Silanes

Arylsilane 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. Aromatic Hydrophobic Trialkoxy Silane 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. Phenyltrimethoxysilane; Trimethoxysilylbenzene Viscosity, 25 °C: 2.1 cStVapor pressure, 108 °: 20 mmDipole moment: 1.77Dielectric constant: 4.44Cross-couples w/ aryl bromides w/o fluoride and w/ NaOHHigh yields w/ Pd and carbene ligandsCross-coupled in presence of aryl aldehydeUndergoes 1,4-addition to enones. 1,2- and 1,4-addition to aldehyde undergoes coupling and asymmetric coupling w/ α-bromoestersReacts with 2° amines to give anilinesN-arylates nitrogen heterocyclesCross-coupled w/ alkynyl bromides and iodidesIntermediate for high temperature silicone resinsHydrophobic additive to other silanes with excellent thermal stabilityCross couples with aryl halidesPhenylates heteroaromatic carboxamidesDirectly couples with primary alkyl bromides and iodidesConverts arylselenyl bromides to arylphenylselenidesUsed in nickel-catalyzed direct phenylation of C-H bonds in heteroaromatic systems, benzoxazolesImmobilization reagent for aligned metallic single wall nanotubes (SWNT)Standard grade available, SIP6822.0Extensive 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

Alkyl Silane - Dipodal Surface Bonding 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. Non Functional Alkoxy 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. Dipodal Silane Dipodal silanes are a series of adhesion promoters that have intrinsic hydrolytic stabilities up to ~10,000 times greater than conventional silanes and are used in applications such as plastic optics, multilayer printed circuit boards and as adhesive primers for ferrous and nonferrous metals. They have the ability to form up to six bonds to a substrate compared to conventional silanes with the ability to form only three bonds to a substrate. Many conventional coupling agents are frequently used in combination with 10-40% of a non-functional dipodal silane, where the conventional coupling agent provides the appropriate functionality for the application, and the non-functional dipodal silane provides increased durability. Also known as bis-silanes additives enhance hydrolytic stability, which impacts on increased product shelf life, ensures better substrate bonding and also leads to improved mechanical properties in coatings as well as composite applications. Bis(triethoxysilyl)methane; 4,4,6,6-tetraethoxy-3,7-dioxa-4,6-disilanonane Intermediate for sol-gel coatings, hybrid inorganic-organic polymersForms methylene-bridged mesoporous structuresForms modified silica membranes that separate propylene/propane mixtures

Alkyl Silane - Conventional Surface Bonding 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. Cyclohexyltrichlorosilane; Trichlorosilylcyclohexane; trichloro(cyclohexyl)silane; Trichlorosilylcyclohexane Intermediate for melt-processable silsesquioxane-siloxanesEmployed in solid-phase extraction columns

Alkynylsilane 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. Bis(trimethylsilyl)acetylene; Bis(trimethylsilyl)ethyne Useful in Sonogashira cross-coupling reactionsVersatile reagent for introducing unsaturationUsed to prepare 1,2-bis(aryl)acetylenesReacts with internal acetylenes to form 1,2,4,5-tetrasubstituted benzenesUsed to prepare 4-alkynylthiazolesExtensive 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