4-Carboxyphenylboronic acid 1,3-propanediol cyclic ester is a condensed organic molecule, formed by merging a boronic acid with phenyl functionality and 1,3-propanediol through a cyclic ester bond. Chemists look at it as an intermediate in organic synthesis or as a specialty building block, especially in pharmaceutical research or advanced materials. This substance emerges as more than just another compound; its structure delivers selectivity and unique reactivity in chemical transformations, especially where boronic acids typically shine, like Suzuki reactions or cross-coupling processes.
Its backbone includes a phenyl ring, carboxyl group, boronic acid functionality, and a five-membered dioxaborolane ring closed by propanediol. Chemical formula for the cyclic ester generally reads as C11H13BO5. The structure stabilizes the boronic acid site, which can reduce hydrolysis and increase shelf life compared to the free boronic acid. This matters to bench chemists trying to avoid frustrating degradation. Boron, carbon, hydrogen, and oxygen atoms form a stable scaffold, promoting easier storage and transport. Molecular weight sits around 236 to 238 g/mol, so calculations remain straightforward when batch planning or scaling up.
You can spot this compound in various forms: solid flakes, crystalline powder, or, less commonly, small pearls. Appearance ranges from off-white to pale yellow, depending on purity. Its density aligns with other similar cyclic boronate esters, close to 1.27 g/cm3. Handling as a powder gives convenience for accurate weighing, but flakes and crystals often minimize dust and improve safety. Solubility varies: it dissolves in polar solvents like DMSO, DMF, or acetone; water resistance stays moderate due to the cyclic ester bond, preventing quick hydrolysis. Those moving solutions in the lab notice an easier process, less risk of clumping or dropping out compared to stickier or hygroscopic powders.
This ester carries over the notable reactivity of arylboronic acids, including affinity for diol exchange, ester hydrolysis, and involvement in C–C coupling reactions. Still, the cyclic structure tempers this reactivity, acting almost like a safekeeping shell until harsher conditions come along. Such a design opens pathways for controlled delivery or gradual release of active boronic acids in more complex syntheses. The carboxyl group's presence increases polarity and offers extra handles for further transformations, such as amidation or salt formation. For some in research or chemical supply, these aspects matter more than a standard boronic acid due to extended usability or added functions in multi-step chemistry routes.
Manufacturers often specify purity at 98% or better, confirmed by NMR and HPLC. Melting point falls between 128–135°C, letting users detect impurities as deviations from these values. Particle size sits in the 40–120 mesh range, balancing flow with dispersibility. Typical packaging ranges from small bottles (10 g, 50 g) for research use to kilogram lots for industrial trial. It stores best in cool, dry places—original sealed containers keep it from absorbing atmospheric water that could start slow hydrolysis.
Customs classify this compound under HS Code 2931.39 for organo-boron compounds, affecting import and regulatory paperwork. Raw materials begin with phenylboronic acid and 1,3-propanediol. The synthetic route leans on acid-catalyzed esterification—no rare metals, so material costs and environmental concerns land at a manageable level for both academic labs and commercial suppliers.
The ester does not fall under major hazardous chemical categories, but standard laboratory care goes a long way. It can cause mild irritation on contact with skin or eyes. Dust may subtly irritate inhaled airways, so gloves and eye protection qualify as everyday gear, especially during weighing or transfer. Spills get swept up without drama, but clean benches and good ventilation help keep risk low. Waste disposal rides under local guidance for boron-containing organic waste, keeping compliance straightforward. Everyone in chemical work knows safety lapses take only one mistake; safe handling habits make long-term work sustainable.
Chemists choose this ester both for solid-phase applications and for solution-phase transformations. As a solid, it persists as defined crystals or friable flakes that pour and measure easily. In solution, it offers a stable boron center, ready for selective reactions without unwanted byproducts from early hydrolysis. Its stable form means shipments from manufacturer to user don’t bring surprises like clumped material or decomposed contaminants. Users working up solutions for reactions or screenings value the dependable performance—pain points like batch inconsistency or tricky dissolution take a back seat.
4-Carboxyphenylboronic acid 1,3-propanediol cyclic ester stands as more than just another line on a reagent catalog. Its structure, stability, and tunable functionality deliver consistent results where basic boronic acids can fall short. Ongoing improvements in scale-up and purification shave costs and lift reliability at different levels of the supply chain. For those developing new drugs, materials, or research scaffolds, working with a stable cyclic boronate improves project flow, cutting time lost to troubleshooting or inconsistent behavior. Tracing each part of its production and use suggests lasting value for anyone invested in specialty chemicals or modern organic synthesis.
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