(4-CHLORO-3-METHOXYPHENYL)BORONICACID Chemical Properties

Melting point:

151°C(lit.)

Boiling point:

341.7±52.0 °C(Predicted)

Density 

1.32±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

7.91±0.10(Predicted)

color 

White to Almost white

Safety Information

HS Code 

2931900090

(4-CHLORO-3-METHOXYPHENYL)BORONICACID Usage And Synthesis

Uses

4-Chloro-3-methoxyphenylboronic acid

Synthesis

The general procedure for the synthesis of 4-chloro-3-methoxyphenylboronic acid from 5-bromo-2-chloroanisole was as follows: n-butyllithium (8.7 mL, 1.6 M hexane solution, 14 mmol) was added slowly and dropwise to a mixture of toluene/THF (16/6 mL) of 4-bromo-1-chloro-2-methoxybenzene (2.2 g, 9.9 mmol) at -78 °C. After the reaction mixture was stirred at -78 °C for 30 min, trimethyl borate (2.2 mL, 19.8 mmol) was added. Subsequently, the reaction system was slowly warmed to room temperature and stirring was continued overnight. Upon completion of the reaction, the reaction was quenched with 1 M HCl (15 mL). The organic layer was separated and dried with anhydrous sodium sulfate. After removing the solvent under reduced pressure, the crude product was purified by fast column chromatography to afford the target compound 4-chloro-3-methoxyphenylboronic acid (1.2 g, 65% yield) as a white solid.1H NMR (400 MHz, CD3OD) δ ppm: 3.87 (s, 3H), 7.11 (d, J=7.83 Hz, 1H), 7.20 (s, 1H), 7.29 ( d, J=7.83Hz, 1H).

References

[1] Patent: US2010/227894, 2010, A1. Location in patent: Page/Page column 35
[2] Patent: US2007/3539, 2007, A1. Location in patent: Page/Page column 77
[3] Patent: WO2015/58084, 2015, A1. Location in patent: Paragraph 0331

(4-CHLORO-3-METHOXYPHENYL)BORONICACID(89694-47-3)Related Product Information

• 2-Chloro-3-methoxyphenylboronic acid
• 4-(1-Hydroxyethyl)phenylboronic acid
• 3-(1-Hydroxyethyl)phenylboronic acid
• Boronic acid, [4-(difluoromethoxy)phenyl]- (9CI)
• 2,5-Dibromophenylboronicacid
• 2-(Difluoromethoxy)-benzeneboronic acid