18042-54-1

Basic information

• Product Name: PHENYLTRIACETOXYSILANE
• Synonyms: phenyl-silanetriotriacetate;PHENYLTRIACETOXYSILANE;Phenyltriacetoxysilane(Triacetoxy(phenyl)silane;TRIACETOXY(PHENYL)SILANE;Phenylsilanetriol triacetate;Monophenyltriacetoxysilane;PHENYLTRIACETOXYSILANE, tech-90;Phenylsilanetriyl triacetate
• CAS NO: 18042-54-1
• Molecular Formula: C₁₂H₁₄O₆Si
• Molecular Weight: 282.32
• EINECS: 241-952-9
• Product Categories: Acetoxy Silanes;Crosslinkers;Crosslinking Agents
• Mol File: 18042-54-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 34.5 °C
• Boiling Point: 158 °C
• Flash Point: 102°C
• Appearance: Colorless or yellowish transparent liquid
• Density: 1.194
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.495
• CAS DataBase Reference: PHENYLTRIACETOXYSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLTRIACETOXYSILANE(18042-54-1)
• EPA Substance Registry System: PHENYLTRIACETOXYSILANE(18042-54-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• TSCA: Yes
• Hazardous Substances Data: 18042-54-1(Hazardous Substances Data)

Usage

Description

Phenyltriacetoxysilane is a clear to yellowish liquid with an acrid odor of acetic acid (vinegar). It is a silane compound that hydrolyzes in the presence of moisture, releasing acetic acid and forming silanols. These silanols can react with themselves to produce siloxanes or bind to inorganic substrates, making it a versatile chemical intermediate.

Uses

Used in Adhesive Industry:
Phenyltriacetoxysilane is used as a coupling agent for enhancing the adhesion between organic and inorganic materials. Its ability to form siloxanes and bind to inorganic substrates improves the durability and strength of adhesive bonds.
Used in Coatings Industry:
Phenyltriacetoxysilane is used as a surface modifier to improve the adhesion, corrosion resistance, and weatherability of coatings. Its reactivity with inorganic substrates allows for better integration of the coating with the underlying material, resulting in a more robust and long-lasting finish.
Used in Electronics Industry:
Phenyltriacetoxysilane is used as a component in the fabrication of electronic devices, such as semiconductors and solar cells. Its ability to form siloxanes and bind to inorganic substrates contributes to the creation of stable and efficient electronic components.
Used in Construction Industry:
Phenyltriacetoxysilane is used as a sealant and waterproofing agent in construction applications. Its reactivity with inorganic substrates allows for the formation of a durable and water-resistant barrier, protecting structures from moisture and other environmental factors.
Used in Textile Industry:
Phenyltriacetoxysilane is used as a finishing agent in the textile industry to improve the durability, water resistance, and stain resistance of fabrics. Its ability to bind to inorganic substrates enhances the performance and longevity of textile products.

InChI:InChI=1/C12H14O6Si/c1-9(13)16-19(17-10(2)14,18-11(3)15)12-7-5-4-6-8-12/h4-8H,1-3H3

Upstream product

• 108-24-7 acetic anhydride 
• 98-13-5 Phenyltrichlorosilane 
• 563-63-3 silver(I) acetate 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 591-87-7 Allyl acetate 
• 694-53-1 phenylsilane 
• 2996-92-1 phenyl trimethylsiloxane 
• 123-62-6 propionic acid anhydride 
• 2754-27-0 trimethylsilyl acetate 

Downstream Products

• 14661-99-5 4,4'-diphenyl-[2⁴,2'⁴]bi[3,5,8-trioxa-1-aza-4-sila-2,6,7(1,2)-tribenzena-bicyclo[2.2.2]octaphanyl] 
• 18758-83-3 3-(dimethyl-phenyl-silanyloxy)-1,1,5,5-tetramethyl-1,3,5-triphenyl-trisiloxane 
• 14661-98-4 4-phenyl-3,5,8-trioxa-1-aza-4-sila-2,6,7(1,2)-tribenzena-bicyclo[2.2.2]octaphane 
• 17875-58-0 acetoxy-di-tert-butoxy-phenyl-silane 
• 18537-00-3 1,3,5-triphenyl-1,1,3,5,5-pentahydroxytrisiloxane 

Relevant articles and documents

Carbonyl and ester C-O bond hydrosilylation using κ4-diimine nickel catalysts

The synthesis of alkylphosphine-substituted α-diimine (DI) ligands and their subsequent addition to Ni(COD)2 allowed for the preparation of (iPr2PPrDI)Ni and (tBu2PPrDI)Ni. The solid state structures of both compounds were found to feature a distorted tetrahedral geometry that is largely consistent with the reported structure of the diphenylphosphine-substituted variant, (Ph2PPr DI)Ni. To explore and optimize the synthetic utility of this catalyst class, all three compounds were screened for benzaldehyde hydrosilylation activity at 1.0 mol% loading over 3 h at 25 °C. Notably, (Ph2PPr DI)Ni was found to be the most efficient catalyst while phenyl silane was the most effective reductant. A broad scope of aldehydes and ketones were then hydrosilylated, and the silyl ether products were hydrolyzed to afford alcohols in good yield. When attempts were made to explore ester reduction, inefficient dihydrosilylation was noted for ethyl acetate and no reaction was observed for several additional substrates. However, when an equimolar solution of allyl acetate and phenyl silane was added to 1.0 mol% (Ph2PPr DI)Ni, complete ester C-O bond hydrosilylation was observed within 30 min at 25 °C to generate propylene and PhSi(OAc)3. The scope of this reaction was expanded to include six additional allyl esters, and under neat conditions, turnover frequencies of up to 990 h-1 were achieved. This activity is believed to be the highest reported for transition metal-catalyzed ester C-O bond hydrosilylation. Proposed mechanisms for (Ph2PPr DI)Ni-mediated carbonyl and allyl ester C-O bond hydrosilylation are also discussed.

Unusual transformations of the PhSiFCl group

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