Production Method 1

1779-49-3

3512-17-2

885267-39-0

83261-73-8

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  48 h, rt → reflux; reflux → rt
1.2 Solvents: Tetrahydrofuran ;  rt; 48 h, rt

Reference

Regioselective alkyl transfer from phosphonium ylides to functionalized polyfluoroarenes

Lu, Wei; et al, Chemical Science, 2014, 5(5), 1934-1939

2,6-difluoro-4-methylpyridine Raw materials

• Methyltriphenylphosphonium bromide
• 2,4,6-Trifluoropyridine

2,6-difluoro-4-methylpyridine Preparation Products

• 2,4-Difluoro-6-methylpyridine (83261-73-8)
• 2,6-difluoro-4-methylpyridine (885267-39-0)

• 1. Evolution of calcium phosphate precipitation in hanging drop vapor diffusion by in situRaman microspectroscopy
  Gloria Belén Ramírez-Rodríguez,José Manuel Delgado-López,Jaime Gómez-Morales CrystEngComm, 2013,15, 2206-2212
• 2. Excellent electrochemical performance of LiFe0.4Mn0.6PO4 microspheres produced using a double carbon coating process?
  Yong Ping Huang,Tao Tao,Zheng Chen,Wei Han,Ying Wu,Chunjiang Kuang,Shaoxiong Zhou,Ying Chen J. Mater. Chem. A, 2014,2, 18831-18837
• 3. Excimer and exciplex formation in a pair of bright phosphorescent isomers constructed from Cu3(pyrazolate)3 and Cu3I3 coordination luminophores?
  Shun-Ze Zhan,Mian Li,Xiao-Ping Zhou,Dan Li,Seik Weng Ng RSC Adv., 2011,1, 1457-1459
• 4. Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions
  Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. Chalmers Analyst, 2005,130, 514-527
• 5. Fate of Sb(v) and Sb(iii) species along a gradient of pH and oxygen concentration in the Carnoulès mine waters (Southern France)
  Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique Desoeuvre Environ. Sci.: Processes Impacts, 2013,15, 1536-1544

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Halopyridines Polyhalopyridines

Recent Advances in the Application of 2,6-Difluoro-4-methylpyridine (CAS: 885267-39-0) in Chemical Biology and Pharmaceutical Research

The compound 2,6-difluoro-4-methylpyridine (CAS: 885267-39-0) has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This heterocyclic compound, characterized by its fluorine substitutions and methyl group, serves as a critical building block in the synthesis of various bioactive molecules. Recent studies have highlighted its role in the development of novel drug candidates, particularly in the fields of oncology, neurology, and infectious diseases. The unique electronic properties imparted by the fluorine atoms enhance the compound's reactivity and binding affinity, making it a valuable scaffold for medicinal chemistry.

One of the most notable applications of 2,6-difluoro-4-methylpyridine is its use in the synthesis of kinase inhibitors. Kinases are pivotal targets in cancer therapy, and the incorporation of this pyridine derivative has been shown to improve the selectivity and potency of inhibitors. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of 2,6-difluoro-4-methylpyridine exhibited nanomolar inhibitory activity against specific tyrosine kinases, with minimal off-target effects. This finding underscores the compound's potential in designing next-generation anticancer agents.

In addition to its role in oncology, 2,6-difluoro-4-methylpyridine has been explored for its utility in central nervous system (CNS) drug discovery. The fluorine atoms contribute to the compound's ability to cross the blood-brain barrier (BBB), a critical feature for CNS-active drugs. Recent research has focused on modifying the pyridine core to enhance its pharmacokinetic properties, such as metabolic stability and solubility. A 2022 study in ACS Chemical Neuroscience reported the successful development of a series of neuroprotective agents based on this scaffold, showing promising results in preclinical models of neurodegenerative diseases.

Another emerging area of interest is the use of 2,6-difluoro-4-methylpyridine in the design of antimicrobial agents. The rise of antibiotic-resistant pathogens has necessitated the discovery of new chemical entities with novel mechanisms of action. Researchers have leveraged the electrophilic nature of the fluorine atoms to create derivatives that disrupt bacterial cell wall synthesis or inhibit essential enzymes. A recent publication in Bioorganic & Medicinal Chemistry Letters highlighted the efficacy of such derivatives against multidrug-resistant Staphylococcus aureus, suggesting their potential as lead compounds for further development.

The synthetic versatility of 2,6-difluoro-4-methylpyridine also extends to its use in radiopharmaceuticals. Fluorine-18 labeled derivatives of this compound have been investigated as positron emission tomography (PET) tracers for imaging applications. A 2023 study in the Journal of Nuclear Medicine detailed the synthesis and evaluation of a fluorine-18 labeled analog, which demonstrated high target specificity and favorable biodistribution in vivo. This advancement opens new avenues for non-invasive diagnostic tools in oncology and neurology.

Despite these promising developments, challenges remain in the large-scale synthesis and optimization of 2,6-difluoro-4-methylpyridine-based compounds. Issues such as regioselectivity in fluorination reactions and the need for greener synthetic methodologies are areas of active research. Recent efforts have focused on catalytic fluorination techniques and flow chemistry to address these limitations, as reported in a 2023 review in Chemical Reviews.

In conclusion, 2,6-difluoro-4-methylpyridine (CAS: 885267-39-0) continues to be a cornerstone in chemical biology and pharmaceutical research. Its multifaceted applications in drug discovery, radiopharmaceuticals, and antimicrobial agents highlight its enduring relevance. Future research is expected to further elucidate its potential, particularly in addressing unmet medical needs and advancing precision medicine.

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