Production Method 1

626-05-1

98027-81-7

175422-04-5

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

25373-69-7

98027-81-7

Reaction Conditions

1.1R:H2SO4, R:HNO3, 22 h, 60°C; 60°C → rt
1.2R:NH4Cl, S:H2O, cooled

Reference

A MOF platform for incorporation of complementary organic motifs for CO2 binding

By Deria, Pravas et al, Chemical Communications (Cambridge, 1247, 51(62), 12478-12481

Production Method 3

626-05-1

98027-81-7

Reaction Conditions

1.1R:H2O2, S:H2O, S:F3CCO2H, 80°C; 4 h, 80°C
2.1R:H2SO4, R:HNO3, 90°C; 2 h, 90°C

Reference

Synthesis and characterization of highly stable and efficient star-molecules

By Huang, Hai-Fang et al, Dyes and Pigments, 2013, 96(3), 705-713

Production Method 4

626-05-1

98027-81-7

Reaction Conditions

1.1R:H2O2, S:H2O, S:F3CCO2H, 3 h, 42°C; 42°C → rt
1.2R:H2O, rt → -5°C
1.3R:Disodium carbonate, neutralized
2.1R:HNO3 ?NO2, R:H2SO4, S:H2O, rt → 90°C; 2 h, 90°C; cooled
2.2R:H2O, cooled

Reference

Preparation of 2,6-dibromo-4-aminopyridine

By Niu, Qian-qian et al, Fenzi Kexue Xuebao, 2006, 22(6), 401-404

Production Method 5

626-05-1

98027-81-7

175422-04-5

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

Production Method 6

626-05-1

98027-81-7

Reaction Conditions

1.1R:F3CCO2H, R:H2O2, S:H2O, 4 h, 90°C; 90°C → rt
1.2S:H2O, 3 h, 0°C
1.3R:Disodium carbonate, 0°C, neutralized
2.1R:H2SO4, rt
2.2R:H2SO4, R:HNO3, rt → 80°C; 25 min, 80°C; 3.5 h, 80°C; 80°C → rt
2.3R:H2O, 0°C

Reference

Access to 3-Deazaguanosine Building Blocks for RNA Solid-Phase Synthesis Involving Hartwig-Buchwald C-N Cross-Coupling

By Mairhofer, Elisabeth et al, Organic Letters, 3900, 21(11), 3900-3903

Production Method 7

626-05-1

98027-81-7

Reaction Conditions

1.1R:F3CCO2H, R:H2O2, R:O(C(=O)CF3)2, S:H2O, 80°C; 4 h, 80°C
2.1R:HNO3 ?NO2, R:H2SO4, 90°C; 2 h, 90°C

Reference

Synthesis of Hyperbranched Polypyridine via a Cross Coupling Approach as an n-type π-Conjugated Polymer

By Koga, Takashi et al, Macromolecular Chemistry and Physics, 2017, 218(22),

Production Method 8

626-05-1

98027-81-7

Reaction Conditions

1.1R:F3CCO2H, R:H2O2
2.1R:H2SO4, R:HNO3

Reference

Process Development and Crystallization in Oiling-Out System of a Novel Topical Antiandrogen

By Daver, Sebastien et al, Organic Process Research & Development, 2017, 21(2), 231-240

Production Method 9

626-05-1

98027-81-7

Reaction Conditions

1.1R:F3CCO2H, R:H2O2, S:H2O, rt; 12 h, 100°C
2.1R:H2SO4, R:HNO3, 0°C; 12 h, 60°C
2.2R:NaHCO3, S:H2O, 0°C

Reference

Inhibition of Cancer-Associated Mutant Isocitrate Dehydrogenases: Synthesis, Structure-Activity Relationship, and Selective Antitumor Activity

By Liu, Zhen et al, Journal of Medicinal Chemistry, 8307, 57(20), 8307-8318

Production Method 10

626-05-1

98027-81-7

Reaction Conditions

1.1R:H2NC(=O)NH2 ?H2O2, R:O(C(=O)CF3)2, S:CH2Cl2, rt → 5°C; 45 min, 5-7°C; 7°C → rt; 20 h, rt; rt → 10°C
1.2R:Na2SO4, S:H2O, 60 min, 10°C
2.1R:H2SO4, R:HNO3, rt; rt → 79°C; 25 min, 79°C; 3.5 h, 83-85°C; 85°C → rt

Reference

A flexible synthesis of C-6 and N-1 analogues of a 4-amino-1,3-dihydroimidazo[4,5-c]pyridin-2-one core

By Hay, Duncan A. et al, Tetrahedron Letters, 5728, 52(44), 5728-5732

Production Method 11

626-05-1

98027-81-7

Reaction Conditions

1.1R:F3CCO2H, R:H2O2, S:H2O, 1 h, 35°C; 35°C → rt
1.2R:Disodium carbonate, S:H2O, pH 9
2.1R:HNO3 ?NO2, R:H2SO4, S:H2O, rt → 80°C; 1 h, 80°C

Reference

Process for preparation of 2,6-bis[3-(aminomethyl)-1-pyrazolyl]pyridine derivative as chelant used in homogeneous time-resolved fluorescence immunoassay

By Pan, Lihua et al, Faming Zhuanli Shenqing, 1012, ,

Production Method 12

626-05-1

98027-81-7

Reaction Conditions

1.1R:F3CCO2H, R:H2O2, S:H2O, 3 h, 42°C; 42°C → rt
1.2R:Disodium carbonate, S:H2O, basify
2.1R:H2SO4, R:HNO3, S:H2O, rt → 90°C; 2 h, 90°C

Reference

Synthesis of 2,6-bis(3-methyl-1H-pyrazol-1-yl)-4-aminopyridine

By Li, Zhen et al, Huaxue Yanjiu, 2007, 18(1), 43-45

Production Method 13

626-05-1

98027-81-7

Reaction Conditions

1.1R:H2O2, S:H2O, S:F3CCO2H, 1 h; 4 h, 95-100°C
2.1R:HNO3 ?NO2, R:H2SO4, 20 h, 60°C
2.2R:NH4OH, S:H2O, neutralized

Reference

The Development of a Practical and Reliable Large-Scale Synthesis of 2,6-Diamino-4-bromopyridine

By Nettekoven, Matthias and Jenny, Christian, Organic Process Research & Development, 2003, 7(1), 38-43

Production Method 14

626-05-1

98027-81-7

Reaction Conditions

1.1R:F3CCO2H, R:H2O2, 3 h, 100°C
2.1R:H2SO4, R:HNO3, 1.5 h, 100°C

Reference

Influence of the 5-HT6 Receptor on Acetylcholine Release in the Cortex: Pharmacological Characterization of 4-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine, a Potent and Selective 5-HT6 Receptor Antagonist

By Riemer, Claus et al, Journal of Medicinal Chemistry, 1273, 46(7), 1273-1276

Production Method 15

626-05-1

98027-81-7

Reaction Conditions

1.1R:H2O2, S:F3CCO2H, S:H2O
2.1R:HNO3, R:H2SO4 ?SO3

Reference

4,4'-Donor-substituted and 6,6'-difunctionalized 2,2'-bipyridines

By Neumann, Uwe and Voegtle, Fritz, Chemische Berichte, 1989, 122(3), 589-91

Production Method 16

626-05-1

98027-81-7

Reaction Conditions

1.1R:CF3CO3H, R:F3CCO2H, R:H2O2, S:H2O
2.1R:HNO3, R:H2SO4

Reference

New synthesis of 2,6-dibromopyridine N-oxide

By Evans, R. F. et al, Recueil des Travaux Chimiques des Pays-Bas et de la Belgique, 1959, , 408-11

Production Method 17

25373-69-7

98027-81-7

Reaction Conditions

1.1R:HNO3, S:H2SO4

Reference

Derivatives of pyridine N-oxide. XVI. Mercuration of pyridine N-oxide

By van Ammers, M. and den Hertog, H. J., Recueil des Travaux Chimiques des Pays-Bas et de la Belgique, 1958, , 340-5

2,6-Dibromo-4-nitropyridine oxide Raw materials

• 2,6-Dibromopyridine
• 2,6-Dibromopyridine 1-oxide

2,6-Dibromo-4-nitropyridine oxide Preparation Products

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

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Professional Introduction to 2,6-Dibromo-4-nitropyridine oxide (CAS No. 98027-81-7)

2,6-Dibromo-4-nitropyridine oxide is a significant compound in the field of chemical and pharmaceutical research, characterized by its unique molecular structure and versatile reactivity. This compound, identified by the CAS number 98027-81-7, has garnered considerable attention due to its potential applications in the synthesis of advanced materials and pharmaceutical intermediates. The presence of both bromine and nitro substituents on the pyridine ring endows it with distinct chemical properties that make it a valuable building block in organic synthesis.

The molecular structure of 2,6-Dibromo-4-nitropyridine oxide consists of a pyridine core substituted with two bromine atoms at the 2- and 6-positions and a nitro group at the 4-position. This arrangement creates a highly reactive system that can undergo various chemical transformations, including nucleophilic substitution, metal-catalyzed coupling reactions, and oxidation processes. The nitro group, in particular, is known for its ability to participate in reduction reactions to form amines, which are crucial in the synthesis of many biologically active compounds.

In recent years, 2,6-Dibromo-4-nitropyridine oxide has been extensively studied for its role in the development of novel pharmaceuticals. Researchers have leveraged its reactivity to construct complex heterocyclic frameworks that are prevalent in many drug molecules. For instance, studies have demonstrated its utility in the synthesis of kinase inhibitors, which are essential in treating various forms of cancer. The bromine substituents provide handles for further functionalization, allowing chemists to introduce additional groups such as amines or thiols through cross-coupling reactions like Suzuki or Buchwald-Hartwig couplings.

The compound's significance extends beyond pharmaceuticals into the realm of materials science. Its ability to form stable coordination complexes with transition metals has made it a candidate for developing new catalysts and luminescent materials. In particular, the interaction between 2,6-Dibromo-4-nitropyridine oxide and palladium or copper catalysts has been explored for applications in organic light-emitting diodes (OLEDs) and photovoltaic devices. These applications highlight the compound's potential as a precursor for advanced functional materials that could revolutionize display technologies and renewable energy solutions.

Recent advancements in synthetic methodologies have further enhanced the utility of 2,6-Dibromo-4-nitropyridine oxide. Techniques such as flow chemistry and microwave-assisted synthesis have enabled more efficient and scalable production processes. These innovations have not only improved yields but also reduced reaction times, making it more feasible to incorporate this compound into industrial applications. Additionally, green chemistry principles have guided efforts to develop solvent-free or water-based reaction conditions, minimizing environmental impact while maintaining high reaction efficiencies.

The pharmacological potential of derivatives of 2,6-Dibromo-4-nitropyridine oxide continues to be a focal point of research. Studies have shown that modifications to the pyridine ring can significantly alter biological activity. For example, replacing one of the bromine atoms with an alkyl or aryl group can enhance binding affinity to specific targets. Such structural modifications are often guided by computational modeling techniques that predict how changes in the molecular framework will affect biological function. This interdisciplinary approach combines expertise from organic chemistry, medicinal chemistry, and computational science to accelerate the discovery of new therapeutic agents.

The compound's stability under various conditions is another critical factor that contributes to its widespread use. Unlike some reactive intermediates that degrade rapidly upon storage or exposure to light, 2,6-Dibromo-4-nitropyridine oxide maintains its integrity under ambient conditions when handled properly. This stability ensures consistent performance in synthetic protocols and reduces waste by minimizing side reactions caused by decomposition.

In conclusion, 2,6-Dibromo-4-nitropyridine oxide (CAS No. 98027-81-7) represents a cornerstone in modern chemical research with applications spanning pharmaceuticals and advanced materials. Its unique structural features and reactivity make it an indispensable tool for chemists seeking to develop innovative solutions across multiple industries. As research continues to uncover new possibilities for this compound, its importance is likely to grow even further.

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