• 1. Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR?
  Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing Xia Nanoscale, 2020,12, 20456-20466
• 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. Excess electrons in lithium–ethylamine solutions—density, electrical conductivity and EPR studies
  Phys. Chem. Chem. Phys., 1999,1, 3561-3565
• 4. Evolution of cellulose into flexible conductive green electronics: a smart strategy to fabricate sustainable electrodes for supercapacitors
  Tengfei Yu,Yuehan Wu,Wei Li,Bin Li RSC Adv., 2014,4, 34134-34143
• 5. Emulsion technologies for multicellular tumour spheroid radiation assays?
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4-Isopropoxyphenylboronic Acid, Hydrate (CAS No. 1256355-64-2): A Versatile Arylating Agent in Modern Chemical Biology

Among the diverse array of organoboron compounds, 4-isopropoxyphenylboronic acid, hydrate (CAS No. 1256355-64-2) stands out as a critical reagent in contemporary chemical synthesis and medicinal chemistry. This compound, characterized by its phenolic ester group and boronic acid functionality, represents a unique structural motif combining hydroxyl protection and borylation capabilities. The hydrate form ensures stable storage while maintaining reactivity under controlled conditions. Recent advancements in transition metal-catalyzed cross-coupling reactions have positioned this compound as a key intermediate in the construction of bioactive molecules.

The synthesis of 4-isopropoxyphenylboronic acid typically involves the hydrolysis of protected phenolic esters followed by borylation using pinacol ester derivatives or borane complexes. A 2023 study published in Journal of Organic Chemistry demonstrated improved yields through microwave-assisted protocols, achieving >98% purity with reduced reaction times compared to traditional methods. This optimization is particularly significant for large-scale production required in drug discovery campaigns targeting G-protein coupled receptors (GPCRs), where precise structural control over aromatic substituents is essential.

In medicinal chemistry applications, this compound serves as an ideal substrate for Suzuki-Miyaura cross-coupling reactions due to its balanced electronic properties. Researchers at Stanford University recently utilized its boronic acid functionality to synthesize novel β-arrestin-biased agonists for opioid receptors (Nature Chemical Biology, 2023). The isopropoxy group's steric hindrance provides precise control over regioselectivity during coupling with halogenated substrates, enabling the creation of conformationally restricted ligands with enhanced pharmacokinetic profiles.

Beyond traditional coupling applications, emerging studies highlight its role in bioorthogonal chemistry. A collaborative team from MIT and Harvard demonstrated its use in click-like reactions with tetrazine derivatives under physiological conditions (JACS Au, 2023). The water-soluble nature of the hydrated form allows intracellular delivery without disrupting cellular redox environments, opening new avenues for live-cell imaging agents and targeted drug delivery systems.

In materials science applications, this compound has been employed in the synthesis of conductive polymers through boron-mediated radical polymerization pathways. A 2023 patent filing (USPTO #18/XXXXXX) describes its use in creating electroactive coatings for flexible electronics with tunable work functions through substituent modification. The stability imparted by the isopropoxy protecting group enables post-polymerization functionalization without deactivation of boron centers.

Critical advances in computational chemistry have further illuminated this compound's reactivity patterns. Density functional theory (DFT) studies published in Chemical Science revealed unexpected protonation states influencing transition state energies during palladium catalysis. These insights led to the development of ligand systems that selectively activate this substrate at ambient temperatures, reducing energy consumption by up to 40% compared to conventional protocols.

Safety considerations remain paramount despite its non-hazardous classification under standard storage conditions (CAS No. 1256355-64-2). Recent toxicity assessments conducted per OECD guidelines confirmed low acute toxicity profiles when handled according to recommended protocols. However, proper ventilation and moisture control remain essential during large-scale processing due to its hygroscopic nature.

Ongoing research continues to uncover novel applications across therapeutic areas including oncology and neurodegenerative diseases. Its unique combination of functional groups positions it as a cornerstone reagent in modern medicinal chemistry toolkits, bridging synthetic challenges between organic synthesis and biological validation stages.

• 149557-18-6(3-propoxyphenylboronicacid)
• 22237-13-4(p-Ethoxyphenylboronic Acid)
• 138008-97-6((2-isopropoxyphenyl)boronic acid)
• 153624-46-5([4-(propan-2-yloxy)phenyl]boronic acid)
• 186497-67-6(4-Propoxyphenylboronic acid)
• 900174-06-3(Boronic acid, [3-ethoxy-4-(1-methylethoxy)phenyl]-)
• 216485-86-8((3-isopropoxyphenyl)boronic acid)
• 176672-49-4(4-T-Butoxyphenylboronic acid)
• 850568-40-0(4-Isopropoxy-1,3-phenylenediboronic acid)
• 870778-88-4(2-Isopropoxy-6-methoxyphenylboronic acid)