Ethenylboronic acid

Updated: 2026-07-19

Overview

Vinylboronic acid (C2H5BO2) is an organoboron compound featuring a vinyl group attached to a boronic acid functional group. It is a versatile reagent in organic chemistry, particularly valued for its role in cross-coupling reactions such as the Suzuki-Miyaura coupling. This reaction is pivotal in forming carbon-carbon bonds, enabling the synthesis of complex organic molecules, including pharmaceuticals and agrochemicals. The compound is commercially available but requires careful handling due to its sensitivity to moisture and air. Its reactivity and stability are influenced by storage conditions, making proper procurement and handling essential for optimal performance in laboratory and industrial settings.

Physical and Chemical Properties

Vinylboronic acid typically appears as a white to off-white crystalline powder. It has a molecular weight of 71.87 g/mol and a melting point range of 75-80°C. The compound is soluble in water and common organic solvents like ethanol, tetrahydrofuran (THF), and dimethyl sulfoxide (DMSO). Key chemical properties include its sensitivity to air and moisture, which can lead to decomposition or reduced reactivity. The boronic acid group (-B(OH)2) is pivotal for its role in cross-coupling reactions, where it acts as a nucleophile to form new C-C bonds. Stability can be improved by derivatization (e.g., as a boronic ester) or by storing under inert conditions.

Main Applications

The primary application of vinylboronic acid is in the Suzuki-Miyaura coupling reaction, a widely used method for forming carbon-carbon bonds in organic synthesis. This reaction is essential in the production of pharmaceuticals, agrochemicals, and advanced materials. Additionally, vinylboronic acid serves as a building block for synthesizing vinyl-substituted compounds, which are intermediates in polymer chemistry and medicinal chemistry. Its utility extends to asymmetric synthesis and catalysis, where it participates in stereoselective transformations. The compound’s versatility makes it a staple in research and industrial laboratories focused on fine chemical production.

Safety and Storage

Vinylboronic acid is classified as an irritant, posing risks to skin, eyes, and respiratory systems. Proper personal protective equipment (PPE), including gloves and goggles, is mandatory during handling. Work should be conducted in a fume hood to minimize inhalation exposure. Storage requires an inert atmosphere (e.g., nitrogen or argon) in a tightly sealed container to prevent degradation. Moisture-sensitive compounds like this should be kept in a cool, dry place, ideally with desiccants. Disposal must comply with local regulations for boron-containing waste to avoid environmental contamination.

B2B Procurement Guide

When procuring vinylboronic acid, prioritize suppliers with a track record of reliability and quality certifications. Key specifications to verify include purity (≥95% is typical for most applications), packaging (sealed under inert gas), and batch consistency. Price varies based on quantity and purity, with bulk purchases often offering cost savings. Consider lead times and logistical requirements, as air-sensitive compounds may require specialized shipping conditions. For R&D use, smaller quantities from reputable chemical distributors are advisable, while industrial-scale buyers should negotiate long-term supply agreements to ensure stability.