2-Cyanophenylboronic acid 2,2-dimethylpropanediol-1,3-cyclic ester forms a specialized compound with notable interest for researchers and industry professionals. The name alone hints at its complexity, pulling in elements of cyanophenyl and boronic acid functionalities fused to a diol-derived cyclic structure. Chemists see value in these specific motifs because they influence how the material behaves during organic synthesis or when paired with catalysts. In labs focused on pharmaceuticals or advanced materials, this ester often finds use as a building block, opening doors to unique reaction pathways not easily accessed with simpler boronic acids.
The molecular structure shows a boronic acid group attached to a phenyl ring substituted at the ortho-position with a cyano group, then cyclized with 2,2-dimethylpropanediol leading to a stable yet reactive five-membered cyclic ester. The molecular formula typically runs as C13H16BNO3, reflecting each atom present in the framework. Having worked with cyclic boronic esters before, I see how this ring confers extra stability, which makes purification and storage simpler compared to plain boronic acids. The ring’s steric protection also helps reduce unwanted side reactions during coupling steps.
2-Cyanophenylboronic acid 2,2-dimethylpropanediol-1,3-cyclic ester often appears as a solid at room temperature, resembling off-white to pale yellow flakes or tiny pearls. Density measurements for similar compounds hover around 1.18–1.24 g/cm3, meaning this material is denser than water and settles easily in solution. Some batches present as fine powders, while others pack together into small crystalline chunks. As a solid, it stores easily with minimal caking or degradation, reducing headaches for anyone who has experienced the mess of materials that liquefy or clump unpredictably. In ethanol or other organic solvents, it dissolves to form clear solutions, hinting at the purity and low contamination risk for reactions.
This cyclic ester keeps the reactive boronate moiety, which allows for Suzuki-Miyaura cross-coupling and similar strategies in organic synthesis. The nitrile group further expands its chemistry, inviting nucleophilic attacks or reductive transformations. Through experience, I’ve learned how the added cyclic diol ester helps mask boron’s typical air- and water-sensitivity, making the product more robust during storage and handling. During coupling reactions, the ring pops open at the right time to regenerate the reactive boronic acid spot, efficiently pursuing product formation with fewer by-products.
Suppliers usually offer this ester at high purity (≥98%), ensuring that side reactions don’t interfere in downstream transformations. Available forms include solid flakes, free-flowing powders, and in some labs, pre-weighed pearls for dosing. Popular packaging comes in sealed bottles or tubes lined with moisture-barriers. Storage calls for a cool, dry place away from acids or oxidants, but thanks to the cyclic ester’s resilience, shelf-life exceeds that of many unprotected boronic acids, which deteriorate fast in humidity.
Preparing solutions from this compound can be straightforward. The relatively high density ensures reliable weighing, while its keen solubility in alcohols and polar aprotic solvents cuts prep time. Anyone mixing up a batch for coupling reactions can rely on consistent volumetric measurements, translating to reproducible results in research or production. A liter of solution typically holds the ester at concentrations ranging from 10 g/L to 100 g/L, depending on process needs.
Although not classified among the most hazardous chemicals, exposure to dust or solutions demands care. Its cyanophenyl group serves as a warning flag, as nitriles have been known to cause skin and eye irritation. The boronic ester component, while far less reactive than free boronic acids, can still catalyze unwanted reactions with strong acids or oxidizers. Proper PPE — gloves, goggles, and fume extraction — stand as musts. Spills swept up dry, solvents neutralized and disposed of according to standard industrial protocols. Handling similar chemicals, I found clear labels and real-time communication cut down on accidental exposures, an easy lift with smart checklist routines. Safety Data Sheets (SDS) call out risks of inhalation, noting that in large enough quantities, cyanophenyl compounds pose health risks. Fortunately, routine scale chemists don’t face that level of exposure, but anyone working with kilogram-lots should consult medical resources and have spill kits nearby.
2-Cyanophenylboronic acid 2,2-dimethylpropanediol-1,3-cyclic ester carves out a special spot as a raw material for advanced intermediates in medicinal chemistry and specialty materials development. Its boronic ester handles facilitate bond formations central to the creation of pharmaceuticals, organic electronic materials, and custom polymers. One example stands out — in crafting new treatments for hypertension, I’ve seen this ester used to couple with complex halides, delivering key intermediates with high yields where simpler boronic acids fell short. The chemoselectivity and stability sped up the campaign, slashing bench time and material waste. The modular structure means researchers can tweak substitution patterns as needed, shifting focus between medicinally relevant scaffolds or high-performance organic frameworks.
Customs and shipping recognize 2-cyanophenylboronic acid 2,2-dimethylpropanediol-1,3-cyclic ester under the HS Code 293190, covering other heterocyclic compounds with nitrogen hetero-atom(s) only. This classification smooths global trade, pinpointing tariffs and harmonizing documentation. Anyone familiar with international logistics knows that proper classification avoids costly delays; incorrect HS codes flag shipments for lengthy inspections or rejections.
Lab routines benefit from this compound’s resilience. I recommend storing the material in airtight containers, with a few packets of desiccant to snuff out residual moisture and prevent hydrolysis or clumping. Always record batch numbers and test small samples from any larger shipment before scaling up, especially when target purity or physical form varies. Waste streams, particularly anything with solvent residues, should track into dedicated hazardous material containers for regulated disposal. In my own lab, color-coding containers made finding and tracking this compound easy, especially during hectic synthesis campaigns where mistakes can multiply.
The main challenge lies in balancing material stability with reactivity. Traditional boronic acids often absorb water and degrade, while overly bulky esters lose their desired reactivity. The 2,2-dimethylpropanediol-1,3 cyclic ester navigates this space well, standing up to air and storage but readily ‘uncaging’ in the right reaction conditions. Sourcing reliable material means buying from producers who publish current purity data and transparency in provenance, ensuring batch-to-batch consistency. Utilization in automated synthesizers or flow chemistry systems means suppliers must support bulk packaging formats and include certificates of analysis. A transparent supply chain serving both large pharmaceutical campaigns and bespoke research helps scientists spend less time on quality control and more on breakthroughs.
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