3-(naphthalene-2-yl)phenylboronic acid Chemical Properties

Boiling point:

486.0±48.0 °C(Predicted)

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to crystal

pka

8.27±0.19(Predicted)

color 

White to Almost white

Safety Information

HS Code 

2931.90.9051

3-(naphthalene-2-yl)phenylboronic acid Usage And Synthesis

Synthesis

Under argon protection, 212 g (748 mmol) of 3-(2-naphthyl)bromobenzene was mixed with 3 L of anhydrous tetrahydrofuran (THF) and cooled to -10 °C. Simultaneously, 600 mL (948 mmol) of hexane was cooled to 0 °C. Under stirring, 1.6 M hexane solution of n-butyllithium was slowly added dropwise to the reaction mixture. After the dropwise addition was completed, the reaction mixture was continued to be stirred at 0 °C for 2 hours. Subsequently, the reaction system was cooled to -78 °C and 450 g (2.39 mol) of triisopropyl borate was added slowly dropwise. After completion of the dropwise addition, the reaction mixture was gradually warmed to room temperature and stirred for 17 hours. After completion of the reaction, dilute aqueous hydrochloric acid solution was added to the mixture and stirred for 1 hour at room temperature. Next, 3 L of toluene was added for extraction to separate the organic and aqueous phases. The organic phase was dried with anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The resulting solid was purified by recrystallization from toluene to give 126 g of 3-(2-naphthyl)phenylboronic acid in 67% yield.

References

[1] Patent: US2010/331585, 2010, A1. Location in patent: Page/Page column 95
[2] Patent: WO2007/86695, 2007, A1. Location in patent: Page/Page column 72-73

3-(naphthalene-2-yl)phenylboronic acid(870774-29-1)Related Product Information

• 4-(NAPHTHALEN-1-YL)PHENYLBORONIC ACID
• 2-(naphthalen-2-yl)phenylboronic acid
• 4-(NAPHTHALEN-2-YL)PHENYLBORONIC ACID
• BORONIC ACID, [3-(1-NAPHTHALENYL)PHENYL]-