2553-19-7

Basic information

• Product Name: Diphenyldiethoxysilane
• Synonyms: Diphenyldiethoxysilicane;Diethoxydiphenylsilane,97%;Diethoxydiphenylsilane,98%;Diphenyldiethoxysilane,min.97%;Diphenyldiethoxysilane, min. 97%;Diethoxydiphenylsilane,Diphenyldiethoxysilane;DPDES;DIPHENYLDIETHOXYSILANE
• CAS NO: 2553-19-7
• Molecular Formula: C₁₆H₂₀O₂Si
• Molecular Weight: 272.41
• EINECS: 219-860-5
• Product Categories: Dialkoxysilanes;Si (Classes of Silicon Compounds);Si-O Compounds;Phenyl Silanes;silane
• Mol File: 2553-19-7.mol

Chemical Properties

• Boiling Point: 167 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colorless or yellowish transparent liquid
• Density: 1.033 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000584mmHg at 25°C
• Refractive Index: n20/D 1.525(lit.)
• Sensitive: Moisture Sensitive
• BRN: 2281302
• CAS DataBase Reference: Diphenyldiethoxysilane(CAS DataBase Reference)
• NIST Chemistry Reference: Diphenyldiethoxysilane(2553-19-7)
• EPA Substance Registry System: Diphenyldiethoxysilane(2553-19-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• Hazardous Substances Data: 2553-19-7(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Synthesis:
Diphenyldiethoxysilane is used as a reagent for the preparation of diphenylsilylene derivatives of diols by exchange. This application is particularly useful in the synthesis of various organic compounds.
2. Used in Analytical Chemistry:
In the field of analytical chemistry, Diphenyldiethoxysilane is used as a component in the development of a new diethoxydiphenylsilane-based solid-phase microextraction fiber. This fiber is designed to extract trace levels of polycyclic aromatic hydrocarbons in milk and human urine, as well as detect explosives and explosive taggants such as 2,4,5-trinitrotoluene, 2,4-dinitrotoluene, 2,4-dinitrotoluence, and ethylene glycol dinitrate.
3. Used in Surface Modification:
Diphenyldiethoxysilane serves as an alkylsilylation reagent for the surface modification of nanoporous rice husk silica (RHS). This modification enhances the properties of RHS, making it suitable for various applications in different industries.

InChI:InChI=1/C16H20O2Si/c1-3-17-19(18-4-2,15-11-7-5-8-12-15)16-13-9-6-10-14-16/h5-14H,3-4H2,1-2H3

Upstream product

• 78-10-4 tetraethoxy orthosilicate 
• 4667-38-3 dichlorodiethoxysilane 
• 312-40-3 difluorodiphenylsilane 
• 555-75-9 aluminum ethoxide 
• 591-51-5 phenyllithium 
• 64-17-5 ethanol 
• 80-10-4 diphenylsilyl dichloride 
• 1623-99-0 phenyl sodium 
• 108-88-3 toluene 
• 775-12-2 diphenylsilane 
• 74-96-4 ethyl bromide 
• 108-90-7 chlorobenzene 
• 26138-28-3 phenylytterbium iodide 
• 998-30-1 Triethoxysilane 

Downstream Products

• 18733-69-2 ph2Si(ph-4-Cl)2 
• 775-12-2 diphenylsilane 
• 312-40-3 difluorodiphenylsilane 
• 80-10-4 diphenylsilyl dichloride 
• 13320-38-2 diphenyldibutoxysilane 
• 34690-92-1 C₂₂H₃₆O₆Si₃ 
• 55275-13-3 C₂₆H₂₄N₄O₂Si 
• 71573-88-1 2-(2,2-diphenyl-[1,3,6,2]dioxazasilocan-6-yl)-ethanol 
• 71573-85-8 2,2-diphenyl-1,3,6,2-trioxosiloxane 
• 66583-27-5 2,2-diphenyl-6-methyl-1,3-dioxa-6-aza-2-silacyclooctane 
• 512-63-0 1,1,3,3,5,5-hexaphenylcyclotrisiloxane 
• 797-77-3 1,1,1,5,5,5-hexamethyl-3,3-diphenyltrisiloxane 
• 3809-28-7 octa-cyclohexyloctasilsesquioxane 
• 546-56-5 octaphenylcyclotetrasiloxane 

Relevant articles and documents

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.]

Mechanistic Studies on the Hexadecafluorophthalocyanine–Iron-Catalyzed Wacker-Type Oxidation of Olefins to Ketones**

The hexadecafluorophthalocyanine–iron complex FePcF16 was recently shown to convert olefins into ketones in the presence of stoichiometric amounts of triethylsilane in ethanol at room temperature under an oxygen atmosphere. Herein, we describe an extensive mechanistic investigation for the conversion of 2-vinylnaphthalene into 2-acetylnaphthalene as model reaction. A variety of studies including deuterium- and 18O2-labeling experiments, ESI-MS, and 57Fe M?ssbauer spectroscopy were performed to identify the intermediates involved in the catalytic cycle of the oxidation process. Finally, a detailed and well-supported reaction mechanism for the FePcF16-catalyzed Wacker-type oxidation is proposed.

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.

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.

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.

Metal-Free Ammonium Iodide Catalyzed Oxidative Dehydrocoupling of Silanes with Alcohols

An ammonium iodide catalyzed direct oxidative coupling of silanes with alcohols to give various alkoxysilane derivatives was discovered. tert -Butyl hydroperoxide proved to be an efficient oxidant for this transformation. Attractive features of this protocol include its transition-metal-free nature and the mild reaction conditions.

Chlorosilane alcoholysis acid removing agent and regeneration method thereof

The invention discloses a chlorosilane alcoholysis acid removing agent and a regeneration method thereof. The regeneration method is characterized in that at a temperature of -10-130 DEG C, a substituting agent and an acid removing agent are added into a reactor in advance, chlorosilane is gradually added, the liquid phase obtained through filtration separation is subjected to rectification after the alcoholysis reaction is completed so as to obtain a silane finished product and the excessive substitution agent, the excessive substitution agent is recycled, and the acid removing agent obtained through filtration separation is recycled after being regenerated. According to the present invention, the yield of the silane prepared by using the process is more than or equal to 95%, and the recovery rate of the acid removing agent is more than or equal to 95%.

Nucleophilic attack of R-lithium at tetrahedral silicon in alkoxysilanes. An alternate mechanism

The currently accepted mechanism for nucleophilic attack at silicon in tetraalkoxysilanes, e.g. Si(OEt)4 is suggested to involve formation of penta- and then hexacoordinated intermediates as supported by the apparent exclusive formation of R3SiOR′ and R4Si from nucleophilic attack by RLi and RMgX. Our recent discovery of a direct route from biogenic silica to tetraalkoxyspirosiloxanes prompted us to revisit this reaction as a potential route to diverse silicon-containing species with single SiC bonds as early studies demonstrate that spirosiloxanes form quite stable pentacoordinated alkoxysilane compounds. As anticipated, Si(2-methyl-2,4-pentanediolato)2 (SP) reacts with RLi (R = Ph, anthracene, phenylacetylene, etc.) at -78 °C to form pentacoordinated Si, e.g. LiPhSP equilibrates with the starting reagents even at 3:1 ratios of PhLi:SP with no evidence for formation of hexacoordinated species by mass spectral, NMR and quenching studies. Thus, quenching with MeI or Me3SiCl allows isolation of monosubstituted products from RLi:SP; RSi(OR′)3 including some ring-opened oligomers. Comparative studies of reactions of PhLi with Si(OEt)4 allows isolation of mono- and disubstituted products again even at 1:1 ratios of PhLi:Si(OEt)4. However, on standing at -78 °C for long periods of time or on warming to 0 °C, the primary product for both reactions is Ph4Si even with 0.5 equivalents of PhLi. At reaction temperatures ≥0 °C the primary product is again Ph4Si. These results suggest that hexacoordinated intermediates are not part of the substitution mechanism and may suggest that the higher-substituted compounds arise from disproportionation processes. We also briefly describe the conversion of anthracenylSP and 9,9-dimethylfluoreneSP to silsesquioxanes.

Alkyl silane compound (or arylsilanes compd.) manufacturing method (by machine translation)

PROBLEM TO BE SOLVED: alkyl silane compound (or arylsilanes compd.) in order to obtain an effective compd. perfluoroalkylated (or aryl-) is found, novel alkyl silane compound (or aryl compound) and to provide a method of manufacturing. SOLUTION: the following eq. (A-1), (A-2), (A-3), or (A-4) alkylalkoxysilane compd. represented by, alkyl (or aryl demanganese compd.) demanganese compd. reacting and, by perfluoroalkylated (or aryl-), alkyl silane compound (or arylsilanes compd.) can be efficiently manufactured. ( Eq. (A-1), (A-2), (A-3), during and (A-4), R 1 to 1-20 hydrocarbon groups, R 2 silicon atoms and oxygen atoms are each independently selected from the group consisting of at least 1 may also include a kind of carbon number 1-20 hydrocarbon group. ) Selected drawing: no (by machine translation)