2,3,4,5-Tetrafluorobenzoic acid
[CAS 1201-31-6]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluorobenzoic acid series
• Name: 2,3,4,5-Tetrafluorobenzoic acid
• Molecular Formula: C₇H₂F₄O₂
• Molecular Weight: 194.08
• CAS Registry Number: 1201-31-6
• EC Number: 601-673-9
• SMILES: C1=C(C(=C(C(=C1F)F)F)F)C(=O)O

Properties

• Melting point: 85-88 °C

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

2,3,4,5-Tetrafluorobenzoic acid is a fluorinated derivative of benzoic acid, first synthesized through fluorination reactions in the mid-20th century. Researchers sought to introduce fluorine atoms onto the benzene ring to enhance the compound's physicochemical properties, such as solubility, stability, and reactivity. The discovery of 2,3,4,5-tetrafluorobenzoic acid represented a significant advancement in fluorine chemistry, offering a versatile building block for the synthesis of fluorinated organic compounds.

2,3,4,5-Tetrafluorobenzoic acid serves as a valuable building block in organic synthesis, particularly for the preparation of fluorinated compounds. Its fluorinated benzene ring provides a site for further functionalization, allowing chemists to introduce fluorine-containing substituents or incorporate it into more complex molecules.

In the pharmaceutical industry, 2,3,4,5-tetrafluorobenzoic acid is used as an intermediate in the synthesis of fluorinated drugs. Fluorine substitution can modulate the pharmacokinetic and pharmacodynamic properties of drug molecules, enhancing their bioavailability, metabolic stability, and receptor binding affinity.

Fluorinated compounds play a crucial role in the development of agrochemicals, such as pesticides and herbicides. 2,3,4,5-Tetrafluorobenzoic acid can be incorporated into pesticide formulations to enhance their efficacy and environmental safety. Fluorine substitution can increase the compound's resistance to degradation and improve its targeting specificity.

In materials science, fluorinated organic compounds are employed to modify the properties of polymers, surfaces, and coatings. 2,3,4,5-Tetrafluorobenzoic acid can be used as a monomer in the synthesis of fluorinated polymers with desirable characteristics, such as enhanced chemical resistance, thermal stability, and hydrophobicity.

Fluorinated aromatic compounds like 2,3,4,5-tetrafluorobenzoic acid are utilized as fluorescent probes in biological and chemical sensing applications. The presence of fluorine atoms can impart unique spectroscopic properties, such as increased quantum yield and photostability, making them suitable for fluorescence imaging and detection assays. Researchers exploit these properties to label biomolecules, study cellular processes, and develop diagnostic tools for disease detection.

References

2024. Effect of Substituents in the Pentafluorobenzoate and 2,3,4,5- and 2,3,5,6-Tetrafluorobenzoate Anions on the Structure of Cadmium Complexes. Russian Journal of Coordination Chemistry.
DOI: 10.1134/s1070328423601486

2024. Effect of crystallization conditions and position of fluorine substituents on the composition and structure of {CdTb} tetrafluorobenzoate complexes. Russian Chemical Bulletin.
DOI: 10.1007/s11172-024-4142-9

2021. Synthesis and Structure of Bismuth Complexes [(2-MeO)(5-Cl)C6H3]3Bi, [(2-MeO)(5-Cl)C6H3]3Bi[OC(O)CF2Br]2, and [(2-MeO)(5-Br)C6H3]3Bi[OC(O)C6HF4-2,3,4,5]2. Russian Journal of Coordination Chemistry.
DOI: 10.1134/s1070328421070058