Silanes

Tri-substituted Silane Reducing Agent Organosilanes are hydrocarbon-like and possess the ability to serve as both ionic and free-radical reducing agents. These reagents and their reaction by-products are safer and more easily handled and disposed than many other reducing agents. The metallic nature of silicon and its low electronegativity relative to hydrogen lead to polarization of the Si-H bond yielding a hydridic hydrogen and a milder reducing agent compared to aluminum-, boron-, and other metal-based hydrides. A summary of some key silane reductions are presented in Table 1 of the Silicon-Based Reducing Agents brochure. Triphenylsilane; Triphenylsilanlyl hydride More effective radical-based reagent for reduction of organic halides than the trialkylsilanesCompares well with tri-n-butyltin hydride in reduction of enones to ketonesShows good selectivity in the reduction of cyclic hemiacetalsConverts O-acetyl furanoses and pyranoses to deoxy sugarsExtensive review of silicon based reducing agents: Larson, G.; Fry, J. L. "Ionic and Organometallic-Catalyzed Organosilane Reductions", Wipf, P., Ed.; Wiley, 2007

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. Dimethyldiacetoxysilane; Diacetoxydimethylsilane Reagent for the preparation of cis-diols and corticosteroids

Bis[m-(2-triethoxysilylethyl)tolyl]polysulfide Sulfur functional dipodal silaneDark, viscous liquid Coupling agent for styrene-butadiene rubber, SBR

Aromatic 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. Phenethyldimethyl(dimethylamino)silane; N,N,1,1-Tetramethyl-1-(2-phenylethyl)silanamine; N,N,1,1-Tetramethyl-1-(2-phenylethyl)-silanamine Contains 10-15% α-isomer

N,N-didecyl-N-methyl-N-(3-trimethoxysilylpropyl)ammonium chloride; (trimethoxysilylpropyl)didecylmethylammonium chloride; didecylmethyl[3-(trimethoxysilyl)propyl]ammonium chloride Quaternary amino functional trialkoxy silaneIn combination with TEOS (SIT7110.0), forms high pore volume xerogels with adsorptive capacityContains 3-5% Cl(CH2)3Si(OMe)340-42% in methanol

Olefin 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. Dipodal 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. 1,2-Bis(triethoxysilyl)ethylene; 4,4,7,7-Tetraethoxy-3,8-dioxa-4,7-disiladec-5-ene ~80% trans isomerForms ethylene-bridged mesoporous silicas

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. 1,2-Bis(trimethoxysilyl)decane; 3,3,6,6-Tetramethoxy-4-octyl-2,7-dioxa-3,6-disilaoctane Pendant dipodal silaneEmployed in high pH HPLCEmployed in the fabrication of luminescent molecular thermometers

DMS-S51 - Silanol terminated polydimethylsiloxane cSt 90,000-150,000

N-(Trimethoxysilylpropyl)ethylenediaminetriacetate, tripotassium salt; trihydroxysilylpropyl edta, potassium salt; glycine, N-[2- [bis(carboxymethyl)-aminoethyl]-N-[3-(trihydroxysilyl)propyl-, potassium salt Carboxylate functional trialkoxyl silaneEssentially silanetriol, contains KClChelates metal ions30% in water

Tetramethylsilane; 4MS; TMS NMR gradeViscosity: 0.4 cSt?Hcomb: 3,851 kJ/mol?Hform: -232 kJ/mol?Hvap: 26.8 kJ/mol?Hfus: 6.7 kJ/molPhotoionization threshold: 8.1 eVCe: 1.838 x 10-3Vapor pressure, 20 °C: 589 mmCritical temperature: 185 °CCritical pressure: 33 atmHeat capacity: 195.2 Jmol-1K-1Dielectric constant: 1.92Intermediate for ?-SiC:H thin films by PECVD

N-Methylaminopropyltrimethoxysilane, 3-(trimethoxysilyl)-n-methyl-1-propanamine Secondary amino functional trialkoxy silaneγc of treated surfaces: 31 mN/mpKb 25H2O: 5.18Used in microparticle surface modificationCoupling agent for UV cure and epoxy systemsOrients liquid crystalsReacts with urethane prepolymers to form moisture-curable resins

Mono-substituted Silane Reducing Agent Organosilanes are hydrocarbon-like and possess the ability to serve as both ionic and free-radical reducing agents. These reagents and their reaction by-products are safer and more easily handled and disposed than many other reducing agents. The metallic nature of silicon and its low electronegativity relative to hydrogen lead to polarization of the Si-H bond yielding a hydridic hydrogen and a milder reducing agent compared to aluminum-, boron-, and other metal-based hydrides. A summary of some key silane reductions are presented in Table 1 of the Silicon-Based Reducing Agents brochure. Trihydridosilane Silyl Hydrides are a distinct class of silanes that behave and react very differently than conventional silane coupling agents. They react with the liberation of byproduct hydrogen. Silyl hydrides can react with hydroxylic surfaces under both non-catalyzed and catalyzed conditions by a dehydrogenative coupling mechanism. Trihydridosilanes react with a variety of pure metal surfaces including gold, titanium, zirconium and amorphous silicon, by a dissociative adsorption mechanism. The reactions generally take place at room temperature and can be conducted in the vapor phase or with the pure silane or solutions of the silane in aprotic solvents. Deposition should not be conducted in water, alcohol or protic solvents. n-Octylsilane; 1-Sila-nonane Fugitive inhibitor of hydrosilylationForms SAMs on titanium, gold and silicon surfacesExtensive review of silicon based reducing agents: Larson, G.; Fry, J. L. "Ionic and Organometallic-Catalyzed Organosilane Reductions", Wipf, P., Ed.; Wiley, 2007

N-(3-trimethoxysilylpropyl)perfluorohexanamide; 2,2,3,3,4,4,5,5,6,6,6-undecafluoro-N-[3-(trimethoxysilyl)propyl]hexanamide Specialty amine functional trialkoxy silaneContact angle, water on treated silica surface: 105-110°γc of treated surfaces: 20.6 mN/m

Trimethylsilyl Blocking Agent Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure. 1- Methoxy-1-trimethysiloxy-2-methyl-1-propene; Methyl(trimethylsilyl)dimethylketene acetal; 1-Methoxy-2-methyl-1-(trimethylsiloxy)propene Used for silylation of acids, alcohols, thiols, amides and ketonesNafion SAC-13 has been shown to be a recyclable catalyst for the trimethylsilylation of primary, secondary, and tertiary alcohols in excellent yields and short reaction timesSummary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure

Trialkylsilyl Blocking Agent Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure. 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. 3,3-Dimethylbutyldimethylchlorosilane; Neohexyldimethylchlorosilane Sterically hindered neohexylchlorosilane protecting groupBlocking agent, forms bonded phases for HPLCSummary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure

Trialkylsilyl Blocking Agent Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure. 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. n-Butyldimethyl(dimethylamino)silane; Trimethylsilyldimethylamine Reactive aminofunctional organosilaneHighly reactive reagent for bonded phases without acidic byproductSummary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure

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 cStCopolymerization parameters- e,Q: -0.38, 0.031Specific wetting surface area: 528 m2/gVapor pressure, 20 °C: 9 mmEmployed in two-stage and one-stage graft polymerization/crosslinking for polyethylene (PE)Copolymerizes with ethylene to form moisture crosslinkable polymersConverts arylselenyl bromides to arylvinylselenidesReacts with anhydrides to transfer both vinyl and methoxy and thus form the mixed diesterCross-couples with α-bromo esters to give α-vinyl esters in high eeUsed in microparticle surface modificationFor vinylationsAlkenyltrialkoxysilanes react w/ aryl bromides and iodides to form styrenes under fluoride- and ligand-free and aqeous conditionsReacts in presence of fluorideExtensive 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