VINYLTRIETHOXYSILANE

Product Code: SIV9112.0
CAS No: 78-08-0
SDS Sheets: EU | US
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78-08-0
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2 kg
$230.00
16 kg
$1,109.00
180 kg
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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

    201-081-7
  • HMIS

    1-2-1-X
  • Molecular Formula

    C8H18O3Si
  • Molecular Weight (g/mol)

    190.31
  • Purity (%)

    97%
  • TSCA

    Yes
  • Delta H Vaporization (kJ/mol)

    6.8 kcal/mole
  • Autoignition Temp (˚C)

    268
  • Boiling Point (˚C/mmHg)

    160-161
  • Density (g/mL)

    0.903
  • Flash Point (˚C)

    44 °C
  • Refractive Index @ 20˚C

    1.3960
  • Specific Wetting (m2/g)

    412

Additional Properties

  • Hydrolytic Sensitivity

    7: reacts slowly with moisture/water

    • Application

    Reacts with enamines to give (E)-?-silylenamines, which cross-couple w/ aryl iodides to give ?-aryl enamines.1
    Extensive review on the use in silicon-based cross-coupling reactions.2

    Reference

    1. Marciniec, B. et al. J. Org. Chem. 2005, 70, 8550.
    2. Denmark, S. E. et al. Organic Reactions, Vol. 75, Denmark, S. E. ed., John Wiley and Sons, 233, 2011.

    Safety

  • Hazard Info

    oral rat, LD50: 22,500 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.

    Vinyltriethoxysilane; Triethoxyvinylsilane; TEVS; VTES; Ethenyltriethoxysilane; Triethoxysilylethylene; Triethoxy(vinyl)silane

  • ΔHvap: 6.8 kcal/mol
  • ΔHform: -463.5 kcal/mol
  • Dipole moment: 1.69 debye
  • Specific wetting surface area: 412 m2/g
  • Copolymerization parameters- e,Q: -0.42, 0.028
  • γc of treated surfaces: 25 mN/m
  • Vapor pressure, 20 °C: 5 mm
  • Specific heat: 0.25 cal/g/°
  • Relative hydrolysis rate versus SIV9220.0, vinyltrimethoxysilane; 0.05
  • Forms copolymers with ethylene for moisture induced coupling of polyethylene
  • Couples fillers or fiberglass to resins
  • See VEE-005 for polymeric version
  • Reacts with enamines to give (E)-β:-silylenamines, which cross-couple with aryl iodides to give β-aryl enamines
  • Employed as a coupling agent, adhesion promoter, and crosslinking agent
  • Used in microparticle surface modification for fillers
  • Compatible with sulfur and peroxide cured rubber, polyester, polyolefin, styrene, and acrylic based materials
  • For vinylations
  • Available as an oligomeric hydrolysate, SIV9112.2
  • 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