VINYLTRIMETHOXYSILANE

Product Code: SIV9220.0
CAS No: 2768-02-7
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25 g
$15.00
2 kg
$114.00
16 kg
$548.00
180 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    220-449-8
  • HMIS

    3-3-1-X
  • Molecular Formula

    C5H12O3Si
  • Molecular Weight (g/mol)

    148.23
  • TSCA

    Yes
  • Autoignition Temp (˚C)

    235
  • Boiling Point (˚C/mmHg)

    123
  • Density (g/mL)

    0.970
  • Flash Point (˚C)

    28
  • Refractive Index @ 20˚C

    1.3930
  • Specific Wetting (m2/g)

    528
  • Viscosity at 25 ˚C (cSt)

    0.6

Additional Properties

  • Hydrolytic Sensitivity

    7: reacts slowly with moisture/water

    • Application

    Employed in two-stage1 and one-stage2 graft polymerization/crosslinking for PE
    Copolymerizes with ethylene to form moisture crosslinkable polymers.3
    Converts arylselenyl bromides to arylvinylselenides.4
    Reacts with anhydrides to transfer both vinyl and methoxy and thus form the mixed diester.5
    Cross-couples w/ ?-bromo esters to give ?-vinyl esters in high ee.6

    Reference

    1. Scott, H. U.S. Patent 3,646,155, 1972.
    2. Swarbrick, P. et al. U.S. Patent 4,117,195, 1978.
    3. Isaka, T. et al. U.S. Patent 4,413,066, 1983.
    4. Bhadra, S. et al. J. Org. Chem. 2010, 75, 4864.
    5. Luo, F. et al. J. Org. Chem. 2010, 75, 5379.
    6. Strotman, N. A.; Sommer, S.; Fu, G. C. Angew. Chem., Int. Ed. Engl. 2007, 46, 3556.

    Safety

  • Hazard Info

    oral rat, LD50: 8,000 mg/kg
  • 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.

    Vinyltrimethoxysilane; Ethenyltrimethoxysilane; Trimethoxyvinylsilane; Trimethoxysilylethylene, VTMS

  • Viscosity: 0.6 cSt
  • Copolymerization parameters- e,Q: -0.38, 0.031
  • Specific wetting surface area: 528 m2/g
  • Vapor pressure, 20 °C: 9 mm
  • Employed in two-stage and one-stage graft polymerization/crosslinking for polyethylene (PE)
  • Copolymerizes with ethylene to form moisture crosslinkable polymers
  • Converts arylselenyl bromides to arylvinylselenides
  • Reacts with anhydrides to transfer both vinyl and methoxy and thus form the mixed diester
  • Cross-couples with α-bromo esters to give α-vinyl esters in high ee
  • Used in microparticle surface modification
  • For vinylations
  • Alkenyltrialkoxysilanes react w/ aryl bromides and iodides to form styrenes under fluoride- and ligand-free and aqeous conditions
  • Reacts in presence of fluoride
  • 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