9-Anthraceneboronic acid

Description

9-Anthraceneboronic acid is a boronic acid compound mainly used as an organic synthesis and reaction reagent. The addition of 9-Anthraceneboronic acid introduces a borate ester bond and an anthracene functional group into ordinary polyvinyl alcohol, which can be used to prepare the composite material poly(vinyl alcohol) anthraceneboronic acid (PVA-ABA), which is suitable for sustainable engineering applications due to its high mechanical strength and toughness, good water resistance, chemical durability, and ease of recycling. It can also be used to prepare stimuli-responsive polymeric materials and highly efficient luminescent materials.

Chemical properties

Tan solid

The Uses of 9-Anthraceneboronic acid

suzuki reaction

Synthesis

9-bromoanthracence (10.0 g, 38.9 mmol) was dissolved in an anhydrous THF solution (500 mL) and stirred at ?78C. Then, 1.6 M n-BuLi (29.3 mL,46.7 mmol) was added. Triethyl borate (9.3 mL, 54.5 mmol) was added to the reaction after 30 min. After the reaction, the solution was acidified with 2 N HCl solution at room temperature and extracted with ethyl acetate and water. The organic layer was dried with anhydrous MgSO4 and filtered. The solution was evaporated. The residue was dissolved in hexane and added to ethyl acetate. The precipitate was filtered and washed with hexane to obtain a beige compound 9-Anthraceneboronic acid (7.70 g, 89 percent).

Purification Methods

Crystallise the boronic acid from dilute HCl (m 180-184o). The disodium salt has m 209-213o. [Beilstein 16 IV 1679.]