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  Zhixia Liu,Tingjian Chen,Floyd E. Romesberg Chem. Sci., 2017,8, 8179-8182
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenol ethers Aminophenyl ethers
• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides

Introduction to 2-Chloro-3-methoxyaniline (CAS No. 113206-03-4)

2-Chloro-3-methoxyaniline, identified by the Chemical Abstracts Service Number (CAS No.) 113206-03-4, is a significant intermediate in the field of organic synthesis and pharmaceutical chemistry. This compound belongs to the class of aniline derivatives, characterized by the presence of both chloro and methoxy functional groups on a benzene ring. The strategic positioning of these substituents imparts unique reactivity, making it a valuable building block for the synthesis of more complex molecules.

The structure of 2-Chloro-3-methoxyaniline consists of a benzene ring substituted at the 2-position with a chlorine atom and at the 3-position with a methoxy group. This arrangement creates a molecule with distinct electronic properties, influenced by the electron-withdrawing nature of the chloro group and the electron-donating effect of the methoxy group. Such structural features make it particularly useful in cross-coupling reactions, such as Suzuki-Miyaura and Buchwald-Hartwig couplings, which are fundamental in constructing biaryl systems prevalent in many pharmaceuticals.

In recent years, 2-Chloro-3-methoxyaniline has garnered attention in the development of novel therapeutic agents. Its derivatives have been explored as intermediates in the synthesis of kinase inhibitors, which play a crucial role in targeting various cancers and inflammatory diseases. For instance, modifications of this scaffold have led to compounds with potent activity against tyrosine kinases, demonstrating promising preclinical results. The ability to fine-tune the electronic and steric properties of the molecule through further functionalization allows for the optimization of drug-like characteristics such as solubility, bioavailability, and metabolic stability.

The pharmaceutical industry has also leveraged 2-Chloro-3-methoxyaniline in the synthesis of antimicrobial agents. Researchers have reported its utility in creating novel quinolone analogs, which exhibit enhanced efficacy against resistant bacterial strains. The chloro and methoxy groups facilitate further derivatization into more complex heterocyclic structures, enabling access to compounds with improved pharmacokinetic profiles. This adaptability underscores the compound's versatility as a synthetic precursor.

Moreover, 2-Chloro-3-methoxyaniline finds applications in materials science, particularly in the development of organic electronic materials. Its derivatives have been incorporated into organic light-emitting diodes (OLEDs) and field-effect transistors (OFETs) due to their ability to form stable conjugated systems. The presence of both electron-withdrawing and donating groups allows for fine control over charge transport properties, making it an attractive candidate for optimizing device performance.

From a synthetic chemistry perspective, 2-Chloro-3-methoxyaniline serves as a key intermediate in multi-step syntheses. Its preparation typically involves chlorination and methylation reactions on aniline precursors, processes that highlight its importance in industrial-scale organic synthesis. Advances in catalytic methods have further refined its production, enabling greener and more efficient routes to this valuable compound.

The biological activity of 2-Chloro-3-methoxyaniline and its derivatives continues to be an area of active investigation. Studies have revealed its potential role as a modulator of enzyme activity, particularly in pathways relevant to neurodegenerative diseases. By serving as a scaffold for structure-activity relationship (SAR) studies, researchers can identify new pharmacophores that may lead to breakthrough treatments for conditions such as Alzheimer's and Parkinson's disease.

In conclusion, 2-Chloro-3-methoxyaniline (CAS No. 113206-03-4) is a multifaceted compound with broad applications across pharmaceuticals, materials science, and organic synthesis. Its unique structural features enable diverse functionalization strategies, making it indispensable in drug discovery and material development. As research progresses, continued exploration of its derivatives promises to yield novel compounds with significant therapeutic and technological implications.

• 85893-87-4(2-Chloro-3-methoxyaniline hydrochloride)
• 105945-25-3(Benzenamine,3-(2-chlorophenoxy)-)
• 526217-43-6(Phenol, 3-amino-2-chloro-6-methoxy-)
• 846031-58-1(Benzenamine,2-chloro-3-ethoxy-)
• 379229-30-8(2,4-Dichloro-5-methoxyaniline hydrochloride)
• 85006-21-9(2-Chloro-5-methoxyaniline hydrochloride)
• 98446-49-2(2,4-Dichloro-5-methoxyaniline)
• 13726-14-2(4-Chloro-3-methoxyaniline)
• 2401-24-3(2-Chloro-5-methoxyaniline)
• 120758-03-4(2-Chloro-3,5-dimethoxyaniline)