Allylation of ketones, aldehydes and imines with dual activation of a Lewis Acid and fluoride ion.1
    Used in the regioselective generation of the thermodynamically more stable enol trimethoxysilyl ethers, which in turn are used in the asymmetric generation of quaternary carbon centers.2
    Converts arylselenyl bromides to arylallylselenides.3
    Allylates aryl iodides.4

    Fieser

    F&F: Vol 18, p 14; Vol 19, p 360; Vol 20, p 85; Vol 21, p 3, Vol 12, p 395

    Reference

    1. Yamasaki, S. et al. J. Am. Chem. Soc. 2002, 124, 6536.
    2. Ichibakase, T. et al. Tetrahedron Lett. 2008, 49, 4427.
    3. Bhadra, S. et al. J. Org. Chem. 2010, 75, 4864.
    4. Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 1684.

    Safety

  • Packaging Under

    Nitrogen

    • Olefin Functional Trialkoxy Silane

    Silane coupling agents have the ability to form a durable bond between organic and inorganic materials to generate desired heterogeneous environments or to incorporate the bulk properties of different phases into a uniform composite structure. The general formula has two classes of functionality. The hydrolyzable group forms stable condensation products with siliceous surfaces and other oxides such as those of aluminum, zirconium, tin, titanium, and nickel. The organofunctional group alters the wetting or adhesion characteristics of the substrate, utilizes the substrate to catalyze chemical transformations at the heterogeneous interface, orders the interfacial region, or modifies its partition characteristics, and significantly effects the covalent bond between organic and inorganic materials.

    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.

    Allyltrimethoxysilane; 1-Trimethoxysilylprop-2-ene

  • Adhesion promoter for vinyl-addition silicones
  • Allylation of ketones, aldehydes and imines with dual activation of a Lewis Acid and fluoride ion
  • Used in the regioselective generation of the thermodynamically more stable enol trimethoxysilyl ethers, which in turn are used in the asymmetric generation of quaternary carbon centers
  • Converts arylselenyl bromides to arylallylselenides
  • Allylates aryl iodides
  • Used in microparticle surface modification
  • Comonomer for polyolefin polymerization
  • 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

    • Silicon Chemistry, Articles

    Silicon-Based Formation of Carbon-Carbon Bonds – Larson

    Hatanaka and Hiyama first reported the palladium-catalyzed, fluoride-promoted reaction of aryl, alkenyl, allyl, and ethynyltrimethylsilanes with aryl, vinil and allyl halides to form the respective cross-coupled products