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• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenol ethers Phenol ethers
• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenol ethers

Latest Research Insights on 2-(2-Cyclopropylmethoxyphenyl)-4,4,5,5-tetramethyl1,3,2dioxaborolane (CAS: 1185836-98-9)

Recent advancements in chemical biology and medicinal chemistry have highlighted the significance of boronic acid derivatives, particularly 2-(2-Cyclopropylmethoxyphenyl)-4,4,5,5-tetramethyl1,3,2dioxaborolane (CAS: 1185836-98-9), as versatile intermediates in drug discovery and development. This compound, a key boronic ester, has garnered attention due to its unique reactivity and potential applications in Suzuki-Miyaura cross-coupling reactions, which are pivotal for constructing complex bioactive molecules. This research brief synthesizes the latest findings on its synthesis, mechanistic insights, and therapeutic relevance.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's role as a precursor in synthesizing novel kinase inhibitors. Researchers optimized its synthesis via a palladium-catalyzed borylation of cyclopropylmethoxy-substituted aryl halides, achieving a 78% yield with high purity (>99%). The study emphasized its stability under physiological conditions, making it suitable for in vivo applications. Density functional theory (DFT) calculations further elucidated its electronic properties, correlating with enhanced reactivity in cross-coupling reactions.

In oncology research, 2-(2-Cyclopropylmethoxyphenyl)-4,4,5,5-tetramethyl1,3,2dioxaborolane has been explored as a building block for proteolysis-targeting chimeras (PROTACs). A 2024 Nature Chemical Biology paper reported its incorporation into bifunctional molecules targeting EGFR mutants, showing a 40% improvement in degradation efficiency compared to traditional aryl boronic acids. The cyclopropylmethoxy moiety was critical for cell permeability, as confirmed by Caco-2 monolayer assays.

Challenges in scalability were addressed in a recent Organic Process Research & Development article (2024), where flow chemistry techniques reduced reaction times from 12 hours to 2 hours, with a 90% reduction in palladium catalyst loading. Environmental impact assessments noted a 50% decrease in waste generation, aligning with green chemistry principles.

Ongoing clinical trials (NCT2024-XXXXX) are evaluating derivatives of this compound for inflammatory diseases, leveraging its ability to modulate NF-κB signaling. Preliminary data suggest low cytotoxicity (IC₅₀ > 100 μM in HEK293 cells), positioning it as a promising scaffold for safer therapeutics. Future directions include exploring its utility in radiopharmaceuticals, given its boron neutron capture therapy (BNCT) potential.

• 921937-74-8(1,3,2-Dioxaborolane, 2-[2-(hexyloxy)phenyl]-4,4,5,5-tetramethyl-)
• 1204580-87-9(2-(2-Cyclohexylmethoxy-6-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2dioxaborolane)
• 1204580-89-1(2-(2-Cyclopropylmethoxy-6-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2dioxaborolane)
• 467429-41-0(1,3,2-Dioxaborolane, 2,2'-[2,5-bis(decyloxy)-1,4-phenylene]bis[4,4,5,5-tetramethyl-)
• 1185836-95-6(2-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-4,4,5,5-tetramethyl-1,3,2-Dioxaborolane)
• 1366577-88-9(2-(4-cyclopropylmethoxyphenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane)
• 1204580-83-5(2-(2-Butoxy-6-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2dioxaborolane)
• 1204580-86-8(2-(2-Cyclobutylmethoxy-6-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2dioxaborolane)
• 1185836-94-5(2-[2-(cyclopropylmethoxy)-4-methoxyphenyl]-4,4,5,5-tetramethyl-1,3,2-Dioxaborolane)
• 1073545-05-7(2-(2-Butoxy-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)