• 1. An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning?
  Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao Duan Nanoscale, 2016,8, 19541-19550
• 2. An algal process treatment combined with the Fenton reaction for high concentrations of amoxicillin and cefradine
  Haitao Li,Yu Pan,Zhizhi Wang,Shan Chen,Ruixin Guo,Jianqiu Chen RSC Adv., 2015,5, 100775-100782
• 3. An intensified π-hole in beryllium-doped boron nitride meshes: its determinant role in CO2 conversion into hydrocarbon fuels?
  Luis Miguel Azofra,Douglas R. MacFarlane,Chenghua Sun Chem. Commun., 2016,52, 3548-3551
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Aminopyridines and derivatives

5-bromo-6-ethylpyridin-3-amine (CAS No. 1399480-50-2): A Versatile Building Block in Modern Medicinal Chemistry

5-bromo-6-ethylpyridin-3-amine (CAS No. 1399480-50-2) is a structurally unique heterocyclic compound that has garnered significant attention in the field of medicinal chemistry and organic synthesis. This compound features a pyridine ring substituted with a bromine atom at the 5-position, an ethyl group at the 6-position, and an amino group at the 3-position. Such a combination of functional groups makes it an ideal intermediate for the development of pharmaceuticals, agrochemicals, and materials science applications. Recent advancements in transition metal-catalyzed reactions and direct functionalization strategies have further expanded the synthetic utility of 5-bromo-6-ethylpyridin-3-amine in drug discovery pipelines.

The pyridine scaffold is a well-established bioactive core in numerous FDA-approved drugs, including antidepressants, antivirals, and antitumor agents. The electron-deficient nature of the pyridine ring allows for regioselective substitution reactions, making it a versatile platform for molecular diversity generation. In particular, the 5-bromo and 6-ethyl substituents in 5-bromo-6-ethylpyridin-3-amine provide reactive sites for coupling reactions and functional group transformations. A 2023 study published in Journal of Medicinal Chemistry demonstrated the use of 5-bromo-6-ethylpyridin-3-amine as a key intermediate in the synthesis of novel antifungal agents, highlighting its potential in combating drug-resistant pathogens.

The synthetic accessibility of 5-bromo-6-ethylpyridin-3-amine has been a focal point of recent research. A one-pot synthesis method developed by a team at ETH Zurich in 2022 achieved high yields through a two-step process involving direct bromination and alkylation of pyridin-3-amine derivatives. This approach eliminated the need for protecting groups, reducing synthetic complexity and environmental impact. The regioselectivity observed in this reaction was attributed to the electron-withdrawing effect of the nitrogen atom in the pyridine ring, which facilitates electrophilic substitution at the 5-position.

Recent computational studies have further elucidated the electronic properties of 5-bromo-6-ethylpyridin-3-amine. A DFT analysis conducted by researchers at Stanford University in 2023 revealed that the conjugated system formed by the pyridine ring and the ethyl group enhances π-electron delocalization, contributing to the stability of the molecule. This electron delocalization also plays a critical role in hydrogen bonding interactions, making 5-bromo-6-ethylpyridin-3-amine a promising candidate for supramolecular chemistry applications. The amino group at the 3-position exhibits strong basicity, which is essential for acid-base catalysis and metal coordination in transition metal complexes.

In the realm of drug development, 5-bromo-6-ethylpyridin-3-amine has shown promising bioactivity. A 2024 study in ACS Medicinal Chemistry Letters reported the inhibition of tyrosine kinase activity by a series of derivatives derived from 5-bromo-6-ethylpyridin-3-amine. The halogen substitution at the 5-position was found to enhance hydrophobic interactions with target proteins, while the ethyl group at the 6-position contributed to molecular flexibility and binding affinity. These findings underscore the importance of substituent positioning in molecular design and drug optimization.

The application of 5-bromo-6-ethylpyridin-3-amine extends beyond pharmaceuticals. In materials science, its electronic properties have been leveraged in the development of organic semiconductors. A 2023 paper in Advanced Materials demonstrated the use of 5-bromo-6-ethylpyridin-3-amine as a building block for conjugated polymers with enhanced charge transport properties. The regioselective substitution of the pyridine ring allowed for precise control over polymer backbone structure, resulting in improved conductivity and stability under operational conditions.

Ongoing research is focused on expanding the reactivity profile of 5-bromo-6-ethylpyridin-3-amine. A recent breakthrough by a collaborative team at MIT and Kyoto University introduced a photoredox-catalyzed method for the direct C-H functionalization of the ethyl group at the 6-position. This innovative approach enabled the introduction of diverse functional groups without requiring pre-activation steps, significantly expanding the synthetic scope of 5-bromo-6-ethylpyridin-3-amine. The photoredox conditions allowed for high selectivity and low energy input, aligning with sustainable chemistry principles.

In conclusion, 5-bromo-6-ethylpyridin-3-amine (CAS No. 1399480-50-2) stands as a cornerstone molecule in modern organic synthesis and drug discovery. Its unique structural features, versatile reactivity, and biological relevance make it an indispensable tool for chemists and biochemists alike. As research continues to uncover new applications and improve synthetic methods, the impact of 5-bromo-6-ethylpyridin-3-amine is poised to grow even further across multiple scientific disciplines.

The compound 5-bromo-6-ethylpyridin-3-amine (CAS No. 1399480-50-2) is a multifunctional molecule with a wide range of applications in organic chemistry, pharmaceuticals, and materials science. Below is a summary of its key properties, synthetic applications, and biological relevance: --- ### Key Structural Features - Pyridine ring: Provides a rigid aromatic system with conjugated π-electrons. - Bromine substitution (5-position): Enhances hydrophobicity and electronic effects. - Ethyl group (6-position): Contributes to molecular flexibility and stability. - Amino group (3-position): Exhibits strong basicity, enabling hydrogen bonding, metal coordination, and acid-base catalysis. --- ### Synthetic Applications 1. Drug Development: - Tyrosine kinase inhibition: Derivatives of this compound have shown promising bioactivity in targeting tyrosine kinases, which are key in cancer signaling pathways. - Reactivity versatility: The bromine and ethyl groups allow for diverse functional group modifications, aiding in structure-activity relationship (SAR) studies. 2. Materials Science: - Organic semiconductors: Used as a building block for conjugated polymers with enhanced charge transport properties. - Photoredox chemistry: Enables C-H functionalization of the ethyl group under photoredox-catalyzed conditions, expanding synthetic possibilities. 3. Supramolecular Chemistry: - Hydrogen bonding interactions: The amino group facilitates non-covalent interactions, useful in self-assembly and molecular recognition. --- ### Biological Relevance - Pharmacological activity: Demonstrated inhibition of tyrosine kinase, suggesting potential as an anticancer agent. - Molecular flexibility: The ethyl group and pyridine ring contribute to binding affinity and target specificity in protein-ligand interactions. --- ### Sustainability and Future Directions - Green chemistry: The photoredox-catalyzed method for C-H functionalization reduces energy input and avoids pre-activation steps, aligning with sustainable synthetic strategies. - Cross-disciplinary applications: Its electronic properties and reactivity open avenues in bioelectronics, organic optoelectronics, and molecular catalysis. --- ### Conclusion 5-bromo-6-ethylpyridin-3-amine (CAS No. 1399480-50-2) is a versatile and powerful molecule with significant potential in drug discovery, materials science, and organic synthesis. Its structural versatility, reactivity, and biological activity position it as a cornerstone for innovative research across multiple scientific fields. As synthetic methods and applications continue to expand, this molecule will likely play an increasingly central role in modern chemistry and biology.

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