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Comprehensive Guide to tert-butyl 2-(tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylate (CAS No. 2071192-58-8)

tert-butyl 2-(tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylate (CAS No. 2071192-58-8) is a highly versatile boron-containing compound widely used in organic synthesis, pharmaceutical research, and material science. Its unique structure, featuring a piperidine core and a dioxaborolane moiety, makes it a valuable intermediate for Suzuki-Miyaura coupling reactions, a topic frequently searched by chemists and researchers. The compound's CAS number 2071192-58-8 is often queried in databases for precise identification, reflecting its growing importance in modern chemistry.

In recent years, the demand for boronic acid derivatives like this compound has surged due to their role in drug discovery and bioconjugation. Researchers exploring proteolysis targeting chimeras (PROTACs) or covalent inhibitors often seek such reagents. The tert-butyloxycarbonyl (Boc) protecting group in this molecule enhances its stability, a feature highlighted in many organic synthesis forums and patent applications. Its compatibility with transition metal catalysis aligns with current trends in sustainable chemistry, addressing frequent search queries about green synthesis methods.

The compound's tetramethyl-1,3,2-dioxaborolane subunit contributes to improved solubility in organic solvents compared to free boronic acids, a property discussed in solubility enhancement research. This characteristic makes it particularly useful for high-throughput screening applications, where consistent reagent behavior is critical. Many medicinal chemistry publications reference similar structures when optimizing bioavailability or blood-brain barrier penetration, common challenges in CNS drug development.

From a synthetic perspective, the piperidine-boronate ester structure enables diverse transformations. Recent scientific literature shows increasing use of such compounds in peptide modification and biomarker labeling. The CAS 2071192-58-8 substance often appears in studies about click chemistry and bioorthogonal reactions, reflecting its compatibility with modern chemical biology techniques. Its stability under physiological conditions makes it suitable for in vivo imaging probe development, another hot topic in current research.

Quality control aspects of tert-butyl 2-(tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylate are frequently discussed in analytical chemistry circles. Proper characterization requires advanced techniques like NMR spectroscopy (particularly 11B NMR) and mass spectrometry, addressing common questions about boron compound analysis. The compound's shelf life and storage conditions (typically under inert atmosphere) are practical concerns often raised in laboratory management discussions.

In material science applications, this boronate ester's potential extends to organic electronics and polymer modification. Its ability to participate in cross-coupling reactions makes it valuable for creating π-conjugated systems, a subject with growing interest in OLED development research. The compound's thermal stability profile, often verified by TGA analysis, is crucial for these high-temperature applications.

The pharmaceutical industry values this intermediate for constructing heterocyclic scaffolds present in many FDA-approved drugs. Its chiral piperidine structure is particularly relevant for asymmetric synthesis of bioactive molecules, answering frequent queries about chiral building blocks. Recent patent analyses reveal its use in developing kinase inhibitors and GPCR modulators, demonstrating its importance in addressing undruggable targets.

Environmental considerations regarding boron-containing compounds have led to improved synthetic protocols for CAS 2071192-58-8. Modern catalytic methods minimize heavy metal residues, responding to green chemistry initiatives. The compound's atom economy in coupling reactions makes it attractive for industrial-scale production, a practical concern frequently searched by process chemists.

For researchers investigating structure-activity relationships, this boronate ester offers precise molecular editing capabilities. Its applications in DNA-encoded library synthesis and fragment-based drug discovery demonstrate its relevance in cutting-edge pharmaceutical innovation. The compound's cLogP and hydrogen bond acceptor/donor properties are often calculated in drug design software, addressing common ADME prediction questions.

In academic settings, tert-butyl 2-(tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylate serves as an excellent teaching tool for demonstrating protecting group strategies and organoboron chemistry. Its manipulation illustrates key concepts in retrosynthetic analysis, making it valuable for graduate-level organic chemistry education. Safety data sheets properly address handling procedures, ensuring compliance with laboratory safety standards.

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