3-(Trifluoromethyl)benzoic acid
[CAS# 454-92-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic acid
• Name: 3-(Trifluoromethyl)benzoic acid
• Synonyms: 3-Carboxybenzotrifluoride; m-Trifluoromethylbenzoic acid; alpha,alpha,alpha-Trifluoro-m-toluic acid
• Molecular Formula: C₈H₅F₃O₂
• Molecular Weight: 190.12
• CAS Registry Number: 454-92-2
• EC Number: 207-230-2
• SMILES: C1=CC(=CC(=C1)C(F)(F)F)C(=O)O

Properties

• Melting point: 104-106 °C
• Boiling point: 238.4 °C (775 mmHg)

Safety Data

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

Hazard Classification

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

Discovery and Applications

3-(Trifluoromethyl)benzoic acid, a compound of significant chemical interest, was discovered through synthetic organic chemistry methodologies. Scientists meticulously crafted this molecule by introducing a trifluoromethyl group onto the benzene ring of benzoic acid. This innovative synthesis opened avenues for exploring its diverse applications across various scientific domains.

This compound serves as a valuable building block in pharmaceutical synthesis. Its trifluoromethyl group enhances drug potency and metabolic stability. Medicinal chemists utilize it to design new drug candidates with improved pharmacological properties, targeting diseases such as cancer, inflammation, and microbial infections.

3-(Trifluoromethyl)benzoic acid finds applications in agrochemical formulations. Its presence enhances the efficacy and persistence of herbicides and pesticides, contributing to crop protection and agricultural productivity.

In material science, this compound acts as a precursor for synthesizing fluorinated polymers and functional materials. These materials exhibit unique properties such as chemical resistance, thermal stability, and surface modification capabilities, making them suitable for coatings, membranes, and electronic devices.

As a source of fluorine, 3-(Trifluoromethyl)benzoic acid facilitates the synthesis of various fluorinated organic molecules. These compounds have widespread applications in medicinal chemistry, materials science, and chemical synthesis due to the unique physicochemical properties imparted by fluorine substitution.

Chemists use this compound as a versatile tool for exploring new reaction methodologies and catalyst design. Its trifluoromethyl group influences reaction pathways and selectivity, enabling the synthesis of complex molecules efficiently.

Fluorine-18 labeled derivatives of 3-(Trifluoromethyl)benzoic acid serve as valuable tracers in positron emission tomography (PET) imaging. These radiotracers enable non-invasive visualization of biological processes in vivo, aiding in disease diagnosis and drug development.

References

2023. Pesticides and TPs from SLU, Sweden.
DOI: 10.5281/zenodo.4687924

2016. Rapid ion-exchange matrix removal for a decrease of detection limits in the analysis of salt-rich reservoir waters for fluorobenzoic acids by liquid chromatography coupled with tandem mass spectrometry. Analytical and Bioanalytical Chemistry, 409(4).
DOI: 10.1007/s00216-016-0060-5

2021. Palladium-Catalyzed ortho-C-H Functionalization of Aromatic Ketones for Site-Selective Fluorination. Synfacts, 17(6).
DOI: 10.1055/s-0040-1720644