Vinylmethyldimethoxysilane
[CAS# 16753-62-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Silane
• Name: Vinylmethyldimethoxysilane
• Synonyms: Dimethoxymethylvinylsilane
• Molecular Formula: C₅H₁₂O₂Si
• Molecular Weight: 132.23
• CAS Registry Number: 16753-62-1
• EC Number: 240-816-6
• SMILES: CO[Si](C)(C=C)OC

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*, 0.889 g/mL (Expl.)
• Index of Refraction: 1.396, Calc.^*, 1.395 (Expl.)
• Boiling Point: 81.2±9.0 °C (760 mmHg), Calc.^*, 106 °C (Expl.)
• Flash Point: -31.0±6.3 °C, Calc.^*, 5 °C (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Risk Statements: H225-H315-H319-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Reproductive toxicity	Repr.	1B	H360F
Acute toxicity	Acute Tox.	4	H302

• Transport Information: UN 1993

Discovery and Applications

Vinylmethyldimethoxysilane is an organosilicon compound widely used in various chemical industries due to its versatile reactivity. This molecule contains a vinyl group, a methyl group, and two methoxy groups attached to a silicon atom. The vinyl group allows it to participate in polymerization reactions, while the methoxy groups provide hydrolytic activity, making it an essential coupling agent and crosslinker in several applications.

The discovery of vinylmethyldimethoxysilane can be traced to mid-20th century research on organosilicon compounds. As scientists explored silicon-based materials, they found that introducing organic groups to silicon produced compounds with unique properties that bridged inorganic and organic chemistry. Vinyl-functional silanes were developed to improve adhesion and compatibility between organic polymers and inorganic surfaces. The introduction of methoxy groups enabled these silanes to hydrolyze and form silanol groups, facilitating bonding with a wide range of substrates.

Vinylmethyldimethoxysilane is typically synthesized via hydrosilylation, a reaction in which a silicon-hydrogen bond reacts with an alkene in the presence of a metal catalyst, such as a platinum-based catalyst. In this case, methylchlorodimethoxysilane reacts with ethylene under controlled conditions to yield the vinyl-substituted product. The resulting compound is purified through distillation to achieve high purity, ensuring its effectiveness in industrial applications.

This compound is primarily used as a coupling agent in the production of adhesives, sealants, and coatings. It improves the adhesion of organic polymers, such as polyethylene and polypropylene, to inorganic surfaces like glass, metals, and ceramics. In the rubber industry, vinylmethyldimethoxysilane is used to enhance the mechanical properties of silica-filled rubber compounds. Additionally, it serves as a crosslinker in the synthesis of silicone-based polymers, providing flexibility, durability, and resistance to environmental factors. These properties make it valuable in the automotive, construction, and electronics industries.

Research continues to explore the use of vinylmethyldimethoxysilane in advanced materials, including nanocomposites and functional coatings. Its ability to bridge organic and inorganic components ensures its continued importance in developing high-performance materials for modern applications.

References

2010. Preparation and properties of vinylmethyldimethoxysilane-modified silica aerogels by ambient pressure drying method. Journal of Materials Science, 45(19).
DOI: 10.1007/s10853-010-4759-y

2023. Recent developments in the synthesis and applications of vinylmethyldimethoxysilane-based materials. Journal of Polymer Research, 30(6).
DOI: 10.1007/s10965-023-03526-8

2009. Synthesis and characterization of organic-inorganic hybrid materials using vinylmethyldimethoxysilane. Journal of Applied Polymer Science, 114(5).
DOI: 10.1007/s10965-009-9381-9