Production Method 1

52092-43-0

89488-29-9

Reaction Conditions

1.1 Reagents: Sodium Solvents: Methanol ;  rt; rt → 0 °C
1.2 0 °C → rt; 1 h, rt
1.3 Reagents: Phosphorus tribromide Solvents: Chloroform ;  0 °C; 12 h, reflux; reflux → -18 °C
1.4 Reagents: Sodium hydroxide Solvents: Water ;  basified

Reference

Photocatalytic CO2 Reduction by Trigonal-Bipyramidal Cobalt(II) Polypyridyl Complexes: The Nature of Cobalt(I) and Cobalt(0) Complexes upon Their Reactions with CO2, CO, or Proton

Shimoda, Tomoe; Morishima, Takeshi; Kodama, Koichi ; Hirose, Takuji; Polyansky, Dmitry E.; et al, Inorganic Chemistry, 2018, 57(9), 5486-5498

Production Method 2

96245-98-6

89488-29-9

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran

Reference

Synthetic approaches towards the marine natural products typified by variolin B. A novel fused pyrimidino-7-azaindole

Meigh, Jon-Paul K., 2000, , ,

Production Method 3

620-08-6

89488-29-9

Reaction Conditions

1.1 Reagents: 2-(Dimethylamino)ethanol ,  Butyllithium Solvents: Hexane ;  30 min, -20 °C
1.2 rt; 1 h, rt → -78 °C
1.3 Reagents: 1,2-Dibromo-1,1,2,2-tetrachloroethane Solvents: Tetrahydrofuran ;  rt; overnight, rt
1.4 Reagents: Water ;  0 °C

Reference

Preparation of substituted alkoxypyridines via directed metalation and metal-halogen exchange

Bori, Ibrahim D.; Comins, Daniel L., ARKIVOC (Gainesville, 2021, (5), 57-72

Production Method 4

36953-40-9

89488-29-9

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  30 min, rt; rt → 0 °C
1.2 Solvents: Dimethylformamide ;  0 °C; 0 °C → rt; 3 d, rt
1.3 Reagents: Water ;  rt

Reference

4,4''-Disubstituted Terpyridines and Their Homoleptic FeII Complexes

Harzmann, Gero D.; Neuburger, Markus; Mayor, Marcel, European Journal of Inorganic Chemistry, 2013, 2013(19), 3334-3347

Production Method 5

117873-72-0

89488-29-9

Reaction Conditions

1.1 Reagents: Chloro(1-methylethyl)magnesium Solvents: Tetrahydrofuran ,  Hexane ;  0 °C; 2 h, 0 °C
1.2 Reagents: Methanol-d4 Solvents: Methanol ;  1 min, 0 °C; 1 h, 25 °C
1.3 Reagents: Ammonium chloride Solvents: Water

Reference

Palladium-Catalyzed Hydrocarbonylative Cyclization Enabled by Formal Insertion of Aromatic C=N Bonds into Pd-Acyl Bonds

Zhou, Xibing; Chen, Anrong; Du, Wei; Wang, Yawen; Peng, Yu ; et al, Organic Letters, 2019, 21(22), 9114-9118

2-bromo-4-methoxy-pyridine Raw materials

• 2,6-Dibromo-4-methoxypyridine
• 2,3-dibromo-4-methoxypyridine
• 2-bromo-4-nitro-1-oxido-pyridin-1-ium
• 2-Bromopyridin-4-ol
• 4-Methoxypyridine

2-bromo-4-methoxy-pyridine Preparation Products

• 2-bromo-4-methoxy-pyridine (89488-29-9)

• 1. 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
• 2. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788
• 3. Exchanged ligands on the surface of a giant cluster: [(MoO3)176(H2O)63(CH3OH)17Hn](32 – n)–
  Chem. Commun., 1998, 1501-1502
• 4. Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries?
  Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde Wang J. Mater. Chem. A, 2018,6, 516-526
• 5. Empowering microfluidics by micro-3D printing and solution-based mineral coating?
  Hongxia Li,Aikifa Raza,Qiaoyu Ge,Jin-You Lu,TieJun Zhang Soft Matter, 2020,16, 6841-6849

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Alkyl aryl ethers
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ethers Alkyl aryl ethers
• Solvents and Organic Chemicals Organic Compounds

Introduction to 2-bromo-4-methoxy-pyridine (CAS No. 89488-29-9)

2-bromo-4-methoxy-pyridine, with the chemical formula C?H?BrN?O, is a versatile heterocyclic compound that has garnered significant attention in the field of pharmaceutical and chemical research. This compound belongs to the pyridine family, characterized by a nitrogen-containing aromatic ring, and is distinguished by the presence of a bromine substituent at the 2-position and a methoxy group at the 4-position. The unique structural features of 2-bromo-4-methoxy-pyridine make it a valuable intermediate in the synthesis of various biologically active molecules, particularly in drug discovery and development.

The significance of 2-bromo-4-methoxy-pyridine in modern chemistry cannot be overstated. Its molecular structure allows for facile functionalization, making it a preferred building block for constructing more complex pharmacophores. In recent years, this compound has been extensively utilized in the synthesis of small-molecule inhibitors targeting various therapeutic areas, including oncology, neurology, and infectious diseases. The bromine atom at the 2-position serves as a reactive handle for further chemical modifications, such as Suzuki-Miyaura cross-coupling reactions, which are pivotal in constructing biaryl structures found in many drugs.

One of the most compelling applications of 2-bromo-4-methoxy-pyridine is in the development of kinase inhibitors. Kinases are enzymes that play crucial roles in cell signaling pathways, and their dysregulation is often associated with cancer and inflammatory diseases. Researchers have leveraged the reactivity of 2-bromo-4-methoxy-pyridine to design novel inhibitors that selectively target specific kinases. For instance, studies have demonstrated its utility in generating inhibitors of Janus kinases (JAKs), which are implicated in autoimmune disorders like rheumatoid arthritis. The methoxy group at the 4-position enhances solubility and metabolic stability, contributing to the pharmacokinetic profile of these inhibitors.

Another notable area where 2-bromo-4-methoxy-pyridine has made an impact is in the synthesis of antiviral agents. The growing threat of viral infections has spurred research into developing new antiviral drugs with improved efficacy and reduced side effects. Pyridine derivatives, including 2-bromo-4-methoxy-pyridine, have been explored as scaffolds for antiviral compounds due to their ability to interact with viral enzymes and proteins. Recent studies have highlighted its role in developing inhibitors against viral proteases and polymerases, which are essential for viral replication. The bromine substituent facilitates further derivatization, enabling researchers to fine-tune binding interactions with target viral proteins.

The pharmaceutical industry has also recognized the potential of 2-bromo-4-methoxy-pyridine in central nervous system (CNS) drug development. Neurodegenerative diseases such as Alzheimer's and Parkinson's disease are major health challenges, and there is an urgent need for innovative therapeutic strategies. Pyridine-based compounds have shown promise as neuroprotective agents due to their ability to modulate neurotransmitter systems. Researchers have utilized 2-bromo-4-methoxy-pyridine to synthesize novel ligands that interact with receptors involved in neuroprotection and inflammation. These efforts have led to the identification of compounds with potential therapeutic benefits in preclinical studies.

In addition to its pharmaceutical applications, 2-bromo-4-methoxy-pyridine has found utility in agrochemical research. The agrochemical industry continually seeks novel compounds that enhance crop protection while minimizing environmental impact. Pyridine derivatives are known for their biological activity against pests and pathogens, making them valuable candidates for developing new pesticides. Studies have demonstrated that derivatives of 2-bromo-4-methoxy-pyridine exhibit potent insecticidal properties by interfering with insect nervous systems. The structural flexibility of this compound allows for modifications that optimize efficacy while reducing toxicity to non-target organisms.

The synthetic chemistry community has also embraced 2-bromo-4-methoxy-pyridine as a key intermediate in organic synthesis. Its reactivity makes it an ideal candidate for exploring new synthetic methodologies and developing novel synthetic routes to complex molecules. Transition-metal-catalyzed reactions, such as palladium-catalyzed coupling reactions, have been particularly useful in incorporating 2-bromo-4-methoxy-pyridine into larger molecular frameworks. These reactions enable the construction of diverse heterocyclic structures, which are prevalent in many biologically active compounds.

Recent advances in computational chemistry have further enhanced the utility of 2-bromo-4-methoxy-pyridine in drug discovery. Molecular modeling techniques allow researchers to predict how this compound interacts with biological targets at the atomic level. By integrating experimental data with computational simulations, scientists can optimize the structure of 2-bromo-4-methoxy-pyridine derivatives to improve their binding affinity and selectivity. This interdisciplinary approach has accelerated the discovery process and led to the identification of lead compounds with high potential for further development.

The environmental impact of chemical synthesis is another area where 2-bromo-4-methoxy-pyridine has been scrutinized. Green chemistry principles emphasize the development of sustainable synthetic methods that minimize waste and hazardous byproducts. Researchers have explored alternative synthetic routes to 2-bromo-4-methoxy-pyridine that employ environmentally benign reagents and conditions. These efforts align with global initiatives to promote sustainable chemistry practices and reduce the ecological footprint of pharmaceutical manufacturing.

In conclusion, 2-bromo-4-methoxy-pyridine (CAS No. 89488-29-9) is a multifaceted compound with broad applications across pharmaceuticals, agrochemicals, and synthetic chemistry. Its unique structural features make it a valuable intermediate for constructing biologically active molecules, particularly kinase inhibitors, antiviral agents, and CNS drugs. As research continues to uncover new therapeutic targets and synthetic methodologies, 2-bromo-4-methoxy-pyridine will undoubtedly remain a cornerstone compound in modern chemical research.

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