2-(Trifluoromethyl)acrylic acid
[CAS# 381-98-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Halogenated aliphatic hydrocarbon
• Name: 2-(Trifluoromethyl)acrylic acid
• Synonyms: 2-(Trifluoromethyl)propenoic acid
• Molecular Formula: C₄H₃F₃O₂
• Molecular Weight: 140.06
• CAS Registry Number: 381-98-6
• EC Number: 627-408-7
• SMILES: C=C(C(=O)O)C(F)(F)F

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 51-52 ºC (Expl.)
• Index of Refraction: 1.36, Calc.^*
• Boiling Point: 192.6±40.0 ºC (760 mmHg), Calc.^*, 190.9 ºC (Expl.)
• Flash Point: 81.7 ºC, Calc.^*, 82 ºC (Expl.)

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

Safety Data

• Hazard Symbols: GHS06 Danger
• Hazard Statements: H314
• Precautionary Statements: P260-P264-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin corrosion	Skin Corr.	1C	H314
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318

• Transport Information: UN 3261

Discovory and Applicatios

2-(Trifluoromethyl)acrylic acid (C₅HF₃O₂) is a fluorinated organic compound that contains both an acrylic acid group and a trifluoromethyl group. The trifluoromethyl group (–CF₃) is known for its unique electronic properties, which significantly alter the chemical reactivity and stability of the compound. This makes 2-(trifluoromethyl)acrylic acid a valuable building block in organic synthesis, with a wide range of applications in chemical research, materials science, and the development of specialty chemicals.

The compound was first synthesized and studied as part of a broader effort to develop fluorinated analogs of common organic compounds. The trifluoromethyl group, due to its electron-withdrawing nature, affects the reactivity of the acrylic acid structure by increasing the electrophilicity of the double bond in the acrylic acid moiety. This reactivity enhancement has made it a valuable intermediate in the synthesis of a variety of fluorinated organic compounds.

2-(Trifluoromethyl)acrylic acid is primarily used as a precursor in the synthesis of fluorinated derivatives that have applications in the pharmaceutical, agrochemical, and polymer industries. The presence of the trifluoromethyl group enhances the hydrophobicity and metabolic stability of these derivatives, which is beneficial for designing drugs and agrochemicals with improved bioavailability and longer-lasting effects.

In the pharmaceutical industry, 2-(trifluoromethyl)acrylic acid is used in the synthesis of various fluorinated compounds that exhibit enhanced biological activity. The incorporation of fluorine atoms into organic molecules can increase their metabolic stability, reduce the rate of degradation, and improve their ability to interact with biological targets. This makes fluorinated compounds attractive candidates for the development of new therapeutics, particularly in the field of oncology, anti-inflammatory drugs, and antibiotics. By modifying the structure of the molecule with a trifluoromethyl group, researchers can fine-tune the physicochemical properties of the compound to optimize its activity and selectivity.

In agrochemicals, 2-(trifluoromethyl)acrylic acid is used in the synthesis of herbicides, fungicides, and insecticides. The trifluoromethyl group imparts high stability and enhances the potency of agrochemical products, which is crucial for improving their effectiveness in protecting crops from pests and diseases. Fluorinated agrochemicals are known for their resistance to degradation in the environment, which increases their longevity and efficacy in agricultural applications.

The compound is also of interest in the development of fluorinated polymers. The incorporation of trifluoromethyl groups into polymer chains can enhance the chemical resistance, thermal stability, and mechanical properties of the resulting materials. 2-(Trifluoromethyl)acrylic acid can be polymerized to form fluorinated polymers that are used in high-performance coatings, adhesives, and sealants. These polymers are particularly useful in industries that require materials with excellent resistance to solvents, high temperatures, and aggressive chemicals.

Furthermore, 2-(trifluoromethyl)acrylic acid can be employed in the synthesis of advanced materials for electronics and optoelectronics. The fluorine atoms can impart unique electronic properties to materials, making them useful for applications in organic semiconductors, organic light-emitting diodes (OLEDs), and other electronic devices. The incorporation of fluorinated groups into the molecular structure can also enhance the stability and performance of these devices, particularly under harsh operating conditions.

The environmental impact of fluorinated compounds, including 2-(trifluoromethyl)acrylic acid, is an area of ongoing concern. While these compounds offer many benefits in terms of chemical stability and performance, they are also known for their persistence in the environment. Fluorinated chemicals can accumulate and potentially pose risks to ecosystems. As a result, the production, use, and disposal of such compounds must be carefully managed to minimize their environmental footprint.

In conclusion, 2-(trifluoromethyl)acrylic acid is a versatile and valuable fluorinated organic compound with a wide range of applications in pharmaceuticals, agrochemicals, polymer synthesis, and materials science. Its unique combination of the trifluoromethyl group and acrylic acid structure makes it an important building block for the development of fluorinated compounds with enhanced properties. However, due to the environmental persistence of fluorinated chemicals, their use must be carefully regulated to mitigate potential ecological risks.

References

2024. Fluorinated PAMAM-Arginine Carrier Prodrugs for pH-Sensitive Sustained Ibuprofen Delivery. Pharmaceutical Research, 41(8).
DOI: 10.1007/s11095-024-03747-6

2023. Smart soils track the formation of pH gradients across the rhizosphere. Plant and Soil, 494(1-2).
DOI: 10.1007/s11104-023-06151-y

2022. Preparation and application of tebuconazole molecularly imprinted polymer for detection of pesticide residues in tobacco leaves. Journal of Polymer Research, 29(5).
DOI: 10.1007/s10965-022-03036-z