• 1. Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells?
  Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860
• 2. Establishing the accuracy of position-specific carbon isotope analysis of propane by GC-pyrolysis-GC-IRMS
  ChangjieLiu,PengLiu,XiaofengWang,XiaoqiangLi,JuskeHorita
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Nitrobenzenes

4-Nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile: A Versatile Building Block in Modern Chemistry and Pharmaceuticals

4-Nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (CAS No. 1218791-27-5) is a versatile and highly functionalized compound that has gained significant attention in recent years due to its unique properties and wide-ranging applications in the fields of organic synthesis, medicinal chemistry, and materials science. This compound is characterized by its nitro group and boronic ester functionality, which make it an ideal building block for various chemical transformations.

The nitro group in 4-Nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile imparts strong electron-withdrawing properties to the molecule, making it highly reactive in nucleophilic substitution reactions. This reactivity is particularly useful in the synthesis of complex organic molecules and pharmaceutical intermediates. Additionally, the presence of the boronic ester group allows for efficient cross-coupling reactions with a variety of organic halides and other electrophiles through palladium-catalyzed Suzuki-Miyaura coupling reactions.

Recent studies have highlighted the importance of 4-Nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile in the development of novel therapeutic agents. For instance, a research group at the University of California demonstrated that this compound can be used as a key intermediate in the synthesis of potent anti-cancer drugs. The nitro group can be reduced to an amino group under mild conditions, which can then be further functionalized to introduce various bioactive moieties. This flexibility makes it an attractive candidate for drug discovery and development.

In the realm of materials science, 4-Nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile has shown promise as a precursor for the synthesis of advanced functional materials. Its ability to undergo controlled polymerization reactions has led to the development of new types of polymers with tunable properties. These polymers have potential applications in areas such as electronic devices, sensors, and coatings.

The synthesis of 4-Nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile typically involves a multi-step process that begins with the nitration of 3-bromobenzonitrile followed by a boronate ester formation reaction. The nitration step is crucial for introducing the nitro group into the aromatic ring without affecting other functional groups. The subsequent boronate ester formation is achieved using pinacol borane under mild conditions. This synthetic route has been optimized to yield high purity and yield of the final product.

The physical and chemical properties of 4-Nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile are well-characterized. It is a white crystalline solid with a melting point of approximately 100°C. The compound is soluble in common organic solvents such as dichloromethane (DCM), dimethylformamide (DMF), and tetrahydrofuran (THF). Its stability under various reaction conditions makes it suitable for use in both laboratory-scale experiments and industrial processes.

In terms of safety and handling, 4-Nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile should be stored in a cool and dry place away from strong oxidizing agents. It is recommended to handle this compound under inert atmosphere conditions to prevent degradation or unwanted side reactions. Proper personal protective equipment (PPE) should be worn during handling to ensure safety.

The versatility and reactivity of 4-Nitro-3-(4,4,5,5-tetramethyl-1,3，2-dioxaborolan-2-yl)benzonitrile have made it an indispensable tool in modern chemical research. Its unique combination of functional groups allows for a wide range of chemical transformations that are essential for advancing our understanding of complex molecular systems. As research continues to uncover new applications for this compound in various fields such as drug discovery and materials science, its importance is likely to grow even further.

• 849236-22-2(2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline)
• 1218791-26-4(2-Nitro-5-trifluoromethylphenylboronic Acid Pinacol Ester)
• 428820-95-5(3,5-Dinitrophenylboronic acid, pinacol ester)
• 1288978-82-4(2-(4-fluoro-2-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 190788-59-1(4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane)
• 1256359-10-0(4,4,5,5-Tetramethyl-2-(4-methyl-2-nitrophenyl)-1,3,2-dioxaborolane)
• 833486-94-5(2-Nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline)
• 883715-40-0(2-Methyl-4-nitrophenylboronic Acid, pinacol ester)
• 1218791-28-6(4-Nitro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile)
• 957062-84-9(4,4,5,5-Tetramethyl-2-(2-methyl-5-nitrophenyl)-1,3,2-dioxaborolane)