2,2,2-Trifluoroethyl acrylate
[CAS# 407-47-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Acid ester compound
• Name: 2,2,2-Trifluoroethyl acrylate
• Synonyms: TFEA
• Molecular Formula: C₅H₅F₃O₂
• Molecular Weight: 154.09
• CAS Registry Number: 407-47-6
• EC Number: 206-987-6
• SMILES: C=CC(=O)OCC(F)(F)F

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*, 1.216 g/mL (Expl.)
• Index of Refraction: 1.351, Calc.^*, 1.35 (Expl.)
• Boiling Point: 98.7±35.0 °C (760 mmHg), Calc.^*, 46 °C (125 mmHg) (Expl.)
• Flash Point: 12.2±0.0 °C, Calc.^*, 12 °C (Expl.)

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

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Risk Statements: H225-H302-H312-H315-H319-H332-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P317-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
Skin irritation	Skin Irrit.	2	H315
Flammable liquids	Flam. Liq.	2	H225
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Flammable liquids	Flam. Liq.	3	H226
Eye irritation	Eye Irrit.	2A	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

• Transport Information: UN 3272

Discovery and Applications

2,2,2-Trifluoroethyl acrylate is an important fluorinated monomer known for its role in the synthesis of specialty polymers and coatings. It consists of an acrylate group attached to a trifluoroethyl moiety, combining the reactivity of the acrylate double bond with the unique properties of fluorinated groups. This compound offers enhanced thermal stability, chemical resistance, and low surface energy, making it suitable for advanced material applications.

The discovery of 2,2,2-trifluoroethyl acrylate is part of the broader exploration of fluorinated acrylates in the mid-20th century. Chemists sought to develop monomers that could impart desirable properties such as hydrophobicity and chemical resistance to polymers. Early studies on fluoroalkyl acrylates demonstrated that introducing fluorine atoms into acrylate structures significantly altered the resulting polymers' performance characteristics. These discoveries laid the foundation for the commercial use of fluorinated acrylates in various industries.

The synthesis of 2,2,2-trifluoroethyl acrylate typically involves the esterification of acrylic acid with 2,2,2-trifluoroethanol. This reaction is carried out under acidic conditions, often using sulfuric acid or other acid catalysts. The process yields high purity trifluoroethyl acrylate, which can be further purified through distillation. Alternative methods include transesterification, where methyl acrylate reacts with 2,2,2-trifluoroethanol in the presence of a catalyst.

2,2,2-Trifluoroethyl acrylate is used extensively in the production of fluorinated polymers and copolymers. These polymers are valued for their water and oil repellency, chemical resistance, and durability. Applications include protective coatings, adhesives, and surface treatments for textiles and paper products. In the electronics industry, polymers derived from 2,2,2-trifluoroethyl acrylate are used to manufacture insulating materials and components that require low dielectric constants. The compound is also used in the development of high-performance resins and sealants for automotive and aerospace applications.

Ongoing research focuses on expanding the applications of 2,2,2-trifluoroethyl acrylate in nanomaterials, functional coatings, and biomedical devices. Its unique combination of reactivity and fluorinated properties ensures its continued importance in the development of advanced materials.

References

2023. Recent advances in fluorinated polymers: synthesis and diverse applications. Science China Chemistry, 66(11).
DOI: 10.1007/s11426-023-1831-8

2016. Applications in the Syntheses of Natural Products and Drug Molecules. Science of Synthesis.
URL: SD-222-00159

2013. N-Heterocyclic Carbene Catalyzed Transesterification of Polytrifluoroethyl Acrylates. Synlett, 24(10).
DOI: 10.1055/s-0033-1338950