(3,3,3-Trifluoropropyl)dichloromethylsilane
[CAS# 675-62-7]

Identification

• Classification: Chemical reagent >> Silane reagent
• Name: (3,3,3-Trifluoropropyl)dichloromethylsilane
• Synonyms: dichloro-methyl-(3,3,3-trifluoropropyl)silane
• Molecular Formula: C₄H₇Cl₂F₃Si
• Molecular Weight: 211.09
• CAS Registry Number: 675-62-7
• EC Number: 211-623-4
• SMILES: C[Si](CCC(F)(F)F)(Cl)Cl

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*, 1.261 g/mL (Expl.)
• Index of Refraction: 1.382, Calc.^*, 1.385 (Expl.)
• Boiling Point: 113.8±35.0 °C (760 mmHg), Calc.^*, 121-122 °C (Expl.)
• Flash Point: 22.6±25.9 °C, Calc.^*, 15 °C (Expl.)

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

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Risk Statements: H225-H314-H332
• Safety Statements: P210-P260-P303+P361+P353-P305+P351+P338-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1A	H314
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Flammable liquids	Flam. Liq.	3	H226
Serious eye damage	Eye Dam.	1	H318
Flammable liquids	Flam. Liq.	2	H225
Skin corrosion	Skin Corr.	1B	H314
Substances or mixtures corrosive to metals	Met. Corr.	1	H290

Discovery and Applications

(3,3,3-Trifluoropropyl)dichloromethylsilane is an organosilicon compound with the chemical formula C₆H₈Cl₂F₃Si. This chemical belongs to the class of silanes, which are compounds containing silicon atoms bonded to organic groups and chlorine atoms. It is specifically characterized by the presence of a trifluoropropyl group (CF₃CH₂CH₂–) and two chlorine atoms bonded to a silicon atom, alongside a methyl group (-CH₃) in its structure.

The compound is typically synthesized through a reaction involving the appropriate trifluoropropyl alcohol or trifluoropropyl iodide and a chlorosilane. Such reactions often take place under anhydrous conditions and may involve catalysts to facilitate the formation of the organosilicon bond. The exact synthetic pathway may vary depending on the desired purity and yield of the product, but the essential process involves introducing the trifluoropropyl group into the silicon-chlorine framework.

(3,3,3-Trifluoropropyl)dichloromethylsilane is an important intermediate in the chemical industry due to its unique properties. The trifluoropropyl group imparts characteristics such as high chemical stability and resistance to temperature extremes, making it highly suitable for use in applications that demand high-performance materials. The chlorine atoms in the structure also provide functionality for further reactions, enabling the compound to be used in the synthesis of more complex silane derivatives and other specialty chemicals.

One of the primary applications of (3,3,3-trifluoropropyl)dichloromethylsilane is in the formulation of surface treatments and coatings. It can be used to modify the surface properties of materials like metals, glass, and ceramics, improving characteristics such as water repellency, chemical resistance, and adhesion. By incorporating this compound into coatings, it is possible to create protective layers that exhibit both hydrophobicity and resistance to corrosion, making them suitable for use in industries such as electronics, automotive, and construction.

In the electronics industry, (3,3,3-trifluoropropyl)dichloromethylsilane is used in the development of advanced materials for semiconductor devices. Its ability to modify surfaces and enhance the performance of electronic components makes it an important precursor in the creation of materials that are durable and capable of withstanding harsh environmental conditions. The fluorinated nature of the trifluoropropyl group also contributes to the compound's ability to form stable bonds with other materials, facilitating the creation of integrated circuits and other complex electronic components.

Additionally, (3,3,3-trifluoropropyl)dichloromethylsilane is employed in the formulation of specialty adhesives and sealants. The incorporation of the trifluoropropyl group imparts low surface energy to these products, which can improve their ability to bond to non-polar surfaces, such as fluoropolymers or other fluorinated materials. This property is particularly valuable in industries where the use of high-performance adhesives is required, including aerospace, automotive, and manufacturing.

Furthermore, the compound is used in the production of hydrophobic and oleophobic materials. The presence of the trifluoropropyl group is known to enhance the water- and oil-repellent properties of surfaces, which is beneficial for creating coatings for textiles, packaging materials, and medical devices that need to resist contamination from water or oils.

While (3,3,3-trifluoropropyl)dichloromethylsilane has many beneficial applications, safety precautions must be observed during its handling. As a chlorosilane derivative, it can be reactive, especially with water, which could lead to the release of hydrogen chloride gas. Appropriate storage and handling procedures should be followed to minimize exposure, particularly in environments where moisture control is critical.

In summary, (3,3,3-trifluoropropyl)dichloromethylsilane is a versatile organosilicon compound with applications in the electronics, coatings, and adhesives industries. Its ability to modify surfaces, along with its chemical stability and hydrophobicity, makes it valuable for producing high-performance materials. Through its role in these applications, the compound contributes to the development of advanced products with enhanced durability and resistance to environmental stressors.

References

2022. Amidation of α-Amino Acids Using Dichloro(methyl)(3,3,3-trifluoropropyl)silane and Imidazole without Conventional Protection and Deprotection of α-Amino Group. Synlett, 33(14).
DOI: 10.1055/a-1865-1792

2009. Studies and developments of Lebedev institute of synthetic rubber in the field of new fluoroelastomers. Russian Journal of Applied Chemistry, 82(12).
DOI: 10.1134/s1070427209120295