3388-04-3

Basic information

• Product Name: Trimethoxy[2-(7-oxabicyclo[4.1.0]hept-3-yl)ethyl]silane
• Synonyms: ((Epoxycyclohexyl)ethyl)trimethoxy silane;(3,4-epoxycyclohexyl)ethyltrimethoxysilane;2-(3,4-Epoxycyclohexyl) ethyltriacetoxysilane;3,4-Epoxycyclohexylethyltrimethoxysilane;3-[2-(Trimethoxysilyl)Ethyl]-7-oxabicyclo[4.1.0]heptane;4-[2-(Trimethoxysilyl)ethyl]-7-oxabicyclo[4.1.0]heptane;A 186;A 186 (Heterocycle)
• CAS NO: 3388-04-3
• Molecular Formula: C₁₁H₂₂O₄Si
• Molecular Weight: 246.38
• EINECS: 222-217-1
• Product Categories: Industrial/Fine Chemicals;Epoxy Silanes (Silane Coupling Agents);Functional Materials;Si (Classes of Silicon Compounds);Silane Coupling Agents;Si-O Compounds;Trialkoxysilanes;silane
• Mol File: 3388-04-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 310 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.065 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0167mmHg at 25°C
• Refractive Index: n20/D 1.451(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: 1.4g/L at 20℃
• BRN: 8980119
• CAS DataBase Reference: Trimethoxy[2-(7-oxabicyclo[4.1.0]hept-3-yl)ethyl]silane(CAS DataBase Reference)
• NIST Chemistry Reference: Trimethoxy[2-(7-oxabicyclo[4.1.0]hept-3-yl)ethyl]silane(3388-04-3)
• EPA Substance Registry System: Trimethoxy[2-(7-oxabicyclo[4.1.0]hept-3-yl)ethyl]silane(3388-04-3)

Safety Data

• Hazard Codes: T
• Statements: 45-46-45/46
• Safety Statements: 53-23-36/37/39-45
• WGK Germany: 3
• RTECS: VV4000000
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 3388-04-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 3388-04-3 differently. You can refer to the following data:
1. Trimethoxy[2-(7-oxabicyclo[4.1.0]hept-3-yl)ethyl]silane may be used as a precursor to form SiCOH film via sol-gel. The silane may be used to functionalize alumina nanoparticles towards the fabrication of polyamide 12/alumina nanocomposites. 4 Basalt fibers were functionalized with this silane and its consequent effect on the fabrication of basalt fiber–epoxidized vegetable oil matrix composite materials was analyzed.Trimethoxy[2-(7-oxabicyclo[4.1.0]hept-3-yl)ethyl]silane can be used as a silane based coupling agent to functionalize a variety of substrates. It modifies the surface to improve the dispersion of nanoparticles. It can be used as an adhesion promoter by treating the precursor material with epoxy silanes.
2. Trimethoxy[2-(7-oxabicyclo[4.1.0]hept-3-yl)ethyl]silane was used as an adhesion promoter during the fabrication of:a photoacid generator activated by two photon excitation. nanoscale polymeric structures (width: 65 nm) using 520 nm femtosecond pulse excitation. Trimethoxy[2-(7-oxabicyclo[4.1.0]hept-3-yl)ethyl]silane may be used as a precursor to form SiCOH film via sol-gel. The silane may be used to functionalize alumina nanoparticles towards the fabrication of polyamide 12/alumina nanocomposites. 4 Basalt fibers were functionalized with this silane and its consequent effect on the fabrication of basalt fiber–epoxidized vegetable oil matrix composite materials was analyzed.

Application

Trimethoxy[2-(7-oxabicyclo[4.1.0]hept-3-yl)ethyl]silane was used as an adhesion promoter during the fabrication of:a photoacid generator activated by two photon excitation.nanoscale polymeric structures (width: 65 nm) using 520 nm femtosecond pulse excitation.

Flammability and Explosibility

Nonflammable

Synthesis

The apparatus of Example B was charged with 148.8 g (1.2 mol) of 1-vinyl-3,4-epoxycyclohexane, 1.3 g of a carboxylic acid promoter, and 0.15 ml of 10% chloroplatinic acid catalyst solution. The flask contents were heated to 89° C. and dropwise addition of 122.8 g {[1.0 mol) of trimethoxysilane was begun. The reaction temperature was controlled at 90°-95° C. with an ice bath. Reaction was maintained at that temperature for half an hour after completion of addition, which took 18 minutes. Analysis by gas chromatography showed a yield of 90% of 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane. This example demonstrates a standard preparation of 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane using commercial chloroplatinic acid.

InChI:InChI=1/C11H22O4Si/c1-12-16(13-2,14-3)7-6-9-4-5-10-11(8-9)15-10/h9-11H,4-8H2,1-3H3

Synthetic route

1,2-Epoxy-4-vinylcyclohexane (106-86-5) + γ-methacryloxypropyltrichlorosilane + trimethoxysilane (2487-90-3) → trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3)

Conditions	Yield
chloroplatinic acid	90%

1,2-Epoxy-4-vinylcyclohexane (106-86-5) + trimethoxysilane (2487-90-3) → trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3)

Conditions	Yield
With 2C4H9O(1-)*Ni(2+)*(x)KCl In tetrahydrofuran at 20℃; for 12h; Glovebox; Inert atmosphere;	74%
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene for 1.66667h; Sealed tube; Heating;
With Pt catalyst In toluene at 80℃; for 1.66667h;

4-(vinyloxy)butan-1-ol (17832-28-9) + trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3) → C26H46O7Si

Conditions	Yield
at 110 - 125℃; under 200 Torr; for 5.5h;	93.9%

triethanolamine (102-71-6) + trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3) → 2-[(3,4-epoxycyclohexyl)ethyl]silatrane

Conditions	Yield
With potassium hydroxide In benzene for 2h; Heating;	90%

bis(2-hydroxyethyl)(2-hydroxybutyl)amine (4435-57-8) + trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3) → 2-[(3,4-epoxycyclohexyl)ethyl]-3-ethylsilatrane

Conditions	Yield
With potassium hydroxide In toluene for 2h; Heating;	88.7%

triisopropanolamine (122-20-3) + trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3) → 2-[(3,4-epoxycyclohexyl)ethyl]-3,7,10-trimethylsilatrane

Conditions	Yield
With potassium hydroxide In toluene for 3h; Heating;	88%

18-crown-6 ether (17455-13-9) + benzene-1,2-diol (120-80-9) + trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3) → potassium [18-crown-6] bis(catecholato)(2-(7-oxabicyclo[4.1.0]heptan-3-yl)ethyl)silicate

Conditions	Yield
With potassium methanolate In methanol at 20℃; for 3h; Inert atmosphere;	85%

carbon dioxide (124-38-9) + trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3) → C12H22O6Si

Conditions	Yield
With C21H12Cl6NO4V; tetrabutylammomium bromide In neat (no solvent) at 85℃; under 7500.75 Torr; for 18h;	85%

carbon dioxide (124-38-9) + trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3) → C12H22O6Si

Conditions	Yield
With tetrabutylammomium bromide In neat (no solvent) at 100℃; for 18h; chemoselective reaction;	77%

3-[N-(3-methoxypropyl)amino]propyltrimethoxysilane + trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3) → 3,3-dimethoxy-7-(3-methoxypropyl)-10-(2-trimethoxysilylethyl)-2-oxa-7-aza-3-sila-bicyclo[6,4,0]dodecane

Conditions	Yield
With zinc(II) chloride In acetonitrile at 80℃; for 3h; Inert atmosphere; High pressure; Autoclave;	70.4%

styrene (292638-84-7) + trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3) → polymer, Mw/Mn = 1.61; monomer(s): styrene; 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane

Conditions	Yield
With bis(cyclopentadienyl)titanium (III) chloride In 1,4-dioxane at 90℃; Kinetics;
With bis(cyclopentadienyl)titanium (III) chloride In 1,4-dioxane at 90℃;

(tris(3-phenylpyrazol-1-yl)hydroborate)Cd(acetate) * toluene + trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3) → hydrotris(3-phenylpyrazol-1-yl)borato(acetato)((2-(3,4-epoxycyclohexyl)ethyl)trimethoxysilane)cadmium(II)

Conditions	Yield
In dichloromethane-d2 not isolated, detected by (113)Cd NMR spectroscopy;

diphenylsilanediol (947-42-2) + trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3) → C53H74O12Si5

Conditions	Yield
With barium hydroxide monohydrate

morpholine (110-91-8) + trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3) → 2-morpholino-4-(2-trimethoxysilylethyl)cyclohexan-1-ol + 2-morpholino-5-(2-trimethoxysilylethyl)cyclohexan-1-ol

Conditions	Yield
With lanthanum(lll) triflate at 110℃; for 2h; Inert atmosphere;

2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate (2494-89-5) + trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3) → C19H33NO10S2Si

Conditions	Yield
With formic acid at 80℃; for 2h; Temperature;

trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3) → C64H104O22Si8(4-)*4Na(1+)

Conditions	Yield
With water; sodium hydroxide In isopropyl alcohol for 8h; Inert atmosphere; Reflux;	0.85 g

C20H37N3O8 + trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane (3388-04-3) → C31H59N3O12Si

Conditions	Yield
at 40 - 50℃; for 2h; Inert atmosphere;

Upstream product

• 106-86-5 1,2-Epoxy-4-vinylcyclohexane 
• 2487-90-3 trimethoxysilane 

Relevant articles and documents

Alkene Hydrosilylation on Oxide-Supported Pt-Ligand Single-Site Catalysts

Heterogeneous single-site catalysts (SSCs), widely regarded as promising next-generation catalysts, blend the easy recovery of traditional heterogeneous catalysts with desired features of homogeneous catalysts: high fraction of active sites and uniform metal centers. We previously reported the synthesis of Pt-ligand SSCs through a novel metal-ligand self-assembly method on MgO, CeO2, and Al2O3 supports (J. Catal. 2018, 365, 303–312). Here, we present their applications in the industrially-relevant alkene hydrosilylation reaction, with 95 % yield achieved under mild conditions. As expected, they exhibit better metal utilization efficiency than traditional heterogeneous Pt catalysts. The comparison with commercial catalysts (Karstedt and Speier) reveals several advantages of these SSCs: higher selectivity, less colloidal Pt formation, less alkene isomerization/hydrogenation, and better tolerance towards functional groups in substrates. Despite some leaching, our catalysts exhibit satisfactory recyclability and the single-site structure remains intact on oxide supports after reaction. Pt single-sites were proved to be the main active sites rather than colloidal Pt formed during the reaction. An induction period is observed in which Pt sites are activated by Cl detachment and replacement by reactant alkenes. The most active species likely involves temporary detachment of Pt from ligand or support. Catalytic performance of Pt SSCs is sensitive to the ligand and support choices, enabling fine tuning of Pt sites. This work highlights the application of heterogeneous SSCs created by the novel metal-ligand self-assembly strategy in an industrially-relevant reaction. It also offers a potential catalyst for future industrial hydrosilylation applications with several improvements over current commercial catalysts.

An Easily Accessed Nickel Nanoparticle Catalyst for Alkene Hydrosilylation with Tertiary Silanes

The first efficient and non-precious nanoparticle catalyst for alkene hydrosilylation with commercially relevant tertiary silanes has been developed. The nickel nanoparticle catalyst was prepared in situ from a simple nickel alkoxide precatalyst Ni(OtBu)2?x KCl. The catalyst exhibits high activity for anti-Markovnikov hydrosilylation of unactivated terminal alkenes and isomerizing hydrosilylation of internal alkenes. The catalyst can be applied to synthesize a single terminal alkyl silane from a mixture of internal and terminal alkene isomers, and to remotely functionalize an internal alkene derived from a fatty acid.

Process for preparing epoxy group-containing silanes

In a process for the preparation of epoxy group-containing alkoxy silanes by hydrosililation of a terminally unsaturated epoxy compound with a hydro-alkoxy silane using a platinum catalyst, the improvement comprising carrying out the hydrosililation in the presence of an alcohol. By this process formation of the internally sililated isomer can be suppressed and the desired terminally sililated poduct can be produced at an approximately 100% selectivity.