Boronic acid,phenyl CAS NO.98-80-6

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Phenylboronic acid (chemical formula: PhB(OH)2) is an alkylboronic acid obtained by replacing one of the hydroxyl groups in the boronic acid with a phenyl group.

Production method: 1. Within 1 hour, 0.25 mol of phenylmagnesium bromide (about 1 molar solution) is added to a solution of 58 g (0.25 mol) of n-butyl borate dissolved in 100 ml of pure ether. The solution was cooled during the reaction with mechanical stirring and a solid carbon dioxide and acetone bath to maintain the internal temperature between one 70°C and one 75°C. When Grignard's reagent was dropped into the reaction solution, a white precipitate was formed immediately, which slowly dissolved again. After the addition of Grignard's reagent, continue to stir the reaction mixture (at a temperature of 75 ℃) until the precipitate is completely dissolved. The resulting orange solution is slowly warmed to 0°C in a cold water bath (preferably overnight). Under vigorous stirring, the reaction mixture is slowly added to 150 ml of cold 10% sulfuric acid and the ether layer is separated. The aqueous layer is extracted with 2 parts of 100 ml of ether. The original ether layer and the ether extract were combined and the ether was evaporated on a steam bath. The residue, containing phenylboronic acid and n-butanol, was treated with potassium hydroxide solution until the solution was clearly alkaline. Add enough water to form an aqueous layer of about 150 ml below the alcohol layer. By gentle heating under reduced pressure (not exceeding 45°C), the water vapor distillation evaporates the n-butanol, and the distillation is continued by slowly adding warm water as often as necessary until no n-butanol is distilled. Finally, a small amount of biphenyl is evaporated, and the water layer in the distillation bottle is separated from a small amount of viscous solids. The residue is acidified with sulfuric acid until the Congo red paper changes color, and diluted (if necessary) to 150-200 ml. Without separating the precipitate, the mixture is heated to boiling with continued stirring, and after a short time the crystals melt completely and become a heavy insoluble brown oil layer. Pour out the water layer, so that it passes through the folded filter paper. The oil layer is extracted with several 20 ml boiling water, the extract is filtered while hot, combined with the original aqueous layer and crystallized into white needle-like phenylboronic acid after cooling. The product weighs 14-17 g (50-60%) after drying and is no longer refined, and the melting point of 214-216°C (corrected) is measured by capillary tube. From the mother liquor, 1 or 2 grams of impure product can be recovered. The yield is lower (42-47%) when a more concentrated solution of Grignard's reagent is used for bulk preparation. In a similar way, p-tolylboronic acid, p-methoxyboronic acid, etc. can be produced.
2. Laboratory preparations can be made by reacting phenyl Grignard's reagent with boronic acid triglycerides.

Appearance and properties: white to off-white solid 
Density: 1.13g/cm3

Boiling point: 265.9ºC at 760mmHg

Melting point: 216-219 °C (lit.)

Flash point: 114.6ºC

Refractive index: 1.534

Water solubility: 10 g/L (20 ºC)

Storage conditions: ventilated and dry at low temperature, separate from food materials in the warehouse