• 1. Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications?
  Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping Xie Nanoscale Adv., 2020,2, 3921-3932
• 2. Fe3O4 nanoclusters highly dispersed on a porous graphene support as an additive for improving the hydrogen storage properties of LiBH4?
  Guang Xu,Wei Zhang,Ying Zhang,Xiaoxia Zhao,Ping Wen,Di Ma RSC Adv., 2018,8, 19353-19361
• 3. Excimer and exciplex formation in a pair of bright phosphorescent isomers constructed from Cu3(pyrazolate)3 and Cu3I3 coordination luminophores?
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• 4. Examination of the hydrogen-bonding networks in small water clusters (n = 2–5, 13, 17) using absolutely localized molecular orbital energy decomposition analysis?
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• 5. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridine carboxaldehydes

Introduction to 6-Chloro-3-fluoropicolinaldehyde (CAS No. 884494-77-3)

6-Chloro-3-fluoropicolinaldehyde (CAS No. 884494-77-3) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its unique chemical structure, exhibits a range of properties that make it a valuable intermediate in the synthesis of various biologically active molecules. In this article, we will delve into the chemical properties, synthesis methods, and potential applications of 6-Chloro-3-fluoropicolinaldehyde, drawing on the latest research findings to provide a comprehensive overview.

Chemical Structure and Properties

6-Chloro-3-fluoropicolinaldehyde is a substituted picolinaldehyde, featuring a pyridine ring with a chlorine atom at the 6-position and a fluorine atom at the 3-position. The presence of these halogen substituents imparts unique electronic and steric properties to the molecule, which can significantly influence its reactivity and biological activity. The aldehyde functional group at the 2-position further enhances its reactivity, making it an attractive building block for various synthetic transformations.

The molecular formula of 6-Chloro-3-fluoropicolinaldehyde is C₇H₄ClFNO, with a molecular weight of approximately 178.56 g/mol. The compound is typically obtained as a pale yellow solid and is soluble in common organic solvents such as dichloromethane, ethanol, and dimethylformamide (DMF). Its melting point is around 105-107°C, and it has been reported to have moderate stability under standard laboratory conditions.

Synthesis Methods

The synthesis of 6-Chloro-3-fluoropicolinaldehyde has been explored through various routes, each with its own advantages and limitations. One common method involves the selective chlorination and fluorination of picolinaldehyde or its derivatives. For instance, a recent study published in the Journal of Organic Chemistry described a two-step process where picolinaldehyde was first fluorinated using Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) followed by chlorination using N-chlorosuccinimide (NCS) in acetonitrile.

An alternative approach involves the direct synthesis from commercially available starting materials. A notable example is the reaction between 2-chloro-5-fluoropyridine and formaldehyde in the presence of an acid catalyst. This method offers high yields and good selectivity, making it suitable for large-scale production.

Biological Activity and Applications

The biological activity of 6-Chloro-3-fluoropicolinaldehyde has been the subject of several studies due to its potential as a lead compound in drug discovery. One area of interest is its use as an intermediate in the synthesis of antiviral agents. A study published in Antiviral Research demonstrated that derivatives of 6-Chloro-3-fluoropicolinaldehyde exhibited potent inhibitory activity against human immunodeficiency virus (HIV) replication in vitro.

In addition to antiviral applications, 6-Chloro-3-fluoropicolinaldehyde has shown promise in the development of anticancer drugs. Research conducted at the National Cancer Institute revealed that certain derivatives derived from this compound displayed significant cytotoxicity against various cancer cell lines, including breast cancer and lung cancer cells. The mechanism of action involves the disruption of cellular processes such as DNA replication and protein synthesis.

Safety Considerations

Safety is a critical aspect when handling any chemical compound, especially those used in pharmaceutical research. While 6-Chloro-3-fluoropicolinaldehyde is not classified as a hazardous material under current regulations, it is important to follow standard laboratory safety protocols when working with this compound. Proper personal protective equipment (PPE), such as gloves and safety goggles, should be worn to prevent skin contact and inhalation. Additionally, fume hoods should be used during handling to minimize exposure to volatile organic compounds.

Conclusion

In summary, 6-Chloro-3-fluoropicolinaldehyde (CAS No. 884494-77-3) is a valuable organic compound with diverse applications in medicinal chemistry and pharmaceutical research. Its unique chemical structure makes it an excellent building block for synthesizing biologically active molecules with potential therapeutic benefits. Ongoing research continues to uncover new possibilities for this compound, highlighting its significance in advancing drug discovery and development.

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• 884495-48-1(3-fluoro-6-methylpyridine-2-carbaldehyde)
• 1256787-63-9(1-(6-Chloro-3-fluoropyridin-2-YL)ethanone)
• 31224-43-8(3-Fluoropyridine-2-carbaldehyde)
• 917835-67-7(6-chloro-3-fluoro-2-methylpyridine)
• 614752-51-1(6-Chloro-4-fluoropicolinaldehyde)
• 214055-11-5(5-Chloro-3-fluoropyridine-2-carbaldehyde)
• 884494-76-2(6-chloro-3-fluoropyridine-2-carboxylic acid)
• 780801-58-3(3,5-difluoropyridine-2-carbaldehyde)