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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzamides
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Benzamides

Introduction to 2-(N,N-Dimethylaminocarbonyl)phenylboronic acid (CAS No. 874219-16-6) and Its Applications in Modern Chemical Biology

2-(N,N-Dimethylaminocarbonyl)phenylboronic acid, identified by the Chemical Abstracts Service Number (CAS No.) 874219-16-6, is a specialized organoboron compound that has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound belongs to a class of boronic acids, which are widely recognized for their utility in various biochemical applications, including drug discovery, biomaterials, and catalysis. The unique structural features of this molecule, particularly the presence of a N,N-dimethylaminocarbonyl (DMAC) group attached to a phenyl ring, coupled with a boronic acid functionality, make it a versatile intermediate in synthetic chemistry and a potential candidate for developing novel therapeutic agents.

The boronic acid moiety in 2-(N,N-Dimethylaminocarbonyl)phenylboronic acid is known for its ability to form stable complexes with diols and other polyhydroxy compounds through reversible coordination interactions. This property has been exploited in various applications, such as affinity chromatography, where it serves as a ligand for capturing proteins with multiple hydroxyl groups. Additionally, boronic acids are integral components in the design of protease inhibitors and have been extensively studied for their role in targeted drug delivery systems.

In recent years, the pharmaceutical industry has seen a surge in the development of boron-containing compounds due to their enhanced bioavailability and improved pharmacokinetic profiles. The N,N-dimethylaminocarbonyl group in 2-(N,N-Dimethylaminocarbonyl)phenylboronic acid not only contributes to the compound's solubility but also influences its reactivity, making it an attractive building block for medicinal chemists. This section explores the latest advancements in the application of this compound, emphasizing its role in innovative drug development and biomolecular interactions.

One of the most compelling aspects of 2-(N,N-Dimethylaminocarbonyl)phenylboronic acid is its potential as a precursor in the synthesis of advanced materials. Boronate esters derived from this compound have been employed in the creation of cross-linking agents for hydrogels, which are widely used in tissue engineering and regenerative medicine. The ability to modulate gelation properties through pH or temperature responsiveness makes this class of materials highly valuable for biomedical applications.

The compound's reactivity also extends to its utility as a catalyst or co-catalyst in organic transformations. For instance, boronic acids can participate in Suzuki-Miyaura cross-coupling reactions, which are pivotal in constructing complex organic molecules. The presence of the N,N-dimethylaminocarbonyl group enhances electrophilic character, facilitating more efficient coupling reactions under milder conditions. This has opened new avenues for synthesizing biaryl compounds, which are prevalent in many biologically active molecules.

Recent studies have highlighted the role of 2-(N,N-Dimethylaminocarbonyl)phenylboronic acid in modulating enzyme activity through boronate ester formation. This mechanism has been explored particularly in the context of glycosidase inhibition, where boronic acids mimic sugar substrates and interfere with enzymatic turnover. Such inhibitors have shown promise in treating metabolic disorders and infectious diseases. The DMAC group further enhances binding affinity by optimizing steric complementarity with target enzymes.

The synthesis of 2-(N,N-Dimethylaminocarbonyl)phenylboronic acid itself is an intriguing challenge that has driven innovation in synthetic methodologies. Modern approaches often involve multi-step sequences that leverage palladium-catalyzed reactions or transition-metal-mediated cross-coupling processes to construct the desired boronic acid functionality efficiently. Advances in green chemistry have also influenced these synthetic routes, emphasizing sustainability through reduced waste generation and energy consumption.

The compound's stability under various conditions makes it suitable for long-term storage and transport, ensuring consistent quality for industrial applications. Analytical techniques such as nuclear magnetic resonance (NMR) spectroscopy and high-performance liquid chromatography (HPLC) are routinely employed to confirm purity and structural integrity before use in research or production settings.

In conclusion, 2-(N,N-Dimethylaminocarbonyl)phenylboronic acid (CAS No. 874219-16-6) represents a cornerstone molecule in modern chemical biology with far-reaching implications across pharmaceuticals, materials science, and catalysis. Its unique structural attributes enable diverse applications, from drug design to advanced biomaterials, underscoring its importance as a research tool and potential therapeutic agent. As scientific understanding evolves, further exploration into its capabilities will undoubtedly yield groundbreaking discoveries.

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• 623580-91-6(Boronic acid,[1,3-phenylenebis[carbonyl(methylimino)methylene-10,9-anthracenediylmethylene(methylimino)methylene-2,1-phenylene]]bis-)
• 121177-82-0(4-(Methylcarbamoyl)phenylboronic Acid)
• 129112-21-6((2-(Diethylcarbamoyl)phenyl)boronic acid)
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• 874459-82-2(Boronic acid,B-[2-(1-piperidinylcarbonyl)phenyl]-)
• 380430-54-6(2-Aminocarbonylphenylboronic acid)
• 405520-68-5(4-(N,N-Dimethylaminocarbonyl)phenylboronic acid)
• 373384-14-6((3-(Dimethylcarbamoyl)phenyl)boronic acid)
• 103681-98-7(2-(Diisopropylcarbanoyl) phenylboronic acid)