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  Sowmyalakshmi Venkataraman RSC Adv., 2015,5, 73807-73813
• 2. Distinct impact of glycation towards the aggregation and toxicity of murine and human amyloid-β?
  Eunju Nam,Jiyeon Han,Sunhee Choi,Mi Hee Lim Chem. Commun., 2021,57, 7637-7640
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  Guiying Zhang,Maosheng Cheng,Yanni Li,Keliang Liu,Lifeng Cai Chem. Commun., 2013,49, 11086-11088
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzopyrazoles Indazoles

3-Bromo-4-Fluoro-1-Methyl-1H-Indazole: A Comprehensive Overview

The compound with CAS No. 1260769-89-8, commonly referred to as 3-bromo-4-fluoro-1-methyl-1H-indazole, is a highly specialized organic compound that has garnered significant attention in the fields of medicinal chemistry, materials science, and synthetic organic chemistry. This compound belongs to the indazole family, a class of heterocyclic aromatic compounds known for their unique electronic properties and versatile applications. The structure of 3-bromo-4-fluoro-1-methyl-1H-indazole features a fused bicyclic system with nitrogen and oxygen atoms, along with substituents at the 3 and 4 positions that confer distinct chemical reactivity and biological activity.

Recent advancements in synthetic methodologies have enabled the efficient synthesis of 3-bromo-4-fluoro-1-methyl-1H-indazole through various routes, including microwave-assisted synthesis and catalytic cross-coupling reactions. These methods have not only improved the yield and purity of the compound but also opened new avenues for its application in drug discovery and material development. For instance, researchers have explored the use of this compound as a building block in the construction of bioactive molecules targeting various disease states, including cancer and neurodegenerative disorders.

In terms of biological activity, 3-bromo-4-fluoro-1-methyl-1H-indazole has demonstrated promising results in preclinical studies. Its ability to modulate key cellular pathways, such as kinase activity and receptor signaling, makes it a valuable lead compound for drug development. Furthermore, the compound's unique electronic properties have been leveraged in the design of advanced materials, including organic semiconductors and optoelectronic devices.

From a structural perspective, the presence of bromine and fluorine substituents at the 3 and 4 positions introduces significant steric and electronic effects into the molecule. These effects influence its reactivity in various chemical transformations, such as nucleophilic aromatic substitution and cross-coupling reactions. Recent studies have highlighted the importance of these substituents in tuning the compound's solubility, stability, and bioavailability, which are critical factors in drug design.

The synthesis of 3-bromo-4-fluoro-1-methyl-1H-indazole typically involves a multi-step process that begins with the preparation of an indazole core followed by functionalization at specific positions. One notable approach involves the use of palladium-catalyzed coupling reactions to introduce halogen substituents at desired positions. This method not only ensures high regioselectivity but also facilitates the incorporation of other functional groups into the molecule.

In addition to its role in medicinal chemistry, 3-bromo-4-fluoro-1-methyl-1H-indazole has found applications in materials science. Its aromaticity and conjugated system make it an ideal candidate for use in organic electronics. Recent research has focused on its potential as a component in light-emitting diodes (LEDs) and solar cells, where its electronic properties contribute to enhanced device performance.

Looking ahead, the continued exploration of 3-bromo-4-fluoro-1-methyl-1H-indazole is expected to yield further insights into its chemical behavior and biological activity. As researchers refine synthetic methods and uncover new applications for this compound, it is poised to play an increasingly important role in both academic research and industrial development.

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