376353-50-3

Basic information

• Product Name: 3,4-METHYLENEDIOXYPHENYLTRIETHOXYSILANE
• Synonyms: 3,4-METHYLENEDIOXYPHENYLTRIETHOXYSILANE;1-(Triethoxysilyl)-3,4-Methylenedioxybenzene;1,3-Benzodioxol-5-Yl(Triethoxy)Silane
• CAS NO: 376353-50-3
• Molecular Formula: C₁₃H₂₀O₅Si
• Molecular Weight: 284.38
• Mol File: 376353-50-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 298.7°C at 760 mmHg
• Flash Point: 107.5°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 0.00222mmHg at 25°C
• Refractive Index: 1.503
• CAS DataBase Reference: 3,4-METHYLENEDIOXYPHENYLTRIETHOXYSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-METHYLENEDIOXYPHENYLTRIETHOXYSILANE(376353-50-3)
• EPA Substance Registry System: 3,4-METHYLENEDIOXYPHENYLTRIETHOXYSILANE(376353-50-3)

Safety Data

• TSCA: No
• Hazardous Substances Data: 376353-50-3(Hazardous Substances Data)

Usage

General Description

3,4-METHYLENEDIOXYPHENYLTRIETHOXYSILANE is a chemical compound with the molecular formula C16H22O4Si. It is a silane coupling agent that is used as a surface modifier and adhesion promoter for organic and inorganic materials such as glass, metal, and plastics. It contains a phenyl group with methylenedioxy linkages and three ethoxy groups attached to a silicon atom. 3,4-METHYLENEDIOXYPHENYLTRIETHOXYSILANE is used in various industrial applications, including the production of sealants, coatings, and adhesives, where it improves the adhesion properties of the materials to which it is applied. Additionally, it can also be used as a crosslinking agent in the synthesis of organic-inorganic hybrid materials.

InChI:InChI=1/C13H20O5Si/c1-4-16-19(17-5-2,18-6-3)11-7-8-12-13(9-11)15-10-14-12/h7-9H,4-6,10H2,1-3H3

Upstream product

• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 78-10-4 tetraethoxy orthosilicate 
• 998-30-1 Triethoxysilane 
• 1228306-22-6 benzo[d][1,3]dioxol-5-yl-diazonium tosylate 

Downstream Products

• 4421-09-4 piperonylonitrile 
• 134952-85-5 2-methoxy-5-(3',4'-methylenedioxyphenyl)cyclohepta-2,4,6-trien-1-one 

Relevant articles and documents

Application of palladium-catalyzed allylic arylation to the synthesis of a (±)-7-deoxypancratistatin analogue

(Chemical Equation Presented) Palladium-catalyzed coupling of an aryl siloxane and an allylic carbonate proceeded in good yield to give an adduct that was converted to an analogue of (±)-7-deoxypancratistatin.

The Hiyama Cross-Coupling Reaction at Parts Per Million Levels of Pd: In Situ Formation of Highly Active Spirosilicates in Glycol Solvents

A palladium NNC-pincer complex at a 5 mol ppm loading efficiently catalyzed the Hiyama coupling reaction of aryl bromides with aryl(trialkoxy)silanes in propylene glycol to give the corresponding biaryls in excellent yields. This method was applied to the syntheses of adapalene and a biaryl-type liquid-crystalline compound, as well as to the derivatization of dextromethorphan and norfloxacin. ESI-MS and NMR analyses of the reaction mixture suggested the formation of pentacoordinate spirosilicate intermediates in situ. Preliminary theoretical studies revealed that the glycol-derived silicate intermediates formed in situ are quite reactive silicon reagents in the transmetalation step.

A facile and efficient synthesis of aryltriethoxysilanes via sonochemical Barbier-type reaction

A series of aryltriethoxysilanes was synthesized from the reaction mixture of aryl bromide, Mg powder, 1,2-dibromoethane and tetraethyl orthosilicate in THF under ultrasound. This sonochemical Barbier-type reaction provides a simple and efficient method for preparation of aryltriethoxysilanes. The Hiyama cross-coupling reaction of phenyltriethoxysilane with bromobenzene was investigated under different palladium catalysts and Pd(PhCN)2Cl2 was found to be the best choice.