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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazines Pyrimidines and pyrimidine derivatives

Comprehensive Overview of 2-Cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (CAS No. 1402166-11-3)

2-Cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (CAS No. 1402166-11-3) is a highly specialized boron-containing heterocyclic compound that has garnered significant attention in pharmaceutical and materials science research. This compound features a pyrimidine core substituted with a cyclohexyl group and a dioxaborolane moiety, making it a versatile intermediate for Suzuki-Miyaura cross-coupling reactions. Its unique structure and reactivity profile have positioned it as a valuable building block in drug discovery and advanced material synthesis.

The growing interest in boron-based compounds like 2-cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine stems from their pivotal role in modern medicinal chemistry. Researchers frequently search for "boronic ester applications" and "pyrimidine derivatives in drug design," reflecting the compound's relevance in developing kinase inhibitors and anticancer agents. The dioxaborolane group enhances stability while maintaining reactivity, addressing common challenges in organoboron chemistry.

From a synthetic perspective, this compound exemplifies the convergence of heterocyclic chemistry and transition metal catalysis. Its CAS No. 1402166-11-3 serves as a critical identifier for researchers investigating "high-yield borylation methods" or "air-stable boronic acid equivalents." The tetramethyl-1,3,2-dioxaborolane unit provides superior handling characteristics compared to free boronic acids, making it ideal for automated synthesis platforms increasingly adopted in high-throughput screening environments.

Material scientists have explored 2-cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine for developing organic electronic materials, particularly in OLED and OFET applications. The compound's ability to participate in polymerization reactions while maintaining conjugated systems aligns with current trends toward "flexible electronics" and "energy-efficient displays." These applications leverage the electron-deficient pyrimidine ring's charge transport properties when incorporated into π-conjugated backbones.

Analytical characterization of this compound typically involves advanced techniques such as NMR spectroscopy (particularly 11B NMR), mass spectrometry, and X-ray crystallography. The boron atom's quadrupolar nature presents unique analytical challenges that have become a frequent topic in "organoboron compound characterization" searches. Recent improvements in cryoprobe technology have significantly enhanced detection sensitivity for such low-abundance nuclei.

In the context of green chemistry initiatives, 2-cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine represents progress toward more sustainable cross-coupling methodologies. The compound's stability reduces the need for inert atmosphere handling, addressing common queries about "air-tolerant coupling reagents." This characteristic has become increasingly important as laboratories seek to minimize glovebox dependence and reduce organic synthesis waste.

The pharmaceutical industry's shift toward targeted therapies has amplified demand for sophisticated heterocyclic boronic esters like this pyrimidine derivative. Its structural features enable precise molecular recognition in biological systems, particularly in designing protease inhibitors and signal transduction modulators. These applications frequently appear in searches for "next-generation pharmaceutical intermediates" and "bioactive boron compounds."

From a commercial availability standpoint, CAS No. 1402166-11-3 remains a niche product primarily supplied by specialty fine chemical manufacturers. The compound's pricing and custom synthesis options frequently appear in procurement-related searches, reflecting the market's need for reliable sources of high-purity boron reagents. Recent advancements in continuous flow chemistry have begun impacting production scalability for such specialty organoborons.

Looking forward, 2-cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine is poised to play an expanding role in bioconjugation chemistry and theragnostic development. The intersection of its boron neutron capture therapy (BNCT) potential and PET tracer applicability continues to drive research interest, particularly in searches combining "boron in theranostics" and "multifunctional pharmaceutical scaffolds." This dual functionality exemplifies the compound's relevance in contemporary precision medicine initiatives.

• 1235450-87-9(2-ethyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine)
• 1402166-38-4(2-(tetrahydro-2H-pyran-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine)
• 1882114-79-5(Pyrimidine, 2-(1,1-dimethylethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-)
• 1052686-67-5(2-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine)
• 1319255-87-2(2-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]propan-2-ol)
• 1820679-54-6(2-Isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine)
• 2223054-01-9(4-Amino-2-(cyclohexyl)pyrimidine-5-boronic acid pinacol ester)
• 1795453-09-6(2-cyclobutyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine)
• 1375301-91-9(2-cyclopropyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine)
• 1476076-45-5(4,6-dideuterio-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine)