• 1. Distribution and ecological risk assessment of typical antibiotics in the surface waters of seven major rivers, China?
  Environ. Sci.: Processes Impacts, 2021,23, 1088-1100
• 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. Evolved polymerases facilitate selection of fully 2′-OMe-modified aptamers?
  Zhixia Liu,Tingjian Chen,Floyd E. Romesberg Chem. Sci., 2017,8, 8179-8182
• 4. Enantiomorphic symmetry breaking in crystallization of molten sodium chlorate?
  Martin R. Ward,Gary W. Copeland,Andrew J. Alexander Chem. Commun., 2010,46, 7634-7636
• 5. Excitable dynamics in the bromate–sulfite–ferrocyanide reaction
  J. Zagora,M. Vosla?,L. Schreiberová,I. Schreiber Phys. Chem. Chem. Phys., 2002,4, 1284-1291

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

3-Bromo-5-(difluoromethoxy)pyridine (CAS No. 342602-27-1): A Versatile Building Block in Modern Chemistry

3-Bromo-5-(difluoromethoxy)pyridine (CAS No. 342602-27-1) is a highly valuable heterocyclic compound that has gained significant attention in pharmaceutical and agrochemical research. This brominated pyridine derivative features a unique combination of difluoromethoxy group and bromine substituent, making it an essential intermediate for various synthetic applications. Its molecular formula C₆H₄BrF₂NO and molecular weight of 224.00 g/mol position it as a crucial building block in modern organic synthesis.

The compound's structural features contribute to its growing popularity in drug discovery programs. The electron-withdrawing difluoromethoxy group at the 5-position and the reactive bromine atom at the 3-position create multiple possibilities for further functionalization. Researchers particularly value 3-bromo-5-(difluoromethoxy)pyridine for its ability to participate in cross-coupling reactions, nucleophilic substitutions, and other transformative chemical processes that are fundamental to developing new active pharmaceutical ingredients (APIs).

Recent trends in medicinal chemistry have shown increased interest in fluorinated pyridine derivatives, with 3-bromo-5-(difluoromethoxy)pyridine being no exception. The incorporation of fluorine atoms into drug molecules often improves their metabolic stability, bioavailability, and binding affinity to biological targets. This explains why many researchers are searching for "difluoromethoxy pyridine synthesis" and "bromopyridine building blocks" in scientific databases and chemical marketplaces.

From a synthetic chemistry perspective, 3-bromo-5-(difluoromethoxy)pyridine serves as a precursor for numerous valuable transformations. The bromine atom readily participates in palladium-catalyzed cross-coupling reactions such as Suzuki, Stille, and Buchwald-Hartwig couplings, enabling the construction of complex molecular architectures. Meanwhile, the difluoromethoxy group remains stable under most reaction conditions, providing a handle for further modifications or serving as a permanent structural feature in the final molecule.

The compound's applications extend beyond pharmaceuticals into materials science and specialty chemicals. Its unique electronic properties make it interesting for developing organic electronic materials, particularly in the design of novel charge-transport materials for OLED applications. The presence of both electron-withdrawing (difluoromethoxy) and potentially electron-donating (after bromine substitution) groups allows for fine-tuning of electronic properties in conjugated systems.

Quality control and analytical characterization of 3-bromo-5-(difluoromethoxy)pyridine typically involve techniques such as HPLC purity analysis, GC-MS, and NMR spectroscopy. The compound generally appears as a white to off-white crystalline powder with high chemical stability when stored under appropriate conditions (typically at 2-8°C in a dry environment). These characteristics make it convenient for handling in laboratory settings and industrial-scale applications alike.

Market demand for 3-bromo-5-(difluoromethoxy)pyridine has been steadily increasing, particularly from contract research organizations (CROs) and pharmaceutical companies engaged in drug discovery. Suppliers often highlight its availability in various quantities, from milligram-scale for research purposes to kilogram-scale for process development. The growing interest in "fluorinated heterocycles for drug discovery" and "pyridine-based pharmaceutical intermediates" in scientific literature reflects this compound's importance in contemporary medicinal chemistry.

Environmental and safety considerations for 3-bromo-5-(difluoromethoxy)pyridine follow standard laboratory chemical handling protocols. While not classified as highly hazardous, proper personal protective equipment (PPE) including gloves and safety glasses should be used when handling this compound. Material safety data sheets (MSDS) provided by suppliers contain detailed information about handling, storage, and disposal procedures that comply with regional chemical safety regulations.

The synthesis of 3-bromo-5-(difluoromethoxy)pyridine typically involves multi-step procedures starting from commercially available pyridine precursors. Key steps often include selective bromination and introduction of the difluoromethoxy functionality through various methods such as nucleophilic substitution or oxidative processes. Recent patent literature reveals ongoing innovation in the preparation of this and related compounds, with particular emphasis on improving yield, purity, and scalability of the synthetic routes.

Looking toward future applications, 3-bromo-5-(difluoromethoxy)pyridine continues to attract attention in emerging areas of chemical research. Its potential use in developing PET imaging agents (where fluorine-18 could be incorporated), agricultural chemicals, and specialty materials demonstrates the versatility of this molecular scaffold. The compound's structural features align well with current trends in fragment-based drug discovery and the design of targeted protein degraders (PROTACs), ensuring its relevance in cutting-edge pharmaceutical research.

For researchers considering 3-bromo-5-(difluoromethoxy)pyridine for their projects, several practical considerations should be noted. The compound's solubility profile (typically soluble in common organic solvents like DCM, THF, and DMF but less so in water) influences reaction design and workup procedures. Additionally, its stability under various conditions should be verified for specific applications, especially when planning reactions involving strong bases, acids, or high temperatures that might affect the difluoromethoxy group.

In conclusion, 3-bromo-5-(difluoromethoxy)pyridine (CAS No. 342602-27-1) represents a strategically important building block in modern synthetic chemistry. Its unique combination of functional groups, reactivity patterns, and potential applications in pharmaceuticals and beyond make it a valuable tool for researchers across multiple disciplines. As the demand for fluorinated heterocyclic compounds continues to grow in medicinal chemistry and materials science, this compound is likely to maintain its position as a key intermediate in innovative chemical research and development.

• 374935-00-9(3-Bromo-5-(3-methoxyphenoxy)pyridine)
• 374934-98-2(3-Bromo-5-(4-methoxyphenoxy)pyridine)
• 28232-63-5(3-Bromo-5-phenoxypyridine)
• 1214377-46-4(3-Bromo-4-(difluoromethoxy)pyridine)
• 1241752-50-0(5-Bromo-3-(difluoromethoxy)-2-methoxypyridine)
• 374935-03-2(3-Bromo-5-(4-fluorophenoxy)pyridine)
• 50720-12-2(3-Bromo-5-methoxypyridine)
• 1020253-25-1(8-Bromo-6-trifluoromethoxyquinoline)
• 1280786-71-1(6-Bromo-8-trifluoromethoxyquinoline)
• 1060815-01-1(3-Bromo-5-(trifluoromethoxy)pyridine)