1,3,5-Tris[(3,3,3-trifluoropropyl)methyl]cyclotrisiloxane
[CAS# 2374-14-3]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Cyclic hydrocarbon
• Name: 1,3,5-Tris[(3,3,3-trifluoropropyl)methyl]cyclotrisiloxane
• Synonyms: 1,3,5-Trimethyl-1,3,5-tris(3,3,3-trifluoropropyl)cyclotrisiloxane
• Molecular Formula: C₁₂H₂₁F₉O₃Si₃
• Molecular Weight: 468.54
• CAS Registry Number: 2374-14-3
• EC Number: 219-154-7
• SMILES: C[Si]1(O[Si](O[Si](O1)(C)CCC(F)(F)F)(C)CCC(F)(F)F)CCC(F)(F)F

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*, 1.24 g/mL (Expl.)
• Melting point: 34-36 °C (Expl.)
• Index of Refraction: 1.381, Calc.^*, 1.382 (Expl.)
• Boiling Point: 253.5±35.0 °C (760 mmHg), Calc.^*, 135 °C (22 mmHg) (Expl.)
• Flash Point: 107.1±25.9 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H315-H319-H361-H372-H373
• Safety Statements: P203-P260-P264-P264+P265-P270-P280-P302+P352-P305+P351+P338-P318-P319-P321-P332+P317-P337+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	2	H361
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

1,3,5-Tris[(3,3,3-trifluoropropyl)methyl]cyclotrisiloxane, also known as tris(trifluoropropyl)methylcyclotrisiloxane, is a specialized organosilicon compound that has gained attention for its unique properties and applications, particularly in materials science and chemical industries. This compound consists of a cyclotrisiloxane ring with three trifluoropropylmethyl groups attached to the silicon atoms. These groups confer distinct characteristics to the compound, including low surface energy, high thermal stability, and chemical resistance.

The discovery of 1,3,5-Tris[(3,3,3-trifluoropropyl)methyl]cyclotrisiloxane is part of the broader effort to develop advanced fluorosilicone compounds that combine the beneficial properties of silicon and fluorine. The fluorine atoms in the molecule provide exceptional resistance to oils, greases, and other contaminants, making these compounds ideal for high-performance applications. Cyclotrisiloxane derivatives, in particular, have been the subject of much research due to their ability to form stable, three-dimensional structures that enhance the mechanical properties of materials while maintaining flexibility and durability.

The synthesis of 1,3,5-Tris[(3,3,3-trifluoropropyl)methyl]cyclotrisiloxane typically involves a controlled reaction between a fluorinated silane precursor and a suitable catalyst. The process allows for the selective attachment of trifluoropropyl groups to the cyclotrisiloxane ring, ensuring the formation of a stable compound. This synthesis is often carried out under mild conditions to prevent the decomposition of the sensitive fluorine groups, which could compromise the integrity of the final product.

One of the primary applications of 1,3,5-Tris[(3,3,3-trifluoropropyl)methyl]cyclotrisiloxane is in the formulation of high-performance coatings and sealants. The compound's low surface energy and hydrophobic nature make it highly effective in creating protective barriers on surfaces exposed to harsh environmental conditions. It is commonly used in coatings for electronics, automotive parts, and other industrial materials where moisture, dirt, and chemicals must be repelled. The trifluoropropyl groups enhance the compound's ability to resist staining, weathering, and corrosion, which significantly extends the lifespan of the coated materials.

In addition to its role in coatings, 1,3,5-Tris[(3,3,3-trifluoropropyl)methyl]cyclotrisiloxane is also utilized in lubrication and sealing applications. The compound's chemical stability and ability to withstand extreme temperatures and pressures make it ideal for use in specialized lubricants and sealants for mechanical systems. These include applications in the aerospace, automotive, and manufacturing industries, where high levels of performance are required under challenging conditions. Its resistance to chemical degradation and high thermal stability ensure the longevity and effectiveness of lubricants and seals.

Another important application is in the field of electronics, where 1,3,5-Tris[(3,3,3-trifluoropropyl)methyl]cyclotrisiloxane is used as an insulating material for sensitive electronic components. The compound's dielectric properties, coupled with its resistance to moisture and electrical conductivity, make it an excellent choice for applications in which electrical insulation is critical. This includes the encapsulation of microelectronic devices, ensuring the protection of internal circuits from environmental damage.

Beyond these applications, the compound has also been explored for use in other areas such as personal care products and surfactants. Its ability to reduce surface tension makes it a promising ingredient in formulations designed to modify the surface properties of various substrates. In personal care, it could potentially be used in formulations for hair care products, providing smoothness and resistance to moisture while maintaining the flexibility and integrity of hair fibers.

The versatility and unique properties of 1,3,5-Tris[(3,3,3-trifluoropropyl)methyl]cyclotrisiloxane have positioned it as an important compound in both industrial and consumer product applications. Its ability to combine the benefits of fluorine and silicone, such as chemical resistance, thermal stability, and low surface energy, makes it a valuable material in advanced coatings, lubricants, and insulation technologies.

References

2019. Volatile Methyl Siloxanes in Polar Regions. Volatile Methylsiloxanes in the Environment.
DOI: 10.1007/698_2019_388

2013. Polymethyl(hexafluoroalkyl)siloxane Rubbers: Preparation and thermal properties. Russian Journal of Applied Chemistry, 86(4).
DOI: 10.1134/s1070427213040319

2008. Synthesis of poly[methyl(3,3,3-trifluoropropyl)siloxane]-b-poly(ethylene oxide) block copolymers. Journal of Zhejiang University-SCIENCE A, 9(9).
DOI: 10.1631/jzus.a0820162