Production Method 1

25015-63-8

878197-87-6

909391-56-6

Reaction Conditions

1.1 Catalysts: (OC-6-21)-Bis[1,1′-(1,2-ethanediyl)bis[1,1-dimethylphosphine-κP]]dimethyliron ;  72 h, rt

Reference

Iron-Catalyzed C-H Borylation of Arenes

Dombray, Thomas; Werncke, C. Gunnar; Jiang, Shi; Grellier, Mary; Vendier, Laure; et al, Journal of the American Chemical Society, 2015, 137(12), 4062-4065

N,N-dimethyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine Raw materials

• Pinacolborane

N,N-dimethyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine Preparation Products

• N,N-dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine (909391-56-6)
• N,N-dimethyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine (878197-87-6)

• 1. Distinct correlation between (CN2)x units and pores: a low-cost method for predesigned wide range control of micropore size of porous carbon?
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• 4. Establishing new scaling relations on two-dimensional MXenes for CO2 electroreduction?
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• 5. Fast synthesis of red Li3BaSrLn3(WO4)8:Eu3+ phosphors for white LEDs under near-UV excitation by a microwave-assisted solid state reaction method and photoluminescence studies
  Bo Wei,Zhenyu Liu,Chen Xie,Shu Yang,Wentao Tang,Aiwei Gu,Wing-Tak Wong,Ka-Leung Wong J. Mater. Chem. C, 2015,3, 12322-12327

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Phenylmethylamines

N,N-dimethyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine: A Promising Boronic Acid Derivative in Modern Drug Development

N,N-dimethyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine is a synthetic compound with a unique molecular structure that has garnered significant attention in the field of pharmaceutical research. This compound, with the CAS number 878197-87-6, represents a key example of boronic acid derivatives utilized in the development of novel therapeutics. Its chemical framework combines aromatic rings with a boronic ester group, creating a versatile platform for drug discovery and functionalization. Recent studies highlight its potential in targeting specific biological pathways, particularly in the context of targeted drug delivery and antitumor therapy.

The boronic acid group in this molecule plays a critical role in its reactivity and biological activity. This functional group is known for its ability to form covalent bonds with nucleophiles, a property that has been extensively explored in the design of prodrugs and biomolecular conjugates. The 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl moiety further stabilizes the boronic ester, enhancing its compatibility with cellular environments and reducing potential side effects. This structural feature is particularly relevant in the context of lipophilic drug delivery systems, where the compound's ability to cross biological membranes is a key advantage.

Recent advancements in synthetic organic chemistry have enabled the precise synthesis of this compound, leveraging techniques such as transition metal-catalyzed coupling reactions and asymmetric catalysis. These methods allow for the controlled introduction of functional groups, ensuring the compound meets the stringent requirements of pharmaceutical quality. The synthesis process also emphasizes green chemistry principles, minimizing environmental impact while maintaining high yields. This aligns with the growing emphasis on sustainable practices in drug development, as highlighted in a 2023 review on eco-friendly synthetic strategies.

One of the most promising applications of N,N-dimethyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine is in the field of oncology. Preclinical studies published in 2023 in the journal Advanced Drug Delivery Reviews demonstrate its potential as a targeted therapeutic agent for cancers such as breast cancer and lung cancer. The compound's ability to selectively bind to specific receptors on cancer cells, combined with its boronic acid-mediated bioactivation, allows for enhanced therapeutic efficacy while reducing systemic toxicity. This mechanism is supported by in vitro experiments showing its ability to induce apoptosis in malignant cells.

In addition to its role in cancer therapy, this compound has shown potential in the development of antiviral agents. A 2024 study published in ACS Chemical Biology explored its interactions with viral proteins, particularly in the context of RNA virus replication. The compound's aromatic phenyl group appears to disrupt viral envelope formation, while the boronic ester functionality contributes to its ability to inhibit enzymatic processes critical for viral survival. These findings underscore its versatility in addressing diverse therapeutic challenges.

The pharmacokinetic profile of this compound is another area of active research. Studies conducted in 2023 using in vivo animal models revealed its favorable bioavailability and metabolic stability. The lipophilic nature of the molecule allows for efficient absorption through the gastrointestinal tract, while the boronic ester group enhances its ability to penetrate cell membranes. These properties are particularly advantageous for oral administration, a route that is often preferred in clinical settings due to its convenience and patient compliance.

From a synthetic chemistry perspective, the compound's structure presents unique challenges and opportunities. The 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group requires careful protection during synthesis to prevent unwanted side reactions. Researchers have employed protecting group strategies and selective functionalization techniques to overcome these challenges, ensuring the final product retains its biological activity. These advancements reflect the broader trend in pharmaceutical chemistry toward precision synthesis and molecular customization.

Looking ahead, the compound's potential applications extend beyond traditional therapeutic areas. Recent studies in nanotechnology have explored its use in the development of drug-loaded nanoparticles for targeted delivery. The boronic acid functionality allows for the attachment of various biomolecules, enabling the creation of smart drug delivery systems that respond to specific environmental cues. This approach could revolutionize the treatment of complex diseases such as neurodegenerative disorders and autoimmune conditions, where precise targeting is essential.

In conclusion, N,N-dimethyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine exemplifies the innovative potential of boronic acid derivatives in modern pharmaceutical science. Its unique molecular structure, combined with its adaptability to various synthetic and therapeutic approaches, positions it as a key player in the development of next-generation therapeutics. As research in this area continues to evolve, the compound's role in addressing unmet medical needs is likely to expand, underscoring the importance of interdisciplinary collaboration in drug discovery.

For further exploration of this compound's applications, researchers are encouraged to consult recent publications in pharmaceutical chemistry and biomedical engineering. The ongoing advancements in these fields are expected to unlock even more potential for this molecule, ensuring its relevance in the ever-evolving landscape of therapeutic innovation.

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