2,2,2-Trifluoroethyl methacrylate
[CAS# 352-87-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Acid ester compound
• Name: 2,2,2-Trifluoroethyl methacrylate
• Synonyms: 1,1-Dihydroperfluoroethyl methacrylate; 2-Methyl-2-propenoic acid 2,2,2-trifluoroethyl ester
• Molecular Formula: C₆H₇F₃O₂
• Molecular Weight: 168.11
• CAS Registry Number: 352-87-4
• EC Number: 206-525-3
• SMILES: CC(=C)C(=O)OCC(F)(F)F

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*, 1.181 g/mL (Expl.)
• Index of Refraction: 1.363, Calc.^*, 1.361 (Expl.)
• Boiling Point: 115.5 °C (760 mmHg), Calc.^*, 123.9 °C (Expl.)
• Flash Point: 16.7 °C, Calc.^*, 16 °C (Expl.)

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

Safety Data

• Hazard Symbols: GHS02;GHS06;GHS07 Danger
• Risk Statements: H225-H301-H315-H319-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P270-P271-P280-P301+P316-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P330-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
Acute toxicity	Acute Tox.	3	H301
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	3	H331
Skin sensitization	Skin Sens.	1	H317
Flammable liquids	Flam. Liq.	3	H226

• Transport Information: UN 3272

Discovery and Applications

2,2,2-Trifluoroethyl methacrylate (CF₃CH₂O₂CCH(CH₃)=CH₂) is a fluorinated methacrylate ester that contains a trifluoroethyl (-CF₃CH₂O-) functional group. It is a colorless to slightly yellow liquid with characteristic reactivity typical of methacrylate esters, particularly in radical polymerization reactions. The trifluoroethyl moiety enhances its physicochemical properties, including low surface energy, hydrophobicity, and chemical resistance, making it useful in various industrial and scientific applications.

The compound is widely used in the synthesis of fluorinated polymers and copolymers. Its incorporation into polymer matrices imparts desirable properties such as water and oil repellency, low refractive index, and improved thermal and chemical stability. These characteristics have led to its application in coatings, adhesives, and specialty resins where fluorinated functionalities provide enhanced durability and performance.

In surface modification technologies, 2,2,2-trifluoroethyl methacrylate has been utilized to develop water- and stain-resistant materials. When polymerized, the resulting fluorinated films exhibit reduced adhesion to contaminants and improved weathering resistance. These properties are valuable in protective coatings for optical devices, electronics, and aerospace applications. Additionally, copolymers incorporating this monomer are used in biomedical and microfluidic applications due to their ability to control surface energy and interaction with biological environments.

The reactivity of 2,2,2-trifluoroethyl methacrylate allows for copolymerization with a range of monomers, including other acrylates, methacrylates, and vinyl-based compounds. This versatility enables the design of tailored polymer structures with specific mechanical, thermal, and surface properties.

Handling of 2,2,2-trifluoroethyl methacrylate requires appropriate precautions due to its potential volatility and reactivity. As with other methacrylate esters, storage in a cool, dry environment is recommended to prevent premature polymerization. The presence of inhibitors may be necessary to ensure stability during storage and transport.

The established applications of 2,2,2-trifluoroethyl methacrylate in polymer chemistry and material science demonstrate its significance in advancing fluoropolymer technology. Its unique combination of fluorinated and methacrylate functionalities continues to support its role in the development of high-performance materials.

References

2024. Dip-Coating Method of Preparation of a Silicon-Modified Acrylic Resin Hydrophobic Coating with Corrosion Resistance for Copper-Aluminum Composite. Journal of Materials Engineering and Performance, 33(24).
DOI: 10.1007/s11665-024-10414-9

2024. Superhydrophobic melamine sponge prepared by radiation-induced grafting technology for efficient oil-water separation. Nuclear Science and Techniques, 35(9).
DOI: 10.1007/s41365-024-01507-0

2024. Investigation of the effect of fluorine and silane-containing monomers on waterborne hybrid (alkyd/styrene acrylic) latexes. Journal of Coatings Technology and Research, 21(3).
DOI: 10.1007/s11998-023-00873-5