Overview
Phenylboronic acid is an aromatic boronic acid with the formula C6H7BO2. It is a versatile reagent in organic chemistry, particularly in cross-coupling reactions like the Suzuki-Miyaura coupling. Its ability to form stable complexes with diols makes it useful in sensors and diagnostics. The compound is commercially available and widely used in pharmaceutical and material science research. Due to its reactivity and stability, phenylboronic acid is a preferred choice for synthesizing biaryl compounds, which are key intermediates in drug development. Its relatively low toxicity and ease of handling further enhance its industrial applicability.
Physical and Chemical Properties
Phenylboronic acid appears as a white to off-white crystalline powder with a molecular weight of 121.93 g/mol. It has a melting point range of 216-219 °C and a density of 1.08 g/cm³. The compound is soluble in polar solvents like water, methanol, and ethanol but has limited solubility in non-polar solvents such as ether. Chemically, phenylboronic acid is stable under normal conditions but reacts with diols, amines, and other nucleophiles. This reactivity is exploited in various synthetic applications, including the formation of boronate esters. Its stability in aqueous solutions makes it suitable for biological and environmental applications.
Main Applications
Phenylboronic acid is primarily used in Suzuki-Miyaura cross-coupling reactions to form carbon-carbon bonds, a critical step in synthesizing pharmaceuticals, agrochemicals, and advanced materials. It serves as a key intermediate in producing drugs like losartan and other angiotensin II receptor antagonists. Beyond pharmaceuticals, the compound is used in polymer chemistry to create boronate-containing polymers with unique properties. It also finds applications in glucose sensing due to its ability to bind diols, making it useful in medical diagnostics and biosensors. Additionally, it is employed in the synthesis of fluorescent dyes and other specialty chemicals.
Safety and Storage
Phenylboronic acid is classified as an irritant and can cause skin, eye, and respiratory tract irritation. Proper personal protective equipment (PPE), including gloves and goggles, should be worn when handling the compound. Work should be conducted in a well-ventilated area or under a fume hood to minimize exposure. Storage conditions are critical to maintaining the compound's stability. It should be kept in a cool, dry place, sealed tightly to prevent moisture absorption. Incompatible materials include strong oxidizing agents, which can lead to hazardous reactions. Spills should be contained and cleaned up immediately using appropriate absorbents.
B2B Procurement Guide
When procuring phenylboronic acid, buyers should prioritize purity (typically ≥98%), packaging integrity (sealed, moisture-proof containers), and supplier reliability. Certificates of Analysis (CoA) and compliance with international standards (e.g., ISO, USP) are essential for quality assurance. Bulk purchases may offer cost advantages, but storage capacity and shelf life should be considered. Lead times can vary, so planning ahead is advisable. Suppliers with a track record in fine chemicals and organoboron compounds are preferred. For specialized applications, custom synthesis or tailored formulations may be available from select manufacturers.
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