Production Method 1

626-05-1

5140-72-7

912934-77-1

Reaction Conditions

1.1 Reagents: Butyllithium ,  Dibutylmagnesium Solvents: Tetrahydrofuran ;  -10 °C; 1 h, -10 °C
1.2 Reagents: Sulfuryl chloride Solvents: Toluene ;  10 min, -10 °C

Reference

Efficient and scalable synthesis of pyridine sulfonamides

Emura, Takashi; et al, Synlett, 2011, (8), 1117-1120

2-Bromo-6-chloropyridine Raw materials

• 2,6-Dibromopyridine

2-Bromo-6-chloropyridine Preparation Products

• 6-Bromopyridine-2-sulfonyl chloride (912934-77-1)
• 2-Bromo-6-chloropyridine (5140-72-7)

• 1. Synthesis of 2,6-disubstituted pyridin-3-yl C-2′-deoxyribonucleosides through chemoselective transformations of bromo-chloropyridine C-nucleosides
  Tomá? Kubelka,Lenka Slavětínská,Václav Eigner,Michal Hocek Org. Biomol. Chem. 2013 11 4702
• 2. 296. Nitro-compounds as am?bicides. Part I. Compounds related to 2-di-(2-hydroxyethyl)amino-5-nitropyridine
  A. R. Brown,F. C. Copp,A. R. Elphick J. Chem. Soc. 1957 1544

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

Introduction to 2-Bromo-6-chloropyridine (CAS No. 5140-72-7)

2-Bromo-6-chloropyridine, with the chemical formula C?H?BrClN, is a significant intermediate in the field of pharmaceutical and agrochemical synthesis. This heterocyclic compound features both bromo and chloro substituents on a pyridine ring, making it a versatile building block for various chemical transformations. Its unique structure allows for selective functionalization, enabling the development of novel compounds with potential biological activities.

The compound is widely recognized for its utility in medicinal chemistry due to its ability to participate in nucleophilic substitution reactions, cross-coupling reactions, and other synthetic pathways. The presence of both halogen atoms enhances its reactivity, making it particularly valuable in the construction of more complex molecules. Researchers have leveraged these properties to synthesize a range of derivatives with applications in drug discovery and material science.

In recent years, 2-Bromo-6-chloropyridine has garnered attention for its role in the development of small-molecule inhibitors targeting various diseases. For instance, studies have demonstrated its efficacy in generating compounds that interact with protein kinases, which are key targets in oncology research. The bromo and chloro groups provide handles for further derivatization, allowing chemists to fine-tune the pharmacophore and optimize potency and selectivity.

One notable application of 2-Bromo-6-chloropyridine is in the synthesis of kinase inhibitors used in cancer therapy. By employing palladium-catalyzed cross-coupling reactions, researchers can introduce aryl or heteroaryl groups into the pyridine core, creating molecules with enhanced binding affinity to target enzymes. These modifications have led to the discovery of several lead compounds that are currently undergoing preclinical evaluation.

Additionally, 2-Bromo-6-chloropyridine has been utilized in the development of agrochemicals, where it serves as a precursor for herbicides and fungicides. Its structural features allow for the creation of compounds that disrupt essential metabolic pathways in pests while maintaining low toxicity to crops. This has opened up new avenues for sustainable agriculture by providing farmers with effective tools to protect their yields.

The compound's reactivity also makes it a valuable tool in organic synthesis research. Transition-metal catalysts such as palladium and copper can be employed to facilitate diverse transformations, including Suzuki-Miyaura coupling, Buchwald-Hartwig amination, and Heck reactions. These methodologies enable the construction of complex molecular architectures, which are essential for designing advanced materials and functional dyes.

Recent advances in flow chemistry have further expanded the applications of 2-Bromo-6-chloropyridine. Continuous-flow systems allow for precise control over reaction conditions, improving yield and scalability while minimizing waste. This approach has been particularly beneficial in synthesizing libraries of compounds for high-throughput screening, accelerating the discovery process in drug development.

The versatility of 2-Bromo-6-chloropyridine extends to its use in material science. Researchers have explored its incorporation into organic semiconductors and light-emitting diodes (OLEDs), where its electron-withdrawing properties contribute to improved device performance. By tailoring the substituents on the pyridine ring, scientists can modulate electronic characteristics, paving the way for next-generation electronic devices.

In conclusion, 2-Bromo-6-chloropyridine (CAS No. 5140-72-7) is a multifaceted compound with broad applications across pharmaceuticals, agrochemicals, and materials science. Its unique structural features enable diverse synthetic strategies, making it an indispensable tool for chemists and researchers worldwide. As new methodologies emerge and our understanding of molecular interactions deepens, the importance of this compound is likely to grow even further.

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