2996-92-1

Basic information

• Product Name: Phenyltrimethoxysilane
• Synonyms: Benzene, (triMethoxysilyl)-;Trimethoxyphenylsilane >=94%;Trimethoxyphenylsilane deposition grade, 98%;A 153;CP0330;phenyltrimethoxy-silan;Silane, phenyltrimethoxy-;trimethoxyphenyl-silan
• CAS NO: 2996-92-1
• Molecular Formula: C₉H₁₄O₃Si
• Molecular Weight: 198.29
• EINECS: 221-066-9
• Product Categories: NULL;silane;Functional Materials;Si (Classes of Silicon Compounds);Silane Coupling Agents;Silane Coupling Agents (Intermediates);Si-O Compounds;Trialkoxysilanes;Phenyl Silanes;organosilicon compounds
• Mol File: 2996-92-1.mol

Chemical Properties

• Melting Point: -25°C
• Boiling Point: 233 °C(lit.)
• Flash Point: 99 °F
• Appearance: colorless/liquid
• Density: 1.062 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.944mmHg at 25°C
• Refractive Index: n20/D 1.468(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• BRN: 2937896
• CAS DataBase Reference: Phenyltrimethoxysilane(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyltrimethoxysilane(2996-92-1)
• EPA Substance Registry System: Phenyltrimethoxysilane(2996-92-1)

Safety Data

• Hazard Codes: T,Xi,Xn
• Statements: 10-36/37/38-68/20/21/22-20/21/22-14
• Safety Statements: 7-16-26-36/37-45-37/39-36
• RIDADR: UN 1992 3/PG 3
• WGK Germany: 3
• RTECS: VV5252000
• F: 10-21
• TSCA: Yes
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 2996-92-1(Hazardous Substances Data)

Usage

Uses

Phenyltrimethoxysilane is used as a crosslinking agent for silicone resin and to produce polymer organic silicon compounds. This enhances the properties of the materials and contributes to their overall performance.
Used in Nanoelectronics and Material Science Research:
Phenyltrimethoxysilane is used as an organosilicate compound in the field of nanoelectronics and material science research. Its unique properties make it a valuable component in the development of advanced materials and devices.
Used in the Preparation of Polytrimethoxyphenylsilane (PTMS):
Phenyltrimethoxysilane is used in the preparation of PTMS, which facilitates the removal of graphene after chemical vapor deposition (CVD). This application is crucial in the production of high-quality graphene for various electronic and industrial applications.
Used in the Fabrication of Localized Surface Plasmon Resonance (LSPR) Sensors:
Phenyltrimethoxysilane is also used in the synthesis of molecularly imprinted sol-gel materials for the fabrication of LSPR sensors. These sensors have potential applications in various fields, including environmental monitoring, medical diagnostics, and chemical sensing.

Flammability and Explosibility

Flammable

Purification Methods

Fractionate it through an efficient column but note that it forms an azeotrope with MeOH which is a likely impurity. [Kantor J Am Chem Soc 75 2712 1953 Beilstein 16 IV 1556.]

InChI:InChI=1/C9H14O3Si/c1-10-13(11-2,12-3)9-7-5-4-6-8-9/h4-8H,1-3H3

Upstream product

• 681-84-5 tetramethylorthosilicate 
• 67-56-1 methanol 
• 98-13-5 Phenyltrichlorosilane 
• 108-86-1 bromobenzene 
• 18544-45-1 dichlorodimethoxysilane 
• 538-86-3 benzyl methyl ether 
• 1634-04-4 tert-butyl methyl ether 
• 1016-09-7 benzhydryl methyl ether 
• 694-53-1 phenylsilane 
• 18246-06-5 chloro(dimethoxy)phenylsilane 
• 124-41-4 sodium methylate 
• 2996-92-1 phenyl trimethylsiloxane 
• 20699-69-8 [diphenylmanganese] 
• 79-20-9 acetic acid methyl ester 

Downstream Products

• 17146-71-3 tris-(2-dimethylamino-ethoxy)-phenyl-silane 
• 3047-74-3 phenylsilanetriol 
• 54824-83-8 1-phenyl-3,7,10-trimethylsilatrane 
• 2097-19-0 1-phenyl-2,8,9-trioxa-5-aza-1-silabicyclo{3.3.3}undecane 
• 1015-10-7 tert-butyl-dimethoxy-phenylsilane 
• 17146-69-9 Tris-<2-amino-ethoxy>-phenyl-silan 
• 131120-91-7 8-(dimethylamino)-1-naphthyldi(methoxy)phenylsilane 
• 6157-41-1 sodium bis(benzene-1,2-diolatophenyl)silicate 
• 1657-55-2 1,2-bis(4-methoxyphenyl)ethane 
• 109658-84-6 Dimethoxy(4-methoxybenzyl)phenylsilan 
• 104892-79-7 (Dimethoxy-trimethylsilanylethynyl-silanyl)-benzene 
• 2050-68-2 4,4'-dichlorobiphenyl 
• 2051-62-9 4'-biphenyl chloride 
• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 

Relevant articles and documents

Low-valent iron(I) amido olefin complexes as promotors for dehydrogenation reactions

FeI compounds including hydrogenases show remarkable properties and reactivities. Several iron(I) complexes have been established in stoichiometric reactions as model compounds for N2 or CO2 activation. The development of well-defined iron(I) complexes for catalytic transformations remains a challenge. The few examples include cross-coupling reactions, hydrogenations of terminal olefins, and azide functionalizations. Here the syntheses and properties of bimetallic complexes [MFeI(trop2dae)(solv)] (M=Na, solv=3-thf; M=Li, solv=2-Et2O; trop=5H-dibenzo[a,d]cyclo-hepten-5-yl, dae=(N-CH2-CH2-N) with a d7 Fe low-spin valence-electron configuration are reported. Both compounds promote the dehydrogenation of N,N-dimethylaminoborane, and the former is a precatalyst for the dehydrogenative alcoholysis of silanes. No indications for heterogeneous catalyses were found. High activities and complete conversions were observed particularly with [NaFeI(trop2dae)(thf)3]. Square-planar FeI: A low-valent iron center has been stabilized in a distorted square-planar coordination geometry by using a diamido-diolefin ligand and an alkali metal counterion (see scheme). The heterobimetallic compounds of this type initiate the dehydrogenation of N,N-dimethylaminoborane and the dehydrogenative alcoholysis of silanes. The counterion [Li(OEt2)2]+ or [Na(thf)3]+ affects the catalytic performance.

A triazine-based covalent organic framework/palladium hybrid for one-pot silicon-based cross-coupling of silanes and aryl iodides

A triazine-based covalent organic framework (COF-SDU1) was synthesized through facile solvothermal conditions and characterized by IR, solid state 13C NMR, XRD, elemental analysis and BET. By a simple solution infiltration method, Pd(ii) species were successfully immobilized into COF-SDU1 due to its two-dimensional eclipsed layer-sheet structure and nitrogen-rich content. High-resolution TEM images showed the uniform loading of the Pd species into the COF-SDU1 matrix. By using this hybrid material, Pd(ii)/COF-SDU1, as a sustainable and green catalyst, one-pot cross-coupling of silanes and aryl iodides was realized with high selectivity. The catalyst can be easily recovered by a simple separation process and recycled several times without obvious loss of activity and selectivity.

Hydrosilane σ-Adduct Intermediates in an Adaptive Zinc-Catalyzed Cross-dehydrocoupling of Si?H and O?H Bonds

Three-coordinate PhBOX (Formula presented.) ZnR (PhBOX (Formula presented.) =phenyl-(4,4-dimethyl-oxazolinato; R=Me: 2 a, Et: 2 b) catalyzes the dehydrocoupling of primary or secondary silanes and alcohols to give silyl ethers and hydrogen, with high turnover numbers (TON; up to 107) under solvent-free conditions. Primary and secondary silanes react with small, medium, and large alcohols to give various degrees of substitution, from mono- to tri-alkoxylation, whereas tri-substituted silanes do not react with MeOH under these conditions. The effect of coordinative unsaturation on the behavior of the Zn catalyst is revealed through a dramatic variation of both rate law and experimental rate constants, which depend on the concentrations of both the alcohol and hydrosilane reactants. That is, the catalyst adapts its mechanism to access the most facile and efficient conversion. In particular, either alcohol or hydrosilane binds to the open coordination site on the PhBOX (Formula presented.) ZnOR catalyst to form a PhBOX (Formula presented.) ZnOR(HOR) complex under one set of conditions or an unprecedented σ-adduct PhBOX (Formula presented.) ZnOR(H?SiR′3) under other conditions. Saturation kinetics provide evidence for the latter species, in support of the hypothesis that σ-bond metathesis reactions involving four-centered electrocyclic 2σ–2σ transition states are preceded by σ-adducts.

Charge Modified Porous Organic Polymer Stabilized Ultrasmall Platinum Nanoparticles for the Catalytic Dehydrogenative Coupling of Silanes with Alcohols

Developing an ideal stabilizer to prevent the aggregation of nanoparticles is still a big challenge for the practical application of noble metal nanocatalysts. Herein, we develop a charge (NTf2?) modified porous organic polymer (POP-NTf2) to stabilize ultrasmall platinum nanoparticles. The catalyst is characterized and applied in the catalytic dehydrogenative coupling of silanes with alcohols. The catalyst exhibits excellent catalytic performance with highly dispersed ultrasmall platinum nanoparticles (ca. 2.22?nm). Moreover, the catalyst can be reused at least five times without any performance significant loss and Pt NPs aggregation. Graphic Abstract: [Figure not available: see fulltext.]

N-Heterocyclic Carbene Complexes of Nickel, Palladium, and Iridium Derived from Nitron: Synthesis, Structures, and Catalytic Properties

The mesoionic compound (1,4-diphenyl-1,2,4-triazol-4-ium-3-yl)phenylazanide, commonly referred to as Nitron, has been employed as a "crypto-NHC"to afford 1,2,4-triazolylidene compounds of nickel, palladium, and iridium. Specifically, Nitron reacts with NiBr2, PdCl2, and [Ir(COD)Cl]2 to afford the N-heterocyclic carbene complexes (NitronNHC)2NiBr2, (NitronNHC)2PdCl2, and (NitronNHC)Ir(COD)Cl, respectively. The lattermost compound reacts with (i) CO to afford the dicarbonyl compound (NitronNHC)Ir(CO)2Cl and (ii) CO, in the presence of PPh3, to afford the monocarbonyl compound (NitronNHC)Ir(PPh3)(CO)Cl. Structural studies on (NitronNHC)Ir(COD)Cl and (NitronNHC)Ir(CO)2Cl indicate that NitronNHC has a stronger trans influence than does Cl; furthermore, IR spectroscopic studies on (NitronNHC)Ir(CO)2Cl indicate that NitronNHC is electronically similar to the structurally related Enders carbene but is less electron donating than imidazol-2-ylidenes with aryl substituents. Significantly, the NitronNHC ligand affords catalytic systems, as illustrated by the ability of (NitronNHC)Ir(CO)2Cl to effect (i) the dehydrogenation of formic acid, (ii) aldehyde hydrosilylation, (iii) dehydrocoupling of hydrosilanes and alcohols, and (iv) ketone reduction via transfer hydrogenation.

High Production of Hydrogen on Demand from Silanes Catalyzed by Iridium Complexes as a Versatile Hydrogen Storage System

The catalytic dehydrogenative coupling of silanes and alcohols represents a convenient process to produce hydrogen on demand. The catalyst, an iridium complex of the formula [IrCp?(Cl)2(NHC)] containing an N-heterocyclic carbene (NHC) ligand functionalized with a pyrene tag, catalyzes efficiently the reaction at room temperature producing H2 quantitatively within a few minutes. As a result, the dehydrogenative coupling of 1,4-disilabutane and methanol enables an effective hydrogen storage capacity of 4.3 wt % that is as high as the hydrogen contained in the dehydrogenation of formic acid, positioning the silane/alcohol pair as a potential liquid organic hydrogen carrier for energy storage. In addition, the heterogenization of the iridium complex on graphene presents a recyclable catalyst that retains its activity for at least 10 additional runs. The homogeneous distribution of catalytic active sites on the basal plane of graphene prevents diffusion problems, and the reaction kinetics are maintained after immobilization.

Environment-friendly preparation method of diphenyldimethoxysilane

The invention relates to a preparation method of phenyl alkoxysilane, which includes: dissolving phenyl chlorosilane in an organic solvent, adding alcohol-alkoxide solution and performing a reaction in an inert atmosphere; when the reaction is carried out to a certain degree, adding a sodium alkoxide solution, continuously carrying out the reaction; when the reaction is finished, distilling the reaction product to form the phenyl alkoxysilane.

Pollution-free method for preparing diphenyldiethoxysilane

The invention relates to a synthetic method of phenyl alkoxysilane, which includes: dissolving phenyl chlorosilane in an organic solvent, and adding an alcohol-alkoxide solution, performing a reactionin an inert atmosphere; when the reaction is carried out to a certain degree, adding a sodium alkoxide solution, continuously carrying out the reaction; when the reaction is finished, distilling thereaction product to form the phenyl alkoxysilane.

Dehydrogenative Coupling of Hydrosilanes and Alcohols by Alkali Metal Catalysts for Facile Synthesis of Silyl Ethers

Cross-dehydrogenative coupling (CDC) of hydrosilanes with hydroxyl groups, using alkali metal hexamethyldisilazide as a single-component catalyst for the formation of Si-O bonds under mild condition, is reported. The potassium salt [KN(SiMe3)2] is highly efficient and chemoselective for a wide range of functionalized alcohols (99% conversion) under solvent-free conditions. The CDC reaction of alcohols with silanes exhibits first-order kinetics with respect to both catalyst and substrate concentrations. The most plausible mechanism for this reaction suggests that the initial step most likely involves the formation of an alkoxide followed by the formation of metal hydride as active species.

Catalytic Dehydrogenative Coupling of Hydrosilanes with Alcohols for the Production of Hydrogen On-demand: Application of a Silane/Alcohol Pair as a Liquid Organic Hydrogen Carrier

The compound [Ru(p-cym)(Cl)2(NHC)] is an effective catalyst for the room-temperature coupling of silanes and alcohols with the concomitant formation of molecular hydrogen. High catalyst activity is observed for a variety of substrates affording quantitative yields in minutes at room temperature and with a catalyst loading as low as 0.1 mol %. The coupling reaction is thermodynamically and, in the presence of a Ru complex, kinetically favourable and allows rapid molecular hydrogen generation on-demand at room temperature, under air, and without any additive. The pair silane/alcohol is a potential liquid organic hydrogen carrier (LOHC) for energy storage over long periods in a safe and secure way. Silanes and alcohols are non-toxic compounds and do not require special handling precautions such as high pressure or an inert atmosphere. These properties enhance the practical applications of the pair silane/alcohol as a good LOHC in the automotive industry. The variety and availability of silanes and alcohols permits a pair combination that fulfils the requirements for developing an efficient LOHC.