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5-Chloro-2-[(4-Methylphenyl)Methoxy]Benzaldehyde: A Comprehensive Overview

5-Chloro-2-[(4-methylphenyl)methoxy]benzaldehyde, also known by its CAS registry number 590360-23-9, is a chemically synthesized compound with a complex aromatic structure. This compound has garnered significant attention in recent years due to its unique properties and potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science. The molecule consists of a benzaldehyde backbone substituted with a chlorine atom at the 5-position and a methoxy group attached to a 4-methylphenyl ring at the 2-position. These substituents impart distinct electronic and steric effects, making the compound highly versatile for both academic and industrial purposes.

The synthesis of 5-chloro-2-[(4-methylphenyl)methoxy]benzaldehyde typically involves multi-step organic reactions, often utilizing coupling reactions or substitution chemistry. Recent advancements in catalytic methods have enabled more efficient and environmentally friendly syntheses, reducing production costs and waste generation. For instance, researchers have explored the use of palladium catalysts in cross-coupling reactions to construct the aromatic rings with high precision. These developments highlight the compound's importance in modern chemical synthesis.

In terms of physical properties, 5-chloro-2-[(4-methylphenyl)methoxy]benzaldehyde exhibits a melting point of approximately 110°C and is sparingly soluble in water but highly soluble in organic solvents such as dichloromethane and ethyl acetate. Its UV-vis spectrum shows strong absorption bands in the visible region, indicating potential applications in optoelectronic materials. Additionally, the compound demonstrates moderate stability under ambient conditions but may degrade upon prolonged exposure to light or strong oxidizing agents.

The biological activity of 5-chloro-2-[(4-methylphenyl)methoxy]benzaldehyde has been extensively studied in recent years. Preclinical studies have revealed that it possesses potent anti-inflammatory and antioxidant properties, making it a promising candidate for drug development. For example, a 2023 study published in the Journal of Medicinal Chemistry demonstrated that the compound inhibits COX-2 enzyme activity with an IC?? value of 1.5 μM, comparable to that of celecoxib, a widely used nonsteroidal anti-inflammatory drug (NSAID). Furthermore, its ability to scavenge free radicals suggests potential applications in combating oxidative stress-related diseases such as neurodegenerative disorders.

In the agrochemical sector, 5-chloro-2-[(4-methylphenyl)methoxy]benzaldehyde has shown promise as a plant growth regulator. Field trials conducted in 2023 indicated that it enhances crop yield by promoting root development and improving resistance to abiotic stressors such as drought and salinity. This dual functionality—simultaneously acting as an antioxidant and growth promoter—positions it as a valuable addition to sustainable agricultural practices.

The material science community has also taken interest in this compound due to its unique electronic properties. Researchers have incorporated it into organic semiconductors, where it serves as an electron acceptor material. A study published in Nature Communications highlighted its role in enhancing charge transport efficiency in polymer solar cells, leading to improved power conversion efficiencies (PCEs) of up to 12%. Such advancements underscore its potential for use in next-generation electronic devices.

In conclusion, 5-chloro-2-[(4-methylphenyl)methoxy]benzaldehyde, with its CAS number 590360-23-9, represents a multifaceted compound with diverse applications across various industries. Its chemical versatility, combined with recent breakthroughs in synthesis and application development, positions it as a key player in both academic research and industrial innovation. As ongoing studies continue to uncover new functionalities, this compound is poised to make significant contributions to fields ranging from medicine to renewable energy.

• 52803-69-7(2-(4-Chlorophenyl)methoxybenzoic Acid)
• 38544-16-0(2-(Benzyloxy)-5-chlorobenzaldehyde)
• 40359-59-9(2-(3-Chlorobenzyl)oxybenzaldehyde)
• 52803-75-5(2-(Benzyloxy)-5-chlorobenzoic Acid)
• 590376-26-4(5-chloro-2-[(3-methylphenyl)methoxy]benzaldehyde)
• 590360-24-0(5-chloro-2-[(2-methylphenyl)methoxy]benzaldehyde)
• 52803-76-6(5-Chloro-2-(4-chlorobenzyl)oxybenzoic Acid)
• 194802-96-5(2-[(3,4-dichlorophenyl)methoxy]benzaldehyde)
• 62176-34-5(5-Chloro-2-(3-chlorobenzyl)oxybenzoic Acid)
• 52803-59-5(2-[(4-chlorophenyl)methoxy]benzaldehyde)