Silanes

<p>Olefin Functional Alkoxy Silane<br>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.<br>Dipodal Silane<br>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.<br>1,2-Bis(triethoxysilyl)ethylene; 4,4,7,7-Tetraethoxy-3,8-dioxa-4,7-disiladec-5-ene<br>~80% trans isomerForms ethylene-bridged mesoporous silicas<br></p>

<p>Trimethylsilyl Blocking Agent<br>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.<br>1- Methoxy-1-trimethysiloxy-2-methyl-1-propene; Methyl(trimethylsilyl)dimethylketene acetal; 1-Methoxy-2-methyl-1-(trimethylsiloxy)propene<br>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<br></p>

<p>Siloxane-Based Silane Reducing Agent<br>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.<br>Phenyltris(dimethylsiloxy)silane; Phenyl hydride cross-linker; 3-[(Dimethylsilyl)oxy]-1,1,5,5-tetramethyl-3-phenyltrisiloxane<br>High molecular weight silane reducing agentCrosslinker for vinylphenylsilicone 2-component elastomersExtensive review of silicon based reducing agents: Larson, G.; Fry, J. L. "Ionic and Organometallic-Catalyzed Organosilane Reductions", Wipf, P., Ed.; Wiley, 2007<br></p>

<p>Non-functional Alkoxy Silane<br>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.<br>Dipodal Silane<br>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.<br>Alkyl Silane - Dipodal Surface Bonding<br>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.<br>1,2-Bis(trimethoxysilyl)ethane; 3,3,6,6-Tetramethoxy-2,7-dioxa-3,6-disilaoctane<br>Caution: Inhalation HazardAir Transport ForbiddenVapor pressure, 20 °C: 0.08 mmEmployed in fabrication of multilayer printed circuit boards<br></p>

<p>Alkynylsilane Cross-Coupling Agent<br>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.<br>1-Trimethylsilylpropyne; Propynyltrimethylsilane; 1-(Trimethylsilyl)prop-1-yne<br>Forms polymers with very high oxygen permeabilityUseful in Sonogashira reactionsPolymerization catalyzed with TaCl5/(C6H5)3BiConverts aldehydes to 1,3-dienes in presence of Cp2Zr(H)ClUsed in the preparation of alkynylxenon fluoridePolymeric version available, SSP-070Extensive 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<br></p>

<p>3-Chloropropylmethyldiethoxysilane; methyldiethoxy(chloropropyl)silane; (3- chloropropyl)diethoxymethylsilane; 1-chloro-3-(methyldiethoxysilyl)propane<br>Halogen functional dialkoxy silaneIntermediate for functional silicone polymers<br></p>

<p>bis(3-trimethoxysilylpropyl)-N-methylamine; N-methylaminobis(propyltrimethoxysilane)<br>Tertiary amino functional dipodal silaneDipodal analog of SIM6500.0<br></p>

<p>Alkyl Silane - Conventional Surface Bonding<br>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.<br>ω-Butylpoly(dimethylsiloxanyl)ethyltriethoxysilane; α-Butyl-ω-triethoxysilylethyl terminated polydimethylsiloxane<br>5-8 (Me2SiO)Hydrophobic surface treatment<br></p>

<p>Ester Functional Trialkoxy Silane<br>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.<br>Hydrophilic Silane - Polar - Hydrogen Bonding<br>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.<br>2-[(Acetoxy(polyethyleneoxy)propyl]triethoxysilane; (Triethoxysilylpropylpolyethylene oxide)acetate<br>Viscosity: 50 cStFunctional PEG Silane (500-700 g/mol)PEO, Ester, Triethoxysilane termination utilized for hydrophilic surface modificationDual functional PEGylation reagentHydrogen bonding hydrophilic silaneUsed in microparticle surface modification<br></p>

<p>Alkyl Silane - Conventional Surface Bonding<br>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.<br>n-Decyltrichlorosilane; Trichlorosilyldecane; Trichlorodecylsilane<br></p>

<p>Dialkyl Silane Reducing Agent<br>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.<br>Diphenylsilane; Dihydridodiphenylsilane<br>Converts amides to aldehydes in combination with Ti(OiPr)4Used in the preparation of silyl-substituted alkylidene complexes of tantalumUsed in the ionic reduction of enones to saturated ketonesUsed in the reductive cyclization of unsaturated ketonesReduces esters in the presence of zinc hydride catalystSilylates 1,2-diols in presence of tris(pentafluorophenyl)boraneReduces α-halo ketones in presence of Mo(0)Used in enantioselective reduction of iminesReduces thio esters to ethersSelective reduction of estersReduces esters to alcohols with Rh catalysisEmployed in the asymmetric reduction of methyl ketones and other ketonesReductively cleaves allyl acetatesExtensive review of silicon based reducing agents: Larson, G.; Fry, J. L. "Ionic and Organometallic-Catalyzed Organosilane Reductions", Wipf, P., Ed.; Wiley, 2007<br></p>

<p>Phenyl-Containing Blocking Agent<br>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.<br>Tri-substituted Silane Reducing Agent<br>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.<br>Phenyldimethylsilane; Dimethylphenylsilane;<br>Vapor pressure, 25 °C: 4 mmReacts with alcohols in presence of Wilkinson’s catalystUsed to prepare α-phenyldimethylsilyl esters with high enantioselectivityYields optically active reduction products with chiral Rh or Pd catalystsUndergoes 1,4-addition to pyridines forming N-silylated dihydropyridinesUsed in the fluoride ion-catalyzed reduction of aldehydes and ketones, and α-substituted alkanones to threo productsHydrosilylation of 1,4-bis(trimethylsilyl)butadiyne can go to the trisilyl allene or the trisilyl enyneErythro reduction of α-substituted alkanones to diols and aminoethanolsUsed to reduce α-amino ketones to aminoethanols with high stereoselectivityTogether with CuCl reduces aryl ketones, but not dialkyl ketonesUsed in the silylformylation of acetylenesExcellent reducing agent for the reduction of enones to saturated ketonesShows better selectivity than LAH in the reduction of oximes to alkoxyamines.Extensive review of silicon based reducing agents: Larson, G.; Fry, J. L. "Ionic and Organometallic-Catalyzed Organosilane Reductions", Wipf, P., Ed.; Wiley, 2007Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure<br></p>

<p>2-(2-Pyridylethyl)trimethoxysilane, 2-(trimethoxysilylethyl)pyridine<br>Monoamino functional trialkoxy silaneUsed in microparticle surface modification<br></p>

<p>Hexamethylcyclotrisiloxane (HMCTS, D3)<br>Undergoes ring-opening anionic polymerizationReacts with three equivalents of an organolithium reagent to give derivatized dimethylsilanols<br></p>

<p>Diamino Functional Trialkoxy Silane<br>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.<br>N-(6-Aminohexyl)aminomethyltriethoxysilane; N-[6-Triethoxysilyl)methyl]hexamethylethylenediamine<br>Primary amine and an internal secondary amine coupling agent for UV cure and epoxy systemsUsed in microparticle surface modification<br></p>

<p>Volatile Higher Silane<br>Volatile higher silanes are low temperature, high deposition rate precursors. By appropriate selection of precursor and deposition conditions, silicon deposition can be shifted from amorphous hydrogenated silicon toward microcrystalline silicon structures. As the number of silicon atoms increases beyond two, electrons are capable of sigma–sigma bond conjugation. The dissociative adsorption of two of the three hydrogen atoms on terminal silicon atoms has a lower energy barrier.<br>Isotetrasilane; (Trisilyl)silane; 2-Silyltrisilane<br>PYROPHORICAIR TRANSPORT FORBIDDEN?Hvap: 32.5 kJ/molPrecursor for low temp. epitaxy of doped crystalline siliconEmployed in low temperature CVD of amorphous silicon<br></p>

<p>Trialkylsilyl Blocking Agent<br>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.<br>N,N-Dimethylaminotriethylsilane; Triethylsilyldimethylamine<br>Very reactive triethylsilyl protecting groupDimethylamine by-product producedUsed primarily for the protection of alcoholsCan be used to protect amines and carboxylic acidsSummary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure<br></p>

<p>Aldehyde Functional Trialkoxy Silane<br>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.<br>Triethoxysilylundecanal<br>Treated surface contact angle, water: 70°Long chain coupling agent for DNAProvides greater stability for coupled proteins than shorter alkyl homologsLong chain homolog of triethoxysilylbutyraldehyde (SIT8185.3)<br></p>

<p>Alkyl Silane - Conventional Surface Bonding<br>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.<br>n-Octyltrimethoxysilane; Trimethoxysilyloctane<br>Viscosity: 1.0 cStVapor pressure, 75 °: 0.1 mmTreatment for particles used in non-aqueous liquid dispersionsTrialkoxy silane<br></p>

<p>Tipped PEG Silane (363.83 g/mol)<br>PEO, Trichlorosilane termination utilized for hydrophilic surface modificationDual functional PEGylation reagentForms self-assembled monolayers with "hydrophilic tips"Hydrogen bonding hydrophilic silane<br>Related Products<br>SIM6493.3: 2-[METHOXY(TRIETHYLENEOXY)]- (11-TRIETHOXYSILYL)UNDECANOATE, tech-95<br></p>