Silanes

<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>Hexyltrimethoxysilane; Trimethoxyhexylsilane; Trimethoxysilylhexane<br>Surface modification of TiO2 pigments improves dispersionTrialkoxy silane<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>Aromatic 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>Phenyldimethylchlorosilane; Chlorodimethylphenylsilane; Dimethylphenylchlorosilane<br>Viscosity: 1.4 cStΔHvap: 47.7 kJ/molVapor pressure, 25 °: 1 mmForms cuprateUsed in analytical proceduresSummary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure<br></p>

<p>Methacrylate 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>O-(Methacryloxyethyl)-N-(triethoxysilylpropyl)carbamate<br>Coupling agent for UV cure systemsHydrophilic monomerUsed in microparticle surface modificationInhibited with MEHQ<br></p>

<p>(3- Glycidoxypropyl)trimethoxysilane; 3-(2,3-epoxypropoxy)propyltrimethoxysilane; trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane; 3-(trimethoxysilyl)propyl glycidyl ether; GLYMO<br>Epoxy functional trialkoxy silaneViscosity: 3.2 cStγc of treated surfaces: 38.55 mN/mSpecific wetting surface area: 331 m2/gComponent in aluminum metal bonding adhesivesCoupling agent for epoxy composites employed in electronic "chip" encapsulationComponent in abrasion resistant coatings for plastic opticsUsed to prepare epoxy-containing hybrid organic-inorganic materialsUsed in microparticle surface modificationEpoxy silane treated surfaces convert to hydrophilic-diols when exposed to moisture<br></p>

<p>Azide 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>11-Azidoundecyltrimethoxysilane, 11-(trimethoxysilyl)undecyl azide<br>Coupling agent for surface modificationUsed in "click" chemistryAVOID CONTACT WITH METALS<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>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>Dimethylaminotrimethylsilane; Pentamethylsilanamine; Trimethylsilyldimethylamine; TMSDMA<br>ΔHvap: 31.8 kJ/molSelectively silylates equatorial hydroxyl groups in prostaglandin synthesisStronger silylation reagent than HMDS; silylates amino acidsDialkylaminotrimethylsilanes are used in the synthesis of pentamethinium saltsWith aryl aldehydes converts ketones to α,β-unsaturated ketonesSimilar to SID6110.0 and SID3398.0Liberates Me2NH upon reactionSilylates urea-formaldehyde polycondensatesSilylates phosphorous acidsNafion 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>N-Methylaminopropyltrimethoxysilane, 3-(trimethoxysilyl)-n-methyl-1-propanamine<br>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<br></p>

<p>(3-Glycidoxypropyl)triethoxysilane; triethoxy[3-(oxiranylmethoxy)propyl]-silane; 2-[[3- (triethoxysilyl)propoxy]methyl]-oxirane; triethoxy[3- (oxiranylmethoxy)propyl]silane; 3-(2,3- epoxypropoxypropyl)triethoxysilane<br>Epoxy functional trialkoxy silaneViscosity: 3 cSt Coupling agent for latex polymersUsed in microparticle surface modificationPrimer for aluminum and glass to epoxy coatings and adhesives when applied as a 1-2% solution in solventCoupling agent for UV cure and epoxy systemsEpoxy silane treated surfaces convert to hydrophilic-diols when exposed to moisture<br></p>

<p>Diolefin Functional Amino 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>DVTMDZ; Bis(vinyldimethylsilyl)amine; N-(Dimethylvinylsilyl)-1,1-dimethyl-1-vinylsilylamine; 1,1,3,3-Tetramethyl-1,3-divinyldisilazane<br>Adhesion promoter for negative photoresistsFor silylation of glass capillary columnsCopolymerizes with ethylene<br></p>

<p>2-Hydroxy-4-(3-triethoxysilylpropoxy)diphenylketone; 4-(3-triethoxysilylpropoxy)-2-hydroxybenzophenone [2-hydroxy-4-[3-(triethoxysilyl)propoxy]phenyl]phenylmethanone<br>UV active trialkoxy silaneAmber liquidViscosity, 25 °C: 125-150 cStUV max: 230, 248, 296 (s), 336Strong UV blocking agent for optically clear coatings,Absorbs from 210-420 nmUsed in Bird-deterrent Glass Coatings<br></p>

<p>N-Phenylaminopropyltrimethoxysilane; N-[3-(trimethoxysilyl)propyl]aniline; [3-(trimethoxysilyl)propyl]aniline<br>Secondary amino functional trialkoxy silaneSpecific wetting surface: 307 m2/gCoupling agent for UV cure and epoxy systemsOxidatively stable coupling agent for polyimides, phenolics, epoxiesUsed in microparticle surface modification<br></p>

<p>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>Triethoxysilane; Silicon triethoxide; Triethoxysilylhydride<br>CAUTION: VAPORS CAUSE BLINDNESS — GOGGLES MUST BE WORNDISPROPORTIONATES IN PRESENCE OF BASE TO PYROPHORIC PRODUCTSContains trace Si–Cl for stabilityΔHcomb: -4,604 kJ/molΔHform: 925 kJ/molΔHvap: 175.4 kJ/molSurface tension: 22.3 mN/mVapor pressure, 20 °C: 20.2 mmCritical temperature: 244 °CDipole moment: 1.78 debyeHydrosilylates olefins in presence of PtUsed to convert alkynes to (E)–alkenes via hydrosilylation-desilylationReduces amides to amines in the presence of Zn(OAc)2Used in the reduction of phosphine oxides to phosphinesReduces esters in the presence of zinc hydride catalystReduces aldehydes and ketones to alcohols via the silyl ethers in presence of fluoride ionGives 1,2 reduction of enones to allyl alcoholsExtensive 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>Tipped PEG Silane (591-723 g/mol)<br>PEO, Trimethoxysilane termination utilized for hydrophilic surface modificationPEGylation reagentHydrogen bonding hydrophilic silane<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>Trimethylsilyltrifluoromethanesulfonate; Trimethylsilyltriflate; TMSOTf<br>Strong silylating agent for C- or O-silylationsReacts with nitroalkanes to give N,N-bis(trimethylsiloxy)enaminesNafion 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>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>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>tert-Butyldimethylchlorosilane; TBS-Cl; Chlorodimethyl-t-butylsilane; tert-Butylchlorodimethylsilane; Chloro(1,1-dimethylethyl)dimethylsilane<br>Excellent for 1° and 2° alcoholsSilylation catalyzed by imidazoleBlocking agent widely used in prostaglandin synthesisStable to many reagentsCan be selectively cleaved in presence of acetate, THP and benzyl ethers among othersUsed for the protection of alcohols, amines, thiols, lactams, and carboxylic acidsClean NMR characteristics of protecting groupSilylation reagent - derivatives resistant to Grignards, alkyl lithium compounds, etcFacile removal with flouride ion sourcesSummary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure<br></p>