2,4,6,8-Tetravinyl-2,4,6,8-tetramethylcyclotetrasiloxane
[CAS# 2554-06-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Siloxane
• Name: 2,4,6,8-Tetravinyl-2,4,6,8-tetramethylcyclotetrasiloxane
• Synonyms: 2,4,6,8-Tetramethyl-2,4,6,8-tetravinylcyclotetrasiloxane
• Molecular Formula: C₁₂H₂₄O₄Si₄
• Molecular Weight: 344.66
• CAS Registry Number: 2554-06-5
• EC Number: 219-863-1
• SMILES: C[Si]1(O[Si](O[Si](O[Si](O1)(C)C=C)(C)C=C)(C)C=C)C=C

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*, 0.997 g/mL (Expl.)
• Melting point: -44 °C (Expl.)
• Index of Refraction: 1.455, Calc.^*, 1.434 (Expl.)
• Boiling Point: 247.8±23.0 °C (760 mmHg), Calc.^*, 110 °C (10 mmHg) (Expl.)
• Flash Point: 94.3±23.0 °C, Calc.^*, 112 °C (Expl.)

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H319
• Safety Statements: P264+P265-P280-P305+P351+P338-P337+P317

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Reproductive toxicity	Repr.	1B	H360
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

2,4,6,8-Tetravinyl-2,4,6,8-tetramethylcyclotetrasiloxane is an important organosilicon compound that belongs to the family of cyclotetrasiloxanes. This substance is characterized by a cyclotetrasiloxane ring structure, where four silicon atoms are bonded to both vinyl groups and methyl groups. The presence of the vinyl groups provides this compound with the potential for polymerization, making it highly useful in various industrial applications. The tetramethyl groups, on the other hand, contribute to its chemical stability and enhance its overall hydrophobic characteristics.

The discovery of 2,4,6,8-Tetravinyl-2,4,6,8-tetramethylcyclotetrasiloxane emerged as part of ongoing research into improving the versatility of silicon-based compounds. Its molecular structure allows it to be utilized in the synthesis of various siloxane-based polymers and materials. The ability to polymerize through its vinyl groups makes it an attractive candidate for use in the production of elastomers and coatings, where strong, flexible, and durable materials are required.

The synthesis of 2,4,6,8-Tetravinyl-2,4,6,8-tetramethylcyclotetrasiloxane typically involves the reaction of tetramethylcyclotetrasiloxane with a vinyl-containing reagent under controlled conditions. The synthesis process ensures that the vinyl groups are evenly distributed around the cyclotetrasiloxane ring, maintaining the stability of the structure while making it suitable for further polymerization. This compound can also be synthesized using various catalysts and solvents that promote the addition of vinyl groups to the silicon ring, which is a crucial step for polymer formation.

One of the key applications of 2,4,6,8-Tetravinyl-2,4,6,8-tetramethylcyclotetrasiloxane is in the production of high-performance silicone elastomers. These elastomers are valued for their excellent thermal stability, flexibility, and resistance to aging. By incorporating 2,4,6,8-Tetravinyl-2,4,6,8-tetramethylcyclotetrasiloxane into the polymerization process, manufacturers are able to create materials that exhibit superior mechanical properties, making them suitable for a wide range of industrial applications, including seals, gaskets, and insulation.

The compound is also used in the formulation of coatings and adhesives, where its ability to crosslink through the vinyl groups enhances the durability and adhesion properties of the final product. Coatings made from siloxane polymers that include 2,4,6,8-Tetravinyl-2,4,6,8-tetramethylcyclotetrasiloxane offer excellent water repellency, resistance to environmental degradation, and the ability to maintain their integrity in harsh conditions. This makes them ideal for applications in the automotive, aerospace, and construction industries, where performance under extreme conditions is essential.

In addition, 2,4,6,8-Tetravinyl-2,4,6,8-tetramethylcyclotetrasiloxane is used in the synthesis of advanced silicone resins. These resins are employed in the production of high-temperature-resistant coatings, electrical insulation materials, and other products requiring enhanced thermal and mechanical properties. The compound's ability to undergo controlled polymerization reactions is key to tailoring the properties of the resulting resins to meet the specific requirements of these applications.

The versatility of 2,4,6,8-Tetravinyl-2,4,6,8-tetramethylcyclotetrasiloxane makes it a valuable component in the synthesis of custom silicone-based materials with a wide array of properties. Its applications in elastomers, coatings, adhesives, and resins have positioned it as an essential material in industries that rely on high-performance, durable, and chemically stable materials.

References

2023. Superhydrophobization of cotton textiles by difunctional cyclic siloxanes via thiol-ene click reaction. Cellulose, 30(7).
DOI: 10.1007/s10570-023-05204-w

2021. Robust fluorinated siloxane copolymers via initiated chemical vapor deposition for corrosion protection. Journal of Materials Science, 56(12).
DOI: 10.1007/s10853-021-06060-4

2020. Synthetic Methods and Applications of Functional and Reactive Silicone Polymers. Reactive and Functional Polymers Volume One.
DOI: 10.1007/978-3-030-43403-8_13