• 1. o-Nitrobenzyl photoremovable groups with fluorescence uncaging reporting properties
  E. Abou Nakad,F. Bolze,A. Specht Org. Biomol. Chem. 2018 16 6115
• 2. Synthesis and characterisation of push–pull flavin dyes with efficient second harmonic generation (SHG) properties
  Nabeel Mohammed,Alan A. Wiles,Michael Belsley,Sara S. M. Fernandes,Michele Cariello,Vincent M. Rotello,M. Manuela M. Raposo,Graeme Cooke RSC Adv. 2017 7 24462
• 3. Sensitized luminescence in dinuclear lanthanide(iii) complexes of bridging 8-hydroxyquinoline derivatives with different electronic properties
  Hai-Bing Xu,Jia Li,Lin-Xi Shi,Zhong-Ning Chen Dalton Trans. 2011 40 5549
• 4. Synthesis, conformational stability and molecular structure of 4-aryl- and 4,5-diaryl-1,8-bis(dimethylamino)naphthalenes
  Ekaterina A. Filatova,Eugeny A. Ermolenko,Alexander F. Pozharskii,Valery A. Ozeryanskii,Oleg P. Demidov,Anatoly V. Chernyshev,Anatoly V. Metelitsa,Anna V. Gulevskaya Org. Biomol. Chem. 2023 21 3388
• 5. Through space charge-transfer emission in lambda (Λ)-shaped triarylboranes and the use in fluorescent sensing for fluoride and cyanide ions
  He Xi,Yang Liu,Chun-Xue Yuan,Ye-Xin Li,Lei Wang,Xu-Tang Tao,Xiao-Hua Ma,Chun-Fu Zhang,Yue Hao RSC Adv. 2015 5 45668

• Solvents and Organic Chemicals Organic Compounds Organic nitrogen compounds Organonitrogen compounds Amines Tertiary amines
• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Introduction to (4-(dimethylamino)phenyl)boronic Acid (CAS No. 28611-39-4)

(4-(dimethylamino)phenyl)boronic acid, identified by its CAS number 28611-39-4, is a significant compound in the field of chemical biology and pharmaceutical research. This organoboron derivative features a phenyl ring substituted with a dimethylamino group and a boronic acid functional group, making it a versatile intermediate in synthetic chemistry and a promising candidate for various applications in drug development.

The compound's structure imparts unique reactivity, particularly its boronic acid moiety, which is well-known for its role in Suzuki-Miyaura cross-coupling reactions. These reactions are fundamental in constructing biaryl compounds, which are prevalent in many biologically active molecules. The presence of the dimethylamino group enhances the electrophilicity of the boronic acid, facilitating efficient coupling with aryl halides or other boronic acids under palladium catalysis.

In recent years, (4-(dimethylamino)phenyl)boronic acid has garnered attention for its applications in the development of targeted drug delivery systems. Its ability to participate in controlled-release mechanisms has been explored in nanomedicine, where it aids in the synthesis of polymeric nanoparticles designed for specific therapeutic applications. The compound's compatibility with biodegradable polymers has opened new avenues for creating sustained-release formulations, improving the efficacy and reducing the side effects of pharmaceuticals.

Moreover, research has highlighted the potential of (4-(dimethylamino)phenyl)boronic acid in diagnostic imaging and contrast enhancement techniques. Boron-containing compounds have been utilized in magnetic resonance imaging (MRI) due to their ability to interact with magnetic fields, providing enhanced contrast for better visualization of internal structures. The dimethylamino group not only improves solubility but also enhances relaxivity, making this compound an attractive candidate for next-generation MRI contrast agents.

The pharmaceutical industry has also leveraged (4-(dimethylamino)phenyl)boronic acid in the synthesis of kinase inhibitors. Kinases are enzymes that play crucial roles in cell signaling pathways, and their dysregulation is often associated with diseases such as cancer. By incorporating this boronic acid derivative into kinase inhibitors, researchers have developed highly specific drugs that can modulate these pathways effectively. The dimethylamino group contributes to the binding affinity and selectivity of these inhibitors, leading to more potent therapeutic agents.

Recent advancements in computational chemistry have further expanded the utility of (4-(dimethylamino)phenyl)boronic acid. Molecular modeling studies have demonstrated its potential as a ligand in metal-organic frameworks (MOFs), where it can coordinate with transition metals to form stable complexes. These MOFs have applications in catalysis, gas storage, and separation technologies. The boronic acid group provides a unique interaction site for metal coordination, while the dimethylamino moiety enhances steric stability and functionalization possibilities.

Additionally, the compound has been investigated for its role in bioconjugation chemistry. Its boronic acid functionality allows for facile attachment to biomolecules such as peptides and proteins through oxime ligation or click chemistry reactions. This capability is particularly valuable in developing biologics and biosensors, where precise molecular modifications are essential for functionality and specificity.

The environmental impact of using (4-(dimethylamino)phenyl)boronic acid has also been considered. Efforts have been made to optimize synthetic routes to minimize waste and improve atom economy. Green chemistry principles have been applied to develop more sustainable methods for producing this compound, ensuring that its use aligns with global efforts towards environmental responsibility.

In conclusion, (4-(dimethylamino)phenyl)boronic acid (CAS No. 28611-39-4) is a multifaceted compound with broad applications across multiple scientific disciplines. Its unique structural features make it an invaluable tool in pharmaceutical research, diagnostic imaging, nanomedicine, and materials science. As research continues to uncover new possibilities, this compound is poised to play an even greater role in advancing scientific knowledge and technological innovation.

• 178752-79-9((3-(dimethylamino)phenyl)boronic acid)
• 302348-49-8(4-(Methylamino)phenylboronic acid)
• 1256355-23-3(3-Dimethylaminophenylboronic acid, hydrochloride)
• 201802-67-7(4-(Diphenylamino)benzeneboronic acid)
• 877064-60-3(3-(methylamino)phenylboronic acid)
• 503299-18-1(Boronic acid, [6-(diphenylamino)-2-naphthalenyl]-)
• 1150114-73-0([4-(dimethylamino)phenyl]boronic acid;hydrochloride)
• 89291-23-6(2-(Dimethylamino)phenylboronic acid)
• 245737-33-1(TBPA)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)