PHENYLTRIMETHOXYSILANE, 99+%

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.

Aliphatic, fluorinated aliphatic or substituted aromatic hydrocarbon substituents are the hydrophobic entities which enable silanes to induce surface hydrophobicity. The organic substitution of the silane must be non-polar. The hydrophobic effect of the organic substitution can be related to the free energy of transfer of hydrocarbon molecules from an aqueous phase to a homogeneous hydrocarbon phase. A successful hydrophobic coating must eliminate or mitigate hydrogen bonding and shield polar surfaces from interaction with water by creating a non-polar interphase. Although silane and silicone derived coatings are in general the most hydrophobic, they maintain a high degree of permeability to water vapor. This allows coatings to breathe and reduce deterioration at the coating interface associated with entrapped water. Since ions are not transported through non-polar silane and silicone coatings, they offer protection to composite structures ranging from pigmented coatings to rebar reinforced concrete. A selection guide for hydrophobic silanes can be found on pages 22-31 of the Hydrophobicity, Hydrophilicity and Silane Surface Modification brochure.

Viscosity, 25 °C: 2.1 cSt

Vapor pressure, 108 °: 20 mm

Dipole moment: 1.77

Dielectric constant: 4.44

Cross-couples w/ aryl bromides w/o fluoride and w/ NaOH

High yields w/ Pd and carbene ligands

Cross-coupled in presence of aryl aldehyde

Undergoes 1,4-addition to enones. 1,2- and 1,4-addition to aldehyde undergoes coupling and asymmetric coupling w/ α-bromoesters

Reacts with 2° amines to give anilines

N-arylates nitrogen heterocycles

Cross-coupled w/ alkynyl bromides and iodides

Intermediate for high temperature silicone resins

Hydrophobic additive to other silanes with excellent thermal stability

Cross couples with aryl halides

Phenylates heteroaromatic carboxamides

Directly couples with primary alkyl bromides and iodides

Converts arylselenyl bromides to arylphenylselenides

Used in nickel-catalyzed direct phenylation of C-H bonds in heteroaromatic systems, benzoxazoles

Immobilization reagent for aligned metallic single wall nanotubes (SWNT)

Standard grade available, SIP6822.0

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