2-Chlorophenylboronic acid Chemical Properties

Melting point:

92-102 °C (lit.)

Boiling point:

306.3±44.0 °C(Predicted)

Density 

1.32±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in DMSO, Methanol.

form 

Crystalline Powder

pka

8.23±0.58(Predicted)

color 

White

BRN 

3030414

InChI

InChI=1S/C6H6BClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4,9-10H

InChIKey

RRCMGJCFMJBHQC-UHFFFAOYSA-N

SMILES

B(C1=CC=CC=C1Cl)(O)O

CAS DataBase Reference

3900-89-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26-36

WGK Germany 

3

TSCA 

No

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Chlorophenylboronic acid Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

suzuki reaction

Uses

2-Chlorophenylboronic Acid used in the preparation of imidazo[1,2-a]pyridine amides which has tuberculostatic activity.

Synthesis

Step (f): n-BuLi (2.5 M, n-hexane solution, 2.5 mL, 1.2 eq., 6.3 mmol) was slowly added dropwise under nitrogen protection to a solvent mixture of toluene and THF (4: 1, 10 mL, 10 mL) containing 2-bromo chlorobenzene (I) (1 g, 0.6 mL, 5.2 mmol) and triisopropyl borate (1.44 mL, 1.2 eq., 6.27 mmol). 1, 10 mL) in a reaction temperature of -70°C and a dropwise addition time of 1 hour. After the dropwise addition, the reaction mixture was continued to be stirred at -70°C for 0.5 hr. Subsequently, the reaction system was slowly warmed to -20 °C and the reaction was quenched by the addition of 2N HCl solution (5 mL). After the reaction mixture was brought to room temperature, it was extracted with dichloromethane. The organic phases were combined, dried and concentrated to give a white solid. The solid was purified by recrystallization from acetonitrile to give the target product 2-chlorophenylboronic acid in 98% yield (800 mg).

References

[1] Patent: WO2013/90725, 2013, A1. Location in patent: Page/Page column 68
[2] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 590 - 603
[3] Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5394 - 5397

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