• 1. An amphipathic trans-acting phosphorothioate RNA element delivers an uncharged phosphorodiamidate morpholino sequence in mdx mouse myotubes?
  H. V. Jain,D. Verthelyi,S. L. Beaucage RSC Adv., 2017,7, 42519-42528
• 2. An atomistic mechanism for the degradation of perovskite solar cells by trapped charge?
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• 3. An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system?
  Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai Zhang RSC Adv., 2014,4, 49995-50002
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Aniline and substituted anilines 2-bromoanilines

2,6-Dibromo-3-fluoro-phenylamine: A Comprehensive Overview of CAS No. 1691609-18-3

2,6-Dibromo-3-fluoro-phenylamine (CAS No. 1691609-18-3) 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 bromine and fluorine substituents, offers a range of applications in the development of novel pharmaceuticals and advanced materials. This article delves into the chemical properties, synthesis methods, and potential applications of 2,6-Dibromo-3-fluoro-phenylamine, highlighting recent advancements and future prospects.

Chemical Properties

2,6-Dibromo-3-fluoro-phenylamine is a white crystalline solid with a molecular formula of C₆H₃Br₂FNH₂. The presence of bromine and fluorine atoms imparts unique electronic and steric properties to the molecule, making it an attractive building block for various chemical syntheses. The compound exhibits good solubility in common organic solvents such as dichloromethane, dimethylformamide (DMF), and dimethyl sulfoxide (DMSO). Its melting point is reported to be around 150°C, and it has a relatively low vapor pressure at room temperature.

Synthesis Methods

The synthesis of 2,6-Dibromo-3-fluoro-phenylamine can be achieved through several routes, each with its own advantages and limitations. One common method involves the bromination of 3-fluorophenylamine followed by selective bromination at the 2-position. Another approach involves the nucleophilic substitution of 2,6-dibromofluorobenzene with ammonia or an amine derivative. Recent advancements in green chemistry have led to the development of more environmentally friendly synthesis methods, such as using microwave-assisted reactions or catalytic systems to improve yield and reduce by-products.

Applications in Medicinal Chemistry

2,6-Dibromo-3-fluoro-phenylamine has shown promise in the development of novel pharmaceuticals due to its ability to modulate biological targets. Studies have demonstrated its potential as a lead compound for the design of drugs targeting various diseases. For instance, researchers have explored its use in the development of anticancer agents by incorporating it into small molecules that can selectively inhibit cancer cell growth. Additionally, its unique electronic properties make it suitable for designing compounds that can cross the blood-brain barrier, opening up possibilities for treating neurological disorders.

Potential in Materials Science

Beyond medicinal applications, 2,6-Dibromo-3-fluoro-phenylamine has found utility in materials science. Its bromine and fluorine substituents contribute to its stability and reactivity, making it a valuable precursor for the synthesis of functional polymers and organic semiconductors. Recent research has focused on using this compound to develop materials with enhanced electronic properties for use in organic light-emitting diodes (OLEDs) and solar cells. The ability to fine-tune the electronic structure through chemical modifications further expands its potential applications in advanced materials.

Recent Research Findings

The scientific community continues to uncover new insights into the properties and applications of 2,6-Dibromo-3-fluoro-phenylamine. A study published in the Journal of Medicinal Chemistry highlighted its role as a scaffold for developing potent inhibitors of protein kinases, which are key targets in cancer therapy. Another study in Advanced Materials explored its use as a building block for creating high-performance organic semiconductors with improved charge transport properties.

Safety Considerations

In handling 2,6-Dibromo-3-fluoro-phenylamine, it is important to adhere to standard safety protocols for handling organic compounds. While it is not classified as a hazardous material under current regulations, proper personal protective equipment (PPE) should be used to minimize exposure risks. Laboratory personnel should be trained in safe handling practices and be aware of potential health effects associated with prolonged exposure.

Conclusion

2,6-Dibromo-3-fluoro-phenylamine (CAS No. 1691609-18-3) is a multifaceted compound with significant potential in both medicinal chemistry and materials science. Its unique chemical structure provides a foundation for developing novel pharmaceuticals and advanced materials with enhanced properties. As research continues to advance, the applications of this compound are likely to expand further, contributing to breakthroughs in various scientific fields.

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