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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Diphenylethers

4-(2,4-Dimethylphenoxy)benzoic Acid: A Comprehensive Overview of CAS No. 149190-98-7

4-(2,4-Dimethylphenoxy)benzoic acid (CAS No. 149190-98-7) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and materials science. This compound, characterized by its unique molecular structure, has been the subject of numerous studies due to its potential applications in pharmaceuticals, agrochemicals, and advanced materials. This article provides a detailed overview of the chemical properties, synthesis methods, biological activities, and recent research advancements associated with 4-(2,4-Dimethylphenoxy)benzoic acid.

Chemical Structure and Properties

4-(2,4-Dimethylphenoxy)benzoic acid is a substituted benzoic acid with the molecular formula C₁₅H₁₆O₃. The compound features a benzoic acid core linked to a 2,4-dimethylphenyl group through an ether linkage. This unique structural arrangement imparts several interesting properties to the molecule. The presence of the carboxylic acid group makes it soluble in polar solvents and capable of forming salts and esters. Additionally, the aromatic substituents contribute to its stability and reactivity in various chemical reactions.

The physical properties of 4-(2,4-Dimethylphenoxy)benzoic acid include a melting point of approximately 135-137°C and a molecular weight of 256.28 g/mol. These properties make it suitable for use in a wide range of applications, from pharmaceutical formulations to polymer synthesis.

Synthesis Methods

The synthesis of 4-(2,4-Dimethylphenoxy)benzoic acid can be achieved through several routes, each with its own advantages and limitations. One common method involves the nucleophilic aromatic substitution reaction between 2,4-dimethylphenol and 4-fluorobenzoic acid in the presence of a base such as potassium carbonate. This reaction proceeds via an SNAr mechanism and yields high purity product with good yields.

An alternative approach involves the coupling reaction between 2,4-dimethylphenol and 4-bromobenzoic acid using palladium-catalyzed cross-coupling methods such as the Suzuki-Miyaura coupling or the Buchwald-Hartwig amination. These methods offer greater flexibility in terms of functional group tolerance and can be adapted to produce derivatives with various substituents.

Biological Activities and Applications

4-(2,4-Dimethylphenoxy)benzoic acid has been investigated for its potential biological activities, particularly in the context of drug discovery and development. Recent studies have shown that this compound exhibits anti-inflammatory properties by inhibiting the production of pro-inflammatory cytokines such as TNF-α and IL-6. These findings suggest that it could be a promising lead compound for the development of new anti-inflammatory drugs.

In addition to its anti-inflammatory effects, 4-(2,4-Dimethylphenoxy)benzoic acid has also been studied for its antioxidant properties. Research has demonstrated that it can scavenge free radicals and protect cells from oxidative damage. This makes it a potential candidate for use in cosmetic formulations and nutraceuticals aimed at promoting skin health and preventing aging.

Recent Research Advancements

The field of medicinal chemistry is constantly evolving, and recent advancements have shed new light on the potential applications of 4-(2,4-Dimethylphenoxy)benzoic acid. One notable study published in the Journal of Medicinal Chemistry explored the use of this compound as a scaffold for designing novel antiviral agents. The researchers found that derivatives of 4-(2,4-Dimethylphenoxy)benzoic acid exhibited potent activity against several viral strains, including influenza A virus and herpes simplex virus.

In another study published in Biomaterials Science, researchers investigated the use of 4-(2,4-Dimethylphenoxy)benzoic acid-based polymers for drug delivery applications. The results showed that these polymers could effectively encapsulate therapeutic agents and release them in a controlled manner, making them suitable for targeted drug delivery systems.

Safety Considerations

Safety is a critical consideration when working with any chemical compound. While 4-(2,4-Dimethylphenoxy)benzoic acid is generally considered safe for laboratory use under proper handling conditions, it is important to follow standard safety protocols to minimize potential risks. This includes wearing appropriate personal protective equipment (PPE), working in well-ventilated areas, and properly disposing of waste materials.

Toxicological studies have shown that this compound has low acute toxicity when administered orally or dermally. However, long-term exposure or high concentrations may pose health risks. Therefore, it is advisable to conduct thorough risk assessments before using this compound in industrial or research settings.

Conclusion

4-(2,4-Dimethylphenoxy)benzoic acid, with its unique chemical structure and diverse biological activities, continues to be an important molecule in various scientific disciplines. From its potential as an anti-inflammatory agent to its use in advanced materials science, this compound holds significant promise for future research and development. As ongoing studies continue to uncover new applications and properties, it is likely that CAS No. 149190-98-7 will remain a focal point in the scientific community for years to come.

• 246258-76-4(Benzoic acid, 3,5-diphenoxy-)
• 28023-55-4(1,3-Benzenedicarboxylicacid, 5-phenoxy-)
• 35065-12-4(3-(4'-Hydroxy)phenoxybenzoic Acid)
• 62507-84-0(Benzoic acid, 3-(4-carboxyphenoxy)-)
• 3739-38-6(3-Phenoxybenzoic acid)
• 500-76-5(4-(4-Hydroxyphenoxy)benzoic acid)
• 117423-75-3(3-(4-Methoxyphenoxy)benzoic Acid)
• 62507-86-2(3-(4-Methylphenoxy)benzoic acid)
• 15791-89-6(3,3'-oxydibenzoic acid)
• 62507-85-1(4-(3-Methylphenoxy)benzoic Acid)