4-CHLORO-2-METHYLPHENYLBORONIC ACID Chemical Properties

Melting point:

193-195°C

Boiling point:

314.9±52.0 °C(Predicted)

Density 

1.26±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

8.47±0.58(Predicted)

color 

White to Almost white

InChIKey

SRXXSLUUAWHGBZ-UHFFFAOYSA-N

CAS DataBase Reference

209919-30-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36/37/39-36

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

• Language:English Provider:ALFA

4-CHLORO-2-METHYLPHENYLBORONIC ACID Usage And Synthesis

Chemical Properties

White solid

Uses

suzuki reaction

Synthesis

The general procedure for the synthesis of 2-methyl-4-chlorophenylboronic acid from 2-bromo-5-chlorotoluene was as follows: first, 13.3 mL (0.1 mol) of 2-bromo-5-chlorotoluene was dissolved in 200 mL of anhydrous tetrahydrofuran (THF), followed by the addition of 27.7 mL (0.12 mol) of triisopropyl borate. After cooling the reaction mixture to -78°C in a dry ice-acetone bath, 48 mL (0.12 mol) of 2.5 M n-butyllithium (n-BuLi, dissolved in hexane) was added slowly dropwise over a period of 1 hour. After completion of the dropwise addition, the dry ice-acetone bath was removed. 150 mL of 3N hydrochloric acid (HCl) was added to the reaction mixture and the resulting mixture was stirred for 1 hour. Subsequently, the separated aqueous layer was extracted twice with 100 mL of ethyl acetate. The organic layers were combined, washed with saturated brine solution and dried with anhydrous magnesium sulfate (MgSO?). After removal of the solvent by filtration under reduced pressure, the residue was recrystallized by 10% ethyl acetate/hexane solvent mixture to give 13.8 g (81% yield) of 2-methyl-4-chlorophenylboronic acid as a white solid. The product was characterized by 1H NMR (300 MHz, CDCl?) with chemical shifts of δ 8.07 (dd, 1H, J = 5.7 Hz, 2.8 Hz), 7.28-7.26 (m, 2H), 2.76 (s, 3H).

References

[1] Patent: WO2005/123054, 2005, A1. Location in patent: Page/Page column 23

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