Production Method 1

626-05-1

175422-04-5

98027-81-7

Reaction Conditions

1.1R:F3CCO2H, R:H2O2, rt; overnight, reflux
1.2R:H2O
1.3R:NaHCO3, S:H2O, neutralized
2.1R:H2SO4, R:HNO3, 0°C; overnight, 90°C

Reference

A strong hydride donating, acid stable and reusable 1,4-dihydropyridine for selective aldimine and aldehyde reductions

By Hirao, Yasukazu et al, Organic & Biomolecular Chemistry, 1671, 20(8), 1671-1679

Production Method 2

626-05-1

175422-04-5

98027-81-7

Reaction Conditions

1.1R:F3CCO2H, R:H2O2, S:H2O, overnight, reflux
1.2R:H2O
2.1R:H2SO4, R:HNO3, 0°C; 5 h, 90°C

Reference

Interaction of the dihydropyridine/pyridinium redox pair fixed into a V-shaped conformation

By Hirao, Yasukazu et al, Heterocycles, 1345, 98(10), 1345-1353

2,6-Dibromo-4-nitropyridine Raw materials

• 2,6-Dibromopyridine

2,6-Dibromo-4-nitropyridine Preparation Products

• 2,6-Dibromo-4-nitropyridine (175422-04-5)
• 2,6-Dibromo-4-nitropyridine oxide (98027-81-7)

• 1. Homoleptic and heteroleptic iron(II) and ruthenium(II) complexes of novel 4′-nitro-2,2′:6′,2″-terpyridines and 4′-amino-2,2′:6′,2″-terpyridines
  Reza-Ali Fallahpour,Markus Neuburger,Magareta Zehnder New J. Chem. 1999 23 53
• 2. Homoleptic and heteroleptic iron(II) and ruthenium(II) complexes of novel 4′-nitro-2,2′:6′,2″-terpyridines and 4′-amino-2,2′:6′,2″-terpyridines
  Reza-Ali Fallahpour,Markus Neuburger,Magareta Zehnder New J. Chem. 1999 23 53
• 3. Luminescent (metallo-supramolecular) cross-linked lanthanide hydrogels from a btp (2,3-bis(1,2,3-triazol-4-yl)picolinamide) monomer give rise to strong Tb(iii) and Eu(iii) centred emissions
  Isabel N. Hegarty,Samuel J. Bradberry,June I. Lovitt,Jason M. Delente,Niamh Willis-Fox,Ronan Daly,Thorfinnur Gunnlaugsson Mater. Chem. Front. 2023 7 906
• 4. Highly efficient stabilisation of meta-ethynylpyridine polymers with amide side chains in water by coordination of rare-earth metals
  Hiroki Makida,Hajime Abe,Masahiko Inouye Org. Biomol. Chem. 2015 13 1700
• 5. “Off-on” aggregation-based fluorescent sensor for the detection of chloride in water
  Michelle M. Watt,Jeffrey M. Engle,Kurtis C. Fairley,Timothy E. Robitshek,Michael M. Haley,Darren W. Johnson Org. Biomol. Chem. 2015 13 4266

• Solvents and Organic Chemicals Organic Compounds Organic 1,3-dipolar compounds Allyl-type 1,3-dipolar organic compounds C-nitro compounds
• Solvents and Organic Chemicals Organic Compounds Organic 1,3-dipolar compounds Allyl-type 1,3-dipolar organic compounds Organic nitro compounds C-nitro compounds

Professional Introduction to 2,6-Dibromo-4-nitropyridine (CAS No. 175422-04-5)

2,6-Dibromo-4-nitropyridine, with the chemical formula C?H?Br?N?O? and CAS number 175422-04-5, is a significant intermediate in modern chemical synthesis and pharmaceutical research. This compound has garnered considerable attention due to its versatile applications in the development of novel agrochemicals, pharmaceuticals, and specialty chemicals. Its unique structural properties, characterized by the presence of both bromine and nitro substituents on a pyridine core, make it a valuable building block for further functionalization and derivatization.

The< strong>2,6-Dibromo-4-nitropyridine molecule exhibits a high degree of reactivity, which is primarily attributed to the electron-withdrawing nature of the nitro group and the electron-donating effects of the bromine atoms. This balance of electronic properties allows for a wide range of chemical transformations, including nucleophilic substitution, metal-catalyzed coupling reactions, and palladium-catalyzed cross-coupling reactions. These reactions are crucial in constructing complex molecular architectures, which are often required in the synthesis of biologically active compounds.

In recent years, there has been a surge in research focused on developing new methodologies for the functionalization of heterocyclic compounds such as< strong>pyridine derivatives. Among these derivatives, 2,6-Dibromo-4-nitropyridine has emerged as a particularly useful precursor due to its ability to undergo various transformations that yield highly functionalized products. For instance, palladium-catalyzed Suzuki-Miyaura coupling reactions have been extensively explored for introducing aryl or vinyl groups at the positions adjacent to the bromine atoms. These modifications have led to the synthesis of novel compounds with potential applications in medicinal chemistry.

The pharmaceutical industry has shown particular interest in< strong>2,6-Dibromo-4-nitropyridine as a scaffold for drug discovery. Its structural motif is found in several bioactive molecules that exhibit antimicrobial, antiviral, and anticancer properties. Researchers have leveraged its reactivity to develop libraries of substituted pyridines that can be screened for biological activity. Notably, studies have demonstrated that modifications at the 2- and 6-positions can significantly influence the pharmacokinetic properties of derived compounds. This has spurred efforts to optimize synthetic routes for higher yields and better purity profiles.

In agrochemical research, 2,6-Dibromo-4-nitropyridine has been utilized as an intermediate in the synthesis of herbicides and pesticides. The presence of bromine and nitro groups enhances its binding affinity to biological targets in plants and pests. Recent advances in green chemistry have prompted investigations into more sustainable synthetic pathways for this compound. For example, catalytic methods that minimize waste and reduce energy consumption are being actively developed. Such approaches align with global efforts to promote environmentally friendly chemical processes.

The role of computational chemistry in designing efficient synthetic strategies for< strong>2,6-Dibromo-4-nitropyridine cannot be overstated. Molecular modeling techniques have enabled researchers to predict reaction outcomes with high accuracy before conducting experimental trials. This has not only saved time but also reduced costs associated with trial-and-error synthesis. Additionally, machine learning algorithms are being employed to identify optimal reaction conditions based on large datasets generated from high-throughput experiments.

The versatility of< strong>2,6-Dibromo-4-nitropyridine extends beyond pharmaceuticals and agrochemicals. It is also used in materials science for the development of organic electronic components such as light-emitting diodes (OLEDs) and photovoltaic cells. The electron-deficient nature of the nitro group makes it an attractive moiety for tuning electronic properties in conjugated polymers. Researchers have reported significant improvements in device performance by incorporating< strong>pyridine derivatives, including this compound, into their formulations.

The future prospects for< strong>2,6-Dibromo-4-nitropyridine are promising as new synthetic methodologies continue to emerge. Advances in flow chemistry and continuous manufacturing are expected to further enhance its accessibility and scalability. Furthermore, collaborations between academia and industry are likely to drive innovation by combining expertise from different disciplines. As our understanding of molecular interactions deepens, so too will our ability to harness this compound's potential for creating novel materials and drugs.

In conclusion,< strong>2,6-Dibromo-4-nitropyridine (CAS No. 175422-04-5) represents a cornerstone in modern chemical synthesis with far-reaching implications across multiple industries. Its unique reactivity profile makes it an indispensable tool for researchers seeking to develop innovative solutions in pharmaceuticals, agrochemicals, and materials science. As scientific knowledge evolves and new technologies emerge,< strong>this compound's role is poised to expand even further.

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