Production Method 1

617-86-7

73183-34-3

365564-09-6

797762-23-3

Reaction Conditions

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Solvents: Tetrahydrofuran ;  16 h, 80 °C
2.1 Catalysts: (SP-5-23)-[3,8-Bis[3,5-bis(trifluoromethyl)phenyl]-1,10-phenanthroline-κN1,κN10]… Solvents: Methylcyclohexane ;  20 min, 100 °C

Reference

Iridium-Catalyzed Borylation of Primary Benzylic C-H Bonds without a Directing Group: Scope, Mechanism, and Origins of Selectivity

Larsen, Matthew A.; et al, Journal of the American Chemical Society, 2015, 137(26), 8633-8643

Production Method 2

745783-97-5

100-84-5

365564-09-6

797762-23-3

Reaction Conditions

1.1 Catalysts: (SP-5-23)-[3,8-Bis[3,5-bis(trifluoromethyl)phenyl]-1,10-phenanthroline-κN1,κN10]… Solvents: Methylcyclohexane ;  20 min, 100 °C

Reference

Iridium-Catalyzed Borylation of Primary Benzylic C-H Bonds without a Directing Group: Scope, Mechanism, and Origins of Selectivity

Larsen, Matthew A.; et al, Journal of the American Chemical Society, 2015, 137(26), 8633-8643

1,3,2-Dioxaborolane, 2-(3-methoxy-5-methylphenyl)-4,4,5,5-tetramethyl- Raw materials

• Triethylsilane
• Et3SiB(pinacolato)
• Bis(pinacolato)diborane
• Meta-Methylanisole

1,3,2-Dioxaborolane, 2-(3-methoxy-5-methylphenyl)-4,4,5,5-tetramethyl- Preparation Products

• 1,3,2-Dioxaborolane, 2-(3-methoxy-5-methylphenyl)-4,4,5,5-tetramethyl- (365564-09-6)
• 2-(3-Methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (797762-23-3)

• 1. Enantiocontrolled construction of sistodiolynne, an unusual polyketide from the wood-decay fungus Sistrema raduloides
  Chem. Commun., 1997, 767-768
• 2. Examination of the hydrogen-bonding networks in small water clusters (n = 2–5, 13, 17) using absolutely localized molecular orbital energy decomposition analysis?
  Erika A. Cobar,Paul R. Horn,Robert G. Bergman,Martin Head-Gordon Phys. Chem. Chem. Phys., 2012,14, 15328-15339
• 3. Excited state potential energy surfaces and their interactions in FeIVO active sites
  Shaun D. Wong,Edward I. Solomon Dalton Trans., 2014,43, 17567-17577
• 4. 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
• 5. Estimation of activation energy for electroporation and pore growth rate in liquid crystalline and gel phases of lipid bilayers using molecular dynamics simulations?
  Amit Kumar Majhi,Subbarao Kanchi,V. Venkataraman,K. G. Ayappa,Prabal K. Maiti Soft Matter, 2015,11, 8632-8640

1,3,2-Dioxaborolane, 2-(3-methoxy-5-methylphenyl)-4,4,5,5-tetramethyl-: A Versatile Synthetic Intermediate in Modern Medicinal Chemistry

1,3,2-Dioxaborolane, 2-(3-methoxy-5-methylphenyl)-4,4,5,5-tetramethyl- is a pivotal compound in the field of medicinal chemistry, characterized by its unique 1,3,2-dioxaborolane core and functionalized aromatic substituents. This compound, with the CAS number 365564-09-6, represents a critical building block for the synthesis of diverse pharmaceutical agents. Recent advancements in catalytic methodologies have significantly enhanced its utility in asymmetric synthesis and drug development, making it a focal point of contemporary research.

The 1,3,2-dioxaborolane framework is particularly noteworthy for its ability to participate in various coupling reactions, such as Suzuki-Miyaura and Stille cross-coupling, which are widely employed in the construction of complex organic molecules. The presence of the 4,4,5,5-tetramethyl groups in the molecule provides steric bulk, which can influence the reactivity and selectivity of these reactions. This structural feature is crucial for the design of bioactive molecules with improved pharmacokinetic profiles.

Recent studies have highlighted the role of 1,3,2-dioxaborolane, 2-(3-methoxy-5-methylphenyl)-4,4,5,5-tetramethyl- in the synthesis of aryl ether derivatives with potential therapeutic applications. For instance, a 2023 publication in Journal of Medicinal Chemistry demonstrated its use in the preparation of novel anti-inflammatory agents targeting the NF-κB signaling pathway. The 3-methoxy-5-methylphenyl substituent was found to modulate the interaction of the final product with cellular receptors, enhancing its bioavailability and reducing off-target effects.

The 1,3,2-dioxaborolane core also serves as a versatile platform for the development of prodrugs. Researchers at the University of Tokyo recently reported the use of this compound in the synthesis of a prodrug for the treatment of neurodegenerative diseases. The 4,4,5,5-tetramethyl groups were shown to protect the active moiety from premature degradation, ensuring targeted release in the central nervous system. This approach has opened new avenues for the design of site-specific therapeutic agents.

Advancements in asymmetric catalysis have further expanded the applications of 1,3,2-dioxaborolane, 2-(3-methoxy-5-methylphenyl)-4,4,5,5-tetramethyl-. A 2024 study published in Angewandte Chemie described the use of chiral phosphoric acid catalysts to achieve high enantioselectivity in the coupling reactions involving this compound. The resulting enantiomers exhibited significantly different biological activities, underscoring the importance of stereochemistry in drug development. This finding has implications for the design of more effective and safer pharmaceuticals.

The 3-methoxy-5-methylphenyl substituent in the molecule is also of interest due to its potential to modulate protein-ligand interactions. A 2023 study in ACS Medicinal Chemistry Letters explored its role in the development of kinase inhibitors. The methoxy group was found to enhance the binding affinity of the final compound to the target kinase, while the methyl group contributed to the stability of the protein-ligand complex. These findings highlight the significance of functional group optimization in drug discovery.

Furthermore, the 1,3,2-dioxaborolane core has been utilized in the synthesis of biodegradable polymers for drug delivery applications. A collaborative effort between researchers at MIT and Harvard University demonstrated its use in the creation of stimuli-responsive hydrogels. These hydrogels, which incorporate the 4,4,5,5-tetramethyl groups, exhibit controlled release of therapeutic agents in response to specific environmental cues, such as pH or temperature changes. This innovation has potential applications in targeted drug delivery and regenerative medicine.

The synthesis of 1,3,2-dioxaborolane, 2-(3-methoxy-5-methylphenyl)-4,4,5,5-tetramethyl- has also been optimized through green chemistry approaches. A 2024 review in Green Chemistry discussed the use of catalytic systems to reduce the environmental impact of its production. The adoption of atom-efficient methodologies has not only improved the sustainability of its synthesis but also lowered the cost of large-scale production, making it more accessible for pharmaceutical applications.

In addition to its synthetic utility, the 1,3,2-dioxaborolane core has shown promise in the development of imaging agents for in vivo diagnostics. Researchers at the Max Planck Institute recently reported the use of this compound in the creation of fluorescent probes. The 4,4,5,5-tetramethyl groups were found to enhance the fluorescence quantum yield, allowing for high-resolution imaging of specific cellular targets. This application has the potential to revolutionize the field of molecular imaging and enable real-time monitoring of therapeutic interventions.

The 3-methoxy-5-methylphenyl substituent also plays a role in the modulation of metabolic pathways. A 2023 study in Journal of Biological Chemistry investigated its impact on the activity of certain metabolic enzymes. The results indicated that the presence of this substituent could alter the enzyme's substrate specificity, offering new possibilities for the design of metabolic modulators. This finding has implications for the treatment of metabolic disorders and the development of personalized medicine.

Overall, the versatility of 1,3,2-dioxaborolane, 2-(3-methoxy-5-methylphenyl)-4,4,5,5-tetramethyl- in synthetic chemistry and its potential applications in drug development underscore its importance in modern pharmaceutical research. Continued exploration of its reactivity and functional group modifications is expected to yield further innovations in the field of medicinal chemistry.

As the field of catalytic chemistry continues to evolve, the role of 1,3,2-dioxaborolane, 2-(3-methoxy-5-methylphenyl)-4,4,5,5-tetramethyl- in the synthesis of complex molecules is likely to expand. The integration of advanced computational methods with experimental studies will further enhance our understanding of its reactivity and enable the design of more efficient synthetic strategies. This ongoing research is poised to contribute to the development of next-generation pharmaceuticals with improved efficacy and safety profiles.

Moreover, the environmental benefits of sustainable synthesis methods involving this compound are expected to gain increasing attention. As the pharmaceutical industry seeks to reduce its carbon footprint, the adoption of green chemistry principles in the production of 1,3,2-dioxaborolane, 2-(3-methoxy-5-methylphenyl)-4,4,5,5-tetramethyl- will play a crucial role in achieving long-term sustainability goals. This shift towards eco-friendly practices is likely to influence the broader landscape of drug development and manufacturing.

In conclusion, the 1,3,2-dioxaborolane, 2-(3-methoxy-5-methylphenyl)-4,4,5,5-tetramethyl- molecule represents a significant advancement in synthetic chemistry and pharmaceutical science. Its unique structural features and reactivity have enabled the development of novel therapeutics, imaging agents, and sustainable manufacturing processes. As research in this area continues to progress, the molecule is expected to remain a cornerstone in the quest for innovative solutions in medicine and materials science.

• 1326662-69-4(2-Methoxy-4-Methylphenylboronic Acid Pinacol Ester)
• 1218789-80-0(3-(Cyclopropylmethoxy)-5-methylphenylboronic acid, pinacol ester)
• 1218789-71-9(3-Ethoxy-5-methylphenylboronic acid, pinacol ester)
• 1218789-78-6(3-Isobutoxy-5-methylphenylboronic acid, pinacol ester)
• 889659-70-5(3-Hydroxy-5-methylphenylboronic acid, pinacol ester)
• 1035266-33-1(3-Methoxy-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile)
• 1218790-19-2(3,4-Dimethyl-5-methoxyphenylboronic acid, pinacol ester)
• 1218789-75-3(3-Isopropoxy-5-methylphenylboronic acid, pinacol ester)
• 1218789-73-1(3-Methyl-5-propoxyphenylboronic Acid Pinacol Ester)
• 1218789-82-2(3-Butoxy-5-methylphenylboronic acid, pinacol ester)