Production Method 1

884495-10-7

951677-47-7

Reaction Conditions

1.1 Reagents: Butyllithium ,  Triisopropyl borate Solvents: Toluene ;  -45 - -35 °C; 4 h, -45 - -35 °C; -35 °C → -20 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  -15 - 0 °C

Reference

Method for preparing (fluoro)pyridinylboronic acid

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(2-chloro-5-fluoropyridin-4-yl)boronic acid Raw materials

• 4-bromo-2-chloro-5-fluoro-pyridine

(2-chloro-5-fluoropyridin-4-yl)boronic acid Preparation Products

• (2-chloro-5-fluoropyridin-4-yl)boronic acid (951677-47-7)

• 1. Acenaphthenic hopanoids, a novel series of aromatised
  Teresita Carrillo-Hernández,Philippe Schaeffer,Pierre Albrecht Chem. Commun., 2001, 1976-1977
• 2. An approach to C–N activation: coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with tert-amines via a metal-, oxidant- and halogen-free anodic oxidation??
  M. Sheykhan,S. Khani,S. Shaabanzadeh,M. Joafshan Green Chem., 2017,19, 5940-5948
• 3. An autoreduction method to prepare plasmonic gold-embedded polypeptide micelles for synergistic chemo-photothermal therapy?
  Xingjie Wu,Linzhu Zhou,Yue Su,Chang-Ming Dong J. Mater. Chem. B, 2016,4, 2142-2152
• 4. An apparatus for determining small amounts of alchohol in sour milk and urine
  Analyst, 1964,89, 272-275
• 5. An aptamer-based keypad lock system?
  Yaqing Liu,Jiangtao Ren,Jing Li,Jiyang Liu,Erkang Wang Chem. Commun., 2012,48, 802-804

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Halopyridines Polyhalopyridines
• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Introduction to (2-chloro-5-fluoropyridin-4-yl)boronic Acid (CAS No. 951677-47-7)

(2-chloro-5-fluoropyridin-4-yl)boronic acid is a specialized organoboron compound that has garnered significant attention in the field of pharmaceutical and chemical research due to its versatile applications. This compound, identified by the CAS number 951677-47-7, is a key intermediate in the synthesis of various biologically active molecules. Its unique structural features, comprising a pyridine ring substituted with chloro and fluoro groups, make it a valuable building block for the development of innovative drugs and agrochemicals.

The relevance of this compound is underscored by its role in cross-coupling reactions, particularly the Suzuki-Miyaura coupling, which is a cornerstone of modern synthetic organic chemistry. These reactions enable the formation of carbon-carbon bonds under mild conditions, making them highly suitable for the construction of complex molecular architectures. The boronic acid functionality in (2-chloro-5-fluoropyridin-4-yl)boronic acid facilitates these transformations, thereby enabling the synthesis of a wide array of heterocyclic compounds that exhibit promising pharmacological properties.

In recent years, there has been a surge in research focused on developing novel therapeutic agents targeting various diseases. Among these, cancer and infectious diseases have been particularly well-studied. The pyridine scaffold is a common motif in many bioactive molecules, and modifications such as chloro and fluoro substitutions can significantly influence the biological activity of these compounds. For instance, studies have shown that fluorinated pyridines can enhance metabolic stability and binding affinity to biological targets, making them attractive for drug design.

The< strong> CAS number 951677-47-7 provides a unique identifier for this compound, ensuring consistency and accuracy in scientific literature and industrial applications. This standardized nomenclature system is crucial for researchers who need to reference specific chemical entities in their work. The compound's molecular structure, characterized by a boronic acid group attached to a pyridine ring with chloro and fluoro substituents, allows for further functionalization through various chemical reactions. This flexibility makes it an indispensable tool in medicinal chemistry.

Recent advancements in computational chemistry have further highlighted the importance of (2-chloro-5-fluoropyridin-4-yl)boronic acid. Molecular modeling studies have demonstrated that this compound can interact with biological targets in specific ways, providing insights into its potential therapeutic applications. For example, computational simulations have suggested that it may inhibit enzymes involved in cancer cell proliferation or interfere with bacterial biofilm formation. These findings are particularly exciting as they offer new avenues for drug discovery.

The synthesis of< strong> (2-chloro-5-fluoropyridin-4-yl)boronic acid involves multi-step processes that require careful optimization to ensure high yields and purity. Common synthetic routes include halogenation of pyridine derivatives followed by boronation using appropriate reagents. The choice of reagents and reaction conditions can significantly impact the efficiency of these transformations. Researchers often employ green chemistry principles to minimize waste and improve sustainability, ensuring that the production process aligns with environmental standards.

In addition to its pharmaceutical applications, this compound has shown promise in the development of agrochemicals. Pyridine-based compounds are widely used as intermediates in pesticide formulations due to their ability to interact with biological targets in pests while minimizing toxicity to non-target organisms. The< strong> CAS number 951677-47-7 helps distinguish this specific compound from others in the field, facilitating its use in targeted research and development efforts.

The growing interest in fluorinated heterocycles has led to numerous patents and publications detailing new synthetic methodologies and applications for< strong> (2-chloro-5-fluoropyridin-4-yl)boronic acid. These contributions highlight its importance as a building block for innovative chemical synthesis. As research continues to evolve, it is likely that new uses for this compound will be discovered, further expanding its utility in various scientific disciplines.

In conclusion, (2-chloro-5-fluoropyridin-4-yl)boronic acid (CAS No. 951677-47-7) is a versatile and highly valuable compound with significant implications in pharmaceutical and agrochemical research. Its unique structural features make it an excellent candidate for use in cross-coupling reactions and other synthetic transformations. The ongoing research into its applications underscores its importance as a tool for developing novel bioactive molecules that address critical challenges in medicine and agriculture.

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