1,1,5,5-Tetramethyl-3,3-diphenyltrisiloxane
[CAS# 17875-55-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Siloxane
• Name: 1,1,5,5-Tetramethyl-3,3-diphenyltrisiloxane
• Synonyms: Bis(dimethylsiloxy)diphenylsilane; Tetramethyl diphenyl dihydrogen trisiloxane
• Molecular Formula: C₁₆H₂₄O₂Si₃
• Molecular Weight: 332.62
• CAS Registry Number: 17875-55-7
• EC Number: 241-828-4
• SMILES: C[Si](C)O[Si](C1=CC=CC=C1)(C2=CC=CC=C2)O[Si](C)C

Properties

• Density: 0.9936 g/mL
• Refractive index: 1.5330
• Boiling Point: 292.1±13.0 °C (760 mmHg), Calc.^*
• Flash Point: 130.5±19.8 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Danger
• Risk Statements: H302-H361-H372-H410
• Safety Statements: P273-P201-P264-P280-P301+P330+P331-P312

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

1,1,5,5-Tetramethyl-3,3-diphenyltrisiloxane is an organosilicon compound that plays an important role in various industrial applications due to its unique molecular structure and properties. As a member of the trisiloxane family, this compound consists of a silicon-oxygen backbone with both methyl and phenyl groups attached to the silicon atoms. The presence of both methyl and phenyl groups on the trisiloxane structure provides a balance of flexibility and rigidity, making it suitable for a wide range of applications in materials science, especially in the formulation of silicones and other polymeric systems.

The discovery of 1,1,5,5-Tetramethyl-3,3-diphenyltrisiloxane is tied to the ongoing development of new siloxane compounds in the mid-20th century. Researchers sought to improve the properties of conventional silicones by introducing different functional groups that would enhance their thermal stability, chemical resistance, and mechanical properties. The introduction of phenyl groups into the siloxane structure was of particular interest, as it provided increased thermal stability and improved resistance to oxidation and other environmental stresses. This led to the synthesis of 1,1,5,5-Tetramethyl-3,3-diphenyltrisiloxane as a compound with enhanced properties suitable for use in demanding applications.

The synthesis of 1,1,5,5-Tetramethyl-3,3-diphenyltrisiloxane typically involves the reaction of trimethylsilane and diphenylsilane in the presence of a catalyst under controlled conditions. This method allows for the selective attachment of the methyl and phenyl groups to the trisiloxane backbone, creating a highly stable compound with excellent properties for use in industrial and commercial products. The reaction conditions can be tailored to control the degree of substitution, ensuring that the final product possesses the desired characteristics in terms of stability, viscosity, and reactivity.

One of the primary applications of 1,1,5,5-Tetramethyl-3,3-diphenyltrisiloxane is in the formulation of silicone fluids and oils. These materials are used in a variety of industries, including automotive, electronics, and cosmetics, due to their excellent lubrication properties, high thermal stability, and resistance to oxidation. The compound's unique structure, with both methyl and phenyl groups, allows it to act as a stable intermediate in the production of silicones that are used in lubricants, greases, and insulating oils for electrical equipment. The phenyl groups contribute to the overall stability of the material at higher temperatures, while the methyl groups provide flexibility and low surface tension, making the compound useful in a range of lubrication applications.

In addition to its role in silicone fluids, 1,1,5,5-Tetramethyl-3,3-diphenyltrisiloxane is widely used as an intermediate in the production of more complex siloxane-based compounds. It serves as a building block for the synthesis of silicone rubbers and elastomers, which are used in a wide range of applications, including automotive seals, gaskets, medical devices, and consumer goods. The compound's ability to form cross-linked structures and its resistance to environmental factors such as moisture, heat, and UV radiation make it an ideal component in the formulation of these high-performance materials.

Another important application of 1,1,5,5-Tetramethyl-3,3-diphenyltrisiloxane is in the electronics industry, where it is used in the manufacture of thermal management materials and electronic encapsulants. The compound's excellent thermal stability and insulating properties make it an ideal choice for use in the protection of sensitive electronic components. In particular, it is used in the development of heat-resistant coatings and insulating materials that prevent overheating and protect electronic devices from damage caused by excessive heat.

Furthermore, 1,1,5,5-Tetramethyl-3,3-diphenyltrisiloxane is employed in surface modification processes. It is used as a component in hydrophobic coatings, providing enhanced water-repellent properties to surfaces such as glass, metals, and textiles. These coatings are useful in a variety of industries, including construction, automotive, and textiles, where water resistance is essential.

In conclusion, 1,1,5,5-Tetramethyl-3,3-diphenyltrisiloxane is a highly versatile and valuable compound in the field of materials science. Its unique combination of methyl and phenyl groups provides it with exceptional thermal stability, flexibility, and resistance to environmental degradation, making it an essential ingredient in the production of silicone fluids, rubbers, electronic materials, and surface coatings.

References

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