Overview
(E)-1-Pentenylboronic Acid Pinacol Ester is an organoboron compound primarily employed in cross-coupling reactions, notably the Suzuki-Miyaura reaction. Its pinacol ester group enhances stability, making it a preferred reagent in fine chemical synthesis. The compound’s (E)-alkenyl structure is critical for constructing complex organic frameworks in pharmaceuticals and agrochemicals. As a boron-containing intermediate, it enables the formation of carbon-carbon bonds under mild conditions. Its utility in iterative synthesis and modular approaches has made it indispensable in medicinal chemistry and material science research.
Physical and Chemical Properties
The compound typically appears as a colorless to pale yellow liquid with a molecular weight of 196.10 g/mol. It is soluble in organic solvents like tetrahydrofuran (THF) and dichloromethane (DCM) but reacts with water or protic solvents, necessitating anhydrous handling. Its density is approximately 0.89 g/cm³, and it is highly sensitive to air and moisture, which can lead to decomposition. The pinacol ester group stabilizes the boronic acid moiety, preventing dimerization and extending shelf life when stored properly under inert conditions.
Main Applications
This reagent is pivotal in Suzuki-Miyaura cross-coupling reactions, facilitating the synthesis of biaryl and styrene derivatives used in drug development (e.g., kinase inhibitors) and crop protection chemicals. Its (E)-alkenyl group allows stereoselective construction of conjugated systems in polymers and OLED materials. In agrochemicals, it aids in creating bioactive molecules with tailored properties. The compound’s versatility also extends to academic research, where it serves as a building block for complex natural product synthesis and catalysis studies.
Safety and Storage
Due to its flammability and moisture sensitivity, the compound requires strict handling protocols. Use personal protective equipment (PPE), including nitrile gloves and safety goggles, and work in a well-ventilated fume hood to avoid inhalation or skin contact. Storage must be under inert gas (N2 or Ar) at 2-8°C to prevent degradation. Bulk quantities should be shipped with cold packs and desiccants. Spills should be neutralized with inert absorbents and disposed of as hazardous waste.
B2B Procurement Guide
When sourcing (E)-1-Pentenylboronic Acid Pinacol Ester, prioritize suppliers with certified analytical data (NMR, HPLC) to verify purity (>95%). Batch-to-batch consistency is critical for reproducibility in industrial applications. Negotiate bulk discounts for orders above 100g, but confirm cold-chain logistics for stability. Lead times may vary; specialty suppliers often require 2-4 weeks for synthesis. Consider regional regulations (e.g., REACH, TSCA) for international shipments.
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