3-(3-Trifluoromethylphenyl)propionic acid
[CAS# 585-50-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic acid
• Name: 3-(3-Trifluoromethylphenyl)propionic acid
• Synonyms: m-(Trifluoromethyl)hydrocinnamic acid
• Molecular Formula: C₁₀H₉F₃O₂
• Molecular Weight: 218.17
• CAS Registry Number: 585-50-2
• EC Number: 639-439-3
• SMILES: C1=CC(=CC(=C1)C(F)(F)F)CCC(=O)O

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Melting point: 34-37 °C (Expl.)
• Index of Refraction: 1.475, Calc.^*
• Boiling Point: 268.7±35.0 °C (760 mmHg), Calc.^*
• Flash Point: 116.3±25.9 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

3-(3-Trifluoromethylphenyl)propionic acid is an organic compound belonging to the family of aromatic carboxylic acids. It features a trifluoromethyl group attached to the 3-position of the phenyl ring, with a propionic acid chain connected at the para-position. The trifluoromethyl substituent imparts unique electronic properties to the molecule, significantly influencing its reactivity and potential biological activity. This compound is valued for its role in the pharmaceutical and agrochemical industries as well as in materials science.

The discovery of 3-(3-trifluoromethylphenyl)propionic acid can be traced back to studies on fluorinated aromatic compounds in the mid-20th century. Researchers were particularly interested in introducing fluorine atoms into organic frameworks to improve chemical stability, modify lipophilicity, and enhance bioavailability. The trifluoromethyl group was recognized as a key functional group for these purposes due to its strong electron-withdrawing characteristics and resistance to metabolic degradation. These properties were explored in the synthesis of propionic acid derivatives, leading to the development of 3-(3-trifluoromethylphenyl)propionic acid.

This compound has gained attention in pharmaceutical research as a precursor or intermediate in the synthesis of nonsteroidal anti-inflammatory drugs (NSAIDs) and other therapeutic agents. The trifluoromethyl group enhances the bioactivity of the molecules by improving their interaction with target enzymes and receptors. Derivatives of 3-(3-trifluoromethylphenyl)propionic acid have shown potential in the treatment of inflammatory diseases and other conditions requiring targeted enzyme inhibition.

In the agrochemical sector, 3-(3-trifluoromethylphenyl)propionic acid serves as a scaffold for the development of herbicides and fungicides. Its ability to penetrate biological membranes and interact with enzymatic pathways makes it an effective starting point for designing compounds that regulate plant growth or protect crops from fungal infections. The trifluoromethyl group further contributes to environmental stability, ensuring prolonged activity in field conditions.

The compound also finds application in materials science, particularly in the design of fluorinated polymers and coatings. The unique electronic properties of the trifluoromethyl group allow for modifications that enhance hydrophobicity, thermal stability, and chemical resistance. These attributes are particularly valuable in the development of high-performance materials for industrial and consumer applications.

3-(3-Trifluoromethylphenyl)propionic acid continues to be a focus of research, with efforts directed toward optimizing its synthetic routes and exploring its applications in new fields. Its multifunctional nature and versatile chemical profile make it an important compound for advancing both theoretical studies and practical innovations.

References

2016. Syntheses of Cinacalcet: An Enantiopure Active Pharmaceutical Ingredient (API). Synthesis.
DOI: 10.1055/s-0035-1561506

2015. Boron-Catalyzed N-Alkylation of Amines Using Carboxylic Acids. Synfacts.
DOI: 10.1055/s-0035-1560694