2,3,4-Trifluorobenzoic acid
[CAS# 61079-72-9]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluorobenzoic acid series
• Name: 2,3,4-Trifluorobenzoic acid
• Molecular Formula: C₇H₃F₃O₂
• Molecular Weight: 176.09
• CAS Registry Number: 61079-72-9
• EC Number: 612-077-3
• SMILES: C1=CC(=C(C(=C1C(=O)O)F)F)F

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting point: 140-142 °C (Expl.)
• Index of Refraction: 1.491, Calc.^*
• Boiling Point: 245.3±35.0 °C (760 mmHg), Calc.^*
• Flash Point: 102.1±25.9 °C, Calc.^*

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

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
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2,3,4-Trifluorobenzoic acid is a fluorinated aromatic carboxylic acid with the molecular formula C(_7)H(_3)F(_3)O(_2). It consists of a benzene ring substituted with three fluorine atoms at the 2-, 3-, and 4-positions and a carboxylic acid group. This compound is notable for its high electronegativity, which imparts distinct chemical and physical properties, making it valuable in various fields of chemistry and materials science.

The synthesis and study of trifluorobenzoic acids, including 2,3,4-trifluorobenzoic acid, became prominent in the mid-20th century as interest in fluorine-containing compounds grew. Fluorinated compounds were recognized for their unique reactivity, stability, and biological activity, leading to their extensive exploration. The compound can be synthesized through multi-step methods, such as selective electrophilic fluorination or direct fluorination of precursor aromatic systems. Advances in synthetic fluorine chemistry have enabled more efficient production of such compounds.

In organic synthesis, 2,3,4-trifluorobenzoic acid is a valuable intermediate. Its trifluorinated aromatic ring enhances the electrophilic nature of the compound, facilitating reactions like nucleophilic aromatic substitution (SNAr). This makes it useful in the preparation of complex fluorinated compounds, which are essential in the pharmaceutical, agrochemical, and material industries.

The trifluorinated structure of this acid contributes to its application in drug discovery and design. Fluorination is known to improve metabolic stability, membrane permeability, and bioavailability of compounds, making 2,3,4-trifluorobenzoic acid a precursor in synthesizing biologically active molecules. Many fluorinated derivatives derived from it have shown potential in medicinal chemistry for developing anti-inflammatory, antiviral, and anticancer agents.

Additionally, 2,3,4-trifluorobenzoic acid has applications in materials science. The presence of fluorine atoms enhances thermal and chemical stability, making derivatives of this acid suitable for high-performance polymers, liquid crystal materials, and specialty coatings.

Despite its versatility, the use of 2,3,4-trifluorobenzoic acid requires careful handling due to the potential environmental and health concerns associated with fluorinated chemicals. Research is ongoing to develop sustainable synthesis methods and to assess the environmental impact of fluorinated compounds.

The compound's trifluorinated nature has solidified its role in modern chemistry, with continued advancements in its applications demonstrating its significant potential across multiple domains.

References

2024. Alternative Synthesis of Cobimetinib. Pharmaceutical Chemistry Journal, 58(1).
DOI: 10.1007/s11094-024-03130-0

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

2009. Experimental and calculation aspects of vibrational spectra and optimized geometry of 2,3,4-tri-fluoro-benzoic acid dimer. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 74(5).
DOI: 10.1016/j.saa.2009.09.017