4-(NAPHTHALEN-1-YL)PHENYLBORONIC ACID Chemical Properties

Boiling point:

449.4±48.0 °C(Predicted)

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

soluble in Tetrahydrofuran

form 

powder to crystal

pka

8.58±0.16(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C16H13BO2/c18-17(19)14-10-8-13(9-11-14)16-7-3-5-12-4-1-2-6-15(12)16/h1-11,18-19H

InChIKey

BQHVXFQXTOIMQM-UHFFFAOYSA-N

SMILES

B(C1=CC=C(C2=C3C(C=CC=C3)=CC=C2)C=C1)(O)O

Safety Information

HS Code 

2931900090

4-(NAPHTHALEN-1-YL)PHENYLBORONIC ACID Usage And Synthesis

Application

4-(1-Naphthyl)phenylboronic acid is an acid derivative that can be used as an intermediate in organic synthesis.

Chemical Properties

off-white powder

Synthesis

A mixed solution of 208.8 g (737.4 mmol) of 1-(4-bromophenyl)naphthalene with 2.1 L of anhydrous tetrahydrofuran (THF) was cooled to -60 °C under argon protection. Subsequently, 567 mL (884.9 mmol) of 1.56 M n-butyllithium hexane solution was added slowly dropwise under stirring conditions. After the dropwise addition was completed, the reaction mixture was continued to be stirred at -60 °C for 2 hours. Maintaining the temperature at -60 °C, 416 g (2.21 mol) of triisopropyl borate was added dropwise to the reaction system. After completion of the dropwise addition, the reaction mixture was gradually warmed to room temperature and stirred for 17 hours. At the end of the reaction, an aqueous hydrochloric acid solution was added to the mixture and stirred for 1 hour at room temperature. The reaction mixture was extracted with toluene, and the aqueous phase was separated and discarded. The organic phase was dried with 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 4-(1-naphthyl)phenylboronic acid in 67% yield.

References

[1] Patent: US2010/331585, 2010, A1. Location in patent: Page/Page column 96-97

4-(NAPHTHALEN-1-YL)PHENYLBORONIC ACID (870774-25-7)Related Product Information

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