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

Introduction to 3,5-Difluoropyridine-4-boronic acid pinacol ester (CAS No. 1310404-59-1)

3,5-Difluoropyridine-4-boronic acid pinacol ester, identified by the Chemical Abstracts Service Number (CAS No.) 1310404-59-1, is a significant intermediate in modern synthetic chemistry and pharmaceutical research. This compound belongs to the class of boronic acid esters, which are widely recognized for their utility in cross-coupling reactions, particularly the Suzuki-Miyaura coupling. The presence of both fluorine substituents at the 3- and 5-positions of the pyridine ring imparts unique electronic and steric properties, making it a valuable building block for the development of novel agrochemicals, pharmaceuticals, and materials.

The 3,5-Difluoropyridine-4-boronic acid pinacol ester is synthesized through carefully controlled reactions that ensure high purity and yield. The boronic acid pinacol ester moiety enhances the stability of the boronate group, facilitating its use in various organic transformations. This stability is crucial for applications in pharmaceutical synthesis, where side reactions can compromise the integrity of the final product.

In recent years, there has been growing interest in fluorinated heterocycles due to their enhanced bioavailability, metabolic stability, and binding affinity towards biological targets. The 3,5-Difluoropyridine-4-boronic acid pinacol ester leverages these advantages by serving as a key precursor in the synthesis of fluorinated pyridine derivatives. These derivatives have shown promise in various therapeutic areas, including oncology, antiviral therapy, and central nervous system disorders.

One of the most notable applications of 3,5-Difluoropyridine-4-boronic acid pinacol ester is in the development of small-molecule inhibitors targeting protein-protein interactions. Fluorinated pyridines can modulate the electronic properties of drug candidates, leading to improved binding kinetics and selectivity. For instance, recent studies have demonstrated its role in synthesizing inhibitors for kinases and other enzymes involved in cancer pathways. The Suzuki-Miyaura cross-coupling reaction, facilitated by this compound, allows for the introduction of complex aryl groups into pyridine scaffolds, expanding the structural diversity of potential drug candidates.

The pharmaceutical industry has also explored 3,5-Difluoropyridine-4-boronic acid pinacol ester for its potential in creating novel antiviral agents. Fluorinated pyridines exhibit unique interactions with viral proteases and polymerases, making them effective at inhibiting viral replication. Researchers have utilized this compound to develop inhibitors against viruses such as HIV and hepatitis C. The boronic acid ester functionality ensures that these inhibitors can be efficiently synthesized and modified for optimal pharmacological activity.

Beyond pharmaceuticals, 3,5-Difluoropyridine-4-boronic acid pinacol ester finds applications in materials science and agrochemicals. Its ability to participate in cross-coupling reactions makes it a valuable tool for constructing complex organic molecules used in liquid crystals, organic electronics, and advanced polymers. In agrochemicals, fluorinated pyridines contribute to the development of pesticides with improved efficacy and environmental compatibility.

The synthesis of 3,5-Difluoropyridine-4-boronic acid pinacol ester typically involves halogenation followed by lithiation or metalation at the desired positions on the pyridine ring. Subsequent reaction with a boronate precursor yields the desired product. Advances in synthetic methodologies have improved the efficiency and scalability of these processes, making CAS No. 1310404-59-1 more accessible for industrial applications.

Recent research has also highlighted the importance of fluorinated pyridines in medicinal chemistry due to their ability to enhance drug-like properties such as lipophilicity and solubility. The 3-position fluoro substituent, in particular, has been shown to improve metabolic stability by preventing oxidative degradation. Similarly, the 5-position fluoro group can modulate electronic effects across adjacent functional groups, influencing overall pharmacokinetics.

The utility of 3,5-Difluoropyridine-4-boronic acid pinacol ester extends to fragment-based drug design strategies. By providing a versatile scaffold for synthesizing diverse libraries of compounds, this intermediate enables high-throughput screening programs aimed at identifying novel therapeutic agents. Its compatibility with automated synthesis platforms further enhances its appeal for medicinal chemists seeking efficient ways to explore chemical space.

In conclusion,3,5-Difluoropyridine-4-boronic acid pinacol ester (CAS No. 1310404-59-1) is a multifunctional compound with broad applications across synthetic chemistry, pharmaceutical research, agrochemical development, and materials science. Its unique structural features make it an indispensable tool for constructing complex molecules with tailored properties, contributing significantly to advancements in drug discovery and material innovation.

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• 1622217-35-9(2,5-Difluoropyridine-4-boronic acid, pinacol estser)
• 1072009-08-5(5-fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole)
• 1207623-96-8(6-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole)
• 1220219-91-9(4-fluoro-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine)
• 1029654-43-0(2-Chloro-3-fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine)
• 719268-92-5(3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine)
• 852062-12-5(Quinoline, 3-fluoro-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-)
• 1269440-73-4(2-Pyridinamine, 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-)
• 1256360-62-9(2-Chloro-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine)