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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Phenylcarbamic acid esters

Comprehensive Overview of tert-Butyl 5-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (CAS 1186637-38-6)

The compound tert-Butyl 5-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (CAS 1186637-38-6) is a highly specialized boronic ester derivative with significant applications in pharmaceutical research and organic synthesis. Its unique structure, featuring a fluorophenyl group and a dioxaborolane moiety, makes it a valuable intermediate in the development of targeted therapies, particularly in the field of cancer research and protease inhibition. The compound's CAS number 1186637-38-6 is frequently searched in academic and industrial databases, reflecting its growing relevance in modern chemistry.

One of the key reasons for the popularity of tert-Butyl 5-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate lies in its role as a Suzuki-Miyaura coupling reagent. This reaction, a cornerstone of cross-coupling chemistry, is widely used to construct biaryl structures, which are prevalent in many FDA-approved drugs. Researchers often inquire about the synthetic routes and purification methods for this compound, as its boronate ester group requires careful handling to maintain stability. Recent publications highlight its utility in creating kinase inhibitors, a hot topic in precision medicine.

From a structural-activity relationship (SAR) perspective, the 5-fluoro substitution on the phenyl ring enhances the compound's bioavailability and metabolic stability, addressing common challenges in drug design. The tert-butyl carbamate protecting group further improves solubility, a feature frequently discussed in formulation optimization forums. Laboratories working on PET radiotracers also show interest in this compound due to the potential of its fluorine-18 analogs for molecular imaging.

In green chemistry initiatives, CAS 1186637-38-6 has gained attention for its compatibility with microwave-assisted synthesis, reducing reaction times and energy consumption. This aligns with the industry's shift toward sustainable manufacturing practices. Analytical chemists emphasize the importance of HPLC purity testing for this compound, as even minor impurities can affect downstream catalytic efficiency in coupling reactions.

The stability of tert-Butyl 5-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate under various pH conditions is another frequently researched aspect, particularly for oral drug delivery applications. Its crystallinity and polymorph screening data are often requested by process chemistry teams scaling up production. Notably, patent databases reveal its inclusion in several drug candidate pipelines targeting autoimmune disorders.

Emerging trends in AI-assisted molecular design have brought new focus to this compound's computational descriptors, with machine learning models predicting its reactivity in multi-component reactions. The 4,4,5,5-tetramethyl-1,3,2-dioxaborolane group's rotational barriers are studied using DFT calculations, providing insights for conformational analysis in related boron-containing pharmaceuticals.

For quality control purposes, the compound's NMR fingerprint (particularly the characteristic boron-11 signal) serves as a critical identification marker. Supply chain specialists monitor its batch-to-batch variability, given the stringent requirements of GMP manufacturing environments. The lyophilization behavior of its derivatives is another area of active investigation in biopharmaceutical circles.

In conclusion, tert-Butyl 5-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (CAS 1186637-38-6) represents a versatile building block at the intersection of medicinal chemistry and materials science. Its ongoing applications in next-generation therapeutics and catalysis research ensure its continued importance in scientific literature and industrial workflows.

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