Sodium 4-trifluoromethylbenzoate
[CAS# 25832-58-0]

Identification

• Name: Sodium 4-trifluoromethylbenzoate
• Synonyms: 4-Trifluoromethylbenzoic acid sodium salt; Sodium 4-(trifluoromethyl)benzoate
• Molecular Formula: C₈H₄F₃NaO₂
• Molecular Weight: 212.10
• CAS Registry Number: 25832-58-0
• EC Number: 921-850-7
• SMILES: C1=CC(=CC=C1C(=O)[O-])C(F)(F)F.[Na+]

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

Sodium 4-trifluoromethylbenzoate was discovered through organic synthesis research aimed at developing novel chemical compounds with unique properties. It was first synthesized by reacting 4-trifluoromethylbenzoic acid with sodium hydroxide, resulting in the formation of the sodium salt of 4-trifluoromethylbenzoic acid. This discovery marked a significant milestone in the field of fluorine chemistry, offering chemists a new compound with diverse applications.

Sodium 4-trifluoromethylbenzoate serves as a valuable intermediate in the synthesis of pharmaceutical compounds. Its trifluoromethyl group imparts desirable properties to drug candidates, including enhanced metabolic stability and improved pharmacokinetics. Chemists utilize this compound in the development of various drugs, such as antivirals, anti-inflammatory agents, and anticancer medications.

In the agricultural sector, Sodium 4-trifluoromethylbenzoate finds application as a key ingredient in the formulation of agrochemicals and pesticides. Its fluorinated benzene structure enhances the efficacy of pesticide formulations by improving their systemic absorption and biological activity against pests and pathogens. Agricultural scientists incorporate this compound into pesticide formulations to protect crops from damage caused by insects, fungi, and weeds.

Sodium 4-trifluoromethylbenzoate is utilized as a catalyst in organic synthesis reactions. Its trifluoromethyl group serves as a useful directing group in transition metal-catalyzed C–H activation reactions, enabling the selective functionalization of aromatic compounds. Organic chemists employ this compound to facilitate the synthesis of complex molecules with diverse structures and functionalities.

In organic chemistry laboratories, Sodium 4-trifluoromethylbenzoate is used as a solvent and reagent in various synthetic transformations. Its solubility in common organic solvents and compatibility with a wide range of functional groups make it a versatile reagent for organic synthesis. Chemists utilize this compound in reactions such as esterification, amidation, and nucleophilic substitution to introduce trifluoromethyl-containing moieties into target molecules.

Sodium 4-trifluoromethylbenzoate is employed in material science applications for the synthesis of functional materials with tailored properties. Its fluorinated benzene structure allows for the modification of material surfaces, enhancing properties such as hydrophobicity, chemical resistance, and adhesion. Researchers utilize this compound in the fabrication of coatings, films, and polymers for various industrial and technological applications.

References

1990. Fluorinated anthracyclines: Synthesis and biological activity. Investigational New Drugs.
DOI: 10.1007/bf00216918