1067-53-4

Basic information

• Product Name: Vinyl tris(2-methoxyethoxy) silane
• Synonyms: gf58;NUCA 172;prosil248;q174;sh6030;Silane, tris(2-methoxyethoxy)vinyl-;Silicone A-172;siliconea-172
• CAS NO: 1067-53-4
• Molecular Formula: C₁₁H₂₄O₆Si
• Molecular Weight: 280.39
• EINECS: 213-934-0
• Product Categories: Vinyl;Functional Materials;Si (Classes of Silicon Compounds);Silane Coupling Agents;Si-O Compounds;Trialkoxysilanes;Vinyl Silanes (Silane Coupling Agents);Vinylsilanes, Allylsilanes;Adhesion Promoters;Coupling Agents;Surface Modifiers;silane
• Mol File: 1067-53-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: -30 °C
• Boiling Point: 136.2 °C5.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /Liquid
• Density: 1.034 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00381mmHg at 25°C
• Refractive Index: n20/D 1.43(lit.)
• Storage Temp.: -196°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10[at 20 ℃]
• Water Solubility: REACTS
• Sensitive: Moisture Sensitive
• BRN: 1795316
• CAS DataBase Reference: Vinyl tris(2-methoxyethoxy) silane(CAS DataBase Reference)
• NIST Chemistry Reference: Vinyl tris(2-methoxyethoxy) silane(1067-53-4)
• EPA Substance Registry System: Vinyl tris(2-methoxyethoxy) silane(1067-53-4)

Safety Data

• Hazard Codes: Xn,T
• Statements: 21-36-62-61-20/21/22
• Safety Statements: 26-36/37-53-45-36/37/39
• RIDADR: UN 1993
• WGK Germany: 1
• RTECS: VV6826000
• TSCA: Yes
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 1067-53-4(Hazardous Substances Data)

Usage

Description

Vinyltris(2-methoxyethoxy)silane is a vinyl-functional coupling agent that promotes adhesion among unsaturated, polyester-type resins or crosslinked polyethylene resins or elastomers and inorganic substrates, including fiber glass, silica, silicates and many metal oxides. When used as coupling agent, it reduces the sensitivity of the products’ mechanical and electrical properties to heat and/or moisture. Vinyl tris(2-methoxyethoxy) silane is mainly applied in these aspects: As an efficient adhesion promoter for various mineral-filled polymers, improving mechanical and electrical properties especially after exposure to moisture. A co-monomer for the preparation of different polymers such as polyethylene or acrylics. Those polymers show an improved adhesion to inorganic surfaces and they can also be crosslinked with moisture. Improving the compatibility of fillers with polymers, leading to a better dispersibility, reduced melt viscosity and easier processing of filled plastics. Pre-treating of glass, metals, or ceramic surfaces, improve the adhesion of coatings on these surfaces and corrosion resistance.

Chemical Properties

Colorless transparent liquid

Flammability and Explosibility

Notclassified

InChI:InChI=1/C11H24O6Si/c1-5-18(15-9-6-12-2,16-10-7-13-3)17-11-8-14-4/h5H,1,6-11H2,2-4H3

Synthetic route

(vinyl)trimethoxylsilane (2768-02-7) + 2-methoxy-ethanol (109-86-4) → tris(2-methoxy ethoxy)-vinyl silane (1067-53-4)

Conditions	Yield
With potassium aluminum sulfate at 70 - 80℃; for 2h; Reagent/catalyst;	99.5%

2-methoxy-ethanol (109-86-4) + trichlorovinylsilane (75-94-5) → tris(2-methoxy ethoxy)-vinyl silane (1067-53-4)

Conditions	Yield
byproducts: HCl; addn. of a small excess of CH3OCH2CH2OH to boiling (CH2CH)SiCl3; boiling til formation of HCl stops;;	46%

2-methoxy-ethanol (109-86-4) + Triethoxyvinylsilane (78-08-0) → tris(2-methoxy ethoxy)-vinyl silane (1067-53-4) + di(ethoxy)(2-methoxyethoxy)(vinyl)silane + ethoxydi[2-methoxyethoxy](vinyl)silane

Conditions	Yield
With CBV 780 at 110℃; for 0.0833333h; Microwave irradiation;

tris(2-methoxy ethoxy)-vinyl silane (1067-53-4) + para-iodoanisole (696-62-8) → 4-Methoxystyrene (637-69-4)

Conditions	Yield
With sodium hydroxide; 4-hydroxyacetophenone oxime-derived palladacycle In water for 3h; Hiyama reaction; Heating;	79%

tris(2-methoxy ethoxy)-vinyl silane (1067-53-4) + 1-Iodonaphthalene (90-14-2) → 1-vinylnaphthalene (826-74-4)

Conditions	Yield
With sodium hydroxide; 4-hydroxyacetophenone oxime-derived palladacycle In water at 120℃; for 0.166667h; Hiyama reaction; microwave irradiation;	73%

tris(2-methoxy ethoxy)-vinyl silane (1067-53-4) + para-bromoacetophenone (99-90-1) → 1-(4-vinylphenyl)ethanone (10537-63-0)

Conditions	Yield
With sodium hydroxide; palladium diacetate In water at 120℃; for 0.166667h; microwave irradiation;	70%

tris(2-methoxy ethoxy)-vinyl silane (1067-53-4) + N,N'-bis(1-ethylpropyl)-3,4:9,10-perylenebis(dicarboximide) (110590-81-3) → N,N'-bis(3-pentyl)-2,5,8,11-tetrakis{2-[tri(2-methoxyethoxy)silyl]ethyl}perylene-3,4:9,10-tetracarboxylic acid bisimide (1361061-50-8)

Conditions	Yield
With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In 1,3,5-trimethyl-benzene at 160℃; for 60h; Inert atmosphere;	64%

Triethoxysilane (998-30-1) + tris(2-methoxy ethoxy)-vinyl silane (1067-53-4) → C17H40O9Si2

Conditions	Yield
With ruthenium(III) 2,4-pentanedionate at 120℃; for 6h;	54%

tris(2-methoxy ethoxy)-vinyl silane (1067-53-4) + N,N'-bis[2-(2-methoxyethoxy)ethyl]perylene-3,4:9,10-tetracarboxylic acid bisimide (1361061-51-9) → N,N'-bis[2-(2-methoxyethoxy)ethyl]-2,5,8,11-tetrakis{2-[tris(2-methoxyethoxy)silyl]ethyl}perylene-3,4:9,10-tetracarboxylic acid bisimide (1361061-52-0)

Conditions	Yield
With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In 1,3,5-trimethyl-benzene at 160℃; for 48h; Inert atmosphere;	7%

tungsten hexacarbonyl (14040-11-0) + tris(2-methoxy ethoxy)-vinyl silane (1067-53-4) → [W(CO)5(η2-tris(2-methoxyethyloxy)vinylsilane)] (870299-13-1) + trans-[W(CO)4(η2-tris(2-methoxyethyloxy)vinylsilane)2] (870299-14-2)

Conditions	Yield
In n-heptane byproducts: CO; Irradiation (UV/VIS); under N2 atm. using Schlenk techniques; soln. of W(CO)6 and vinylsilane in n-heptane irradiated at room temp. using 200 W high pressure Hg lamp for 1-3 h; solvent removed (vac., room temp.); monitored by NMR and IR spectroscopy; sepn. was possible by slow fractional sublimation in vac. at 20-60°C;

Upstream product

• 109-86-4 2-methoxy-ethanol 
• 75-94-5 trichlorovinylsilane 
• 2768-02-7 (vinyl)trimethoxylsilane 
• 78-08-0 Triethoxyvinylsilane 

Downstream Products

• 10537-63-0 1-(4-vinylphenyl)ethanone 
• 637-69-4 4-Methoxystyrene 
• 826-74-4 1-vinylnaphthalene 

Relevant articles and documents

Ester exchange method for preparing vinyl tri-(2- methoxy ethyoxyl)-silane

The invention relates to an ester exchange method for preparing vinyl tri-(2- methoxy ethyoxyl)-silane, and belongs to the technical field of organic chemical. The ester exchange method uses ethylene glycol monomethyl ether and vinyl trimethoxy silane as raw materials, uses neutral double salt type catalyst to perform the ester exchange reaction, and generates tri-(2- methoxy ethyoxyl)-silane. Through filtering and recycling, the catalyst can be repeatedly used. Compared with traditional esterification method, the method has the advantages that 1, the ester exchange reaction process cannot cause the deepened color of product, methanol is removed by distilling after reaction, and the product can be obtained by direct filtering. 2. The catalyst can be recycled and repeatedly used for 10 times, and the activity is still kept.

Process for preparing low-chloride or chloride-free alkoxysilanes

A process for preparing an alkoxysilane with an acidic chloride content of less than 10 ppm by weight, comprising: reacting a chlorosilane with an alcohol in a water-free and solvent-free phase to form a product mixture containing alkoxysilane and residual acidic chloride, with removal of resultant hydrogen chloride from the product mixture, then adding liquid or gaseous ammonia, in an amount corresponding to a stoichiometric excess, based on the content of acidic chloride, to form an ammonia-containing product mixture, treating the ammonia-containing product mixture at a temperature between 10 and 50 DEG C., wherein the ammonia and acidic chloride undergo neutralization, to form a crude product, and optionally, then separating off a salt formed in the course of neutralization, from the crude product, and recovering the alkoxysilane by distilling the crude product.