4-Chloro-2-methoxyphenylboronic acid Chemical Properties

Melting point:

128-134°C

Boiling point:

345.4±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

8.42±0.58(Predicted)

color 

White to Almost white

InChI

InChI=1S/C7H8BClO3/c1-12-7-4-5(9)2-3-6(7)8(10)11/h2-4,10-11H,1H3

InChIKey

NZRRMTBNTSBIFH-UHFFFAOYSA-N

SMILES

B(C1=CC=C(Cl)C=C1OC)(O)O

CAS DataBase Reference

762287-57-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2931900090

4-Chloro-2-methoxyphenylboronic acid Usage And Synthesis

Uses

suzuki reaction

Synthesis

General procedure for the synthesis of 4-chloro-2-methoxyphenylboronic acid: preparation of intermediate I-1. 22.1 g (100 mmol) of 2-bromo-5-chloroanisole was dissolved in 500 mL of tetrahydrofuran (THF) and stirred for 10 min at -78 °C and protected by nitrogen (N2). Subsequently, 44 mL of a 2.5 M solution of n-butyllithium (n-BuLi) was slowly added through a dropping funnel and stirring was continued for 30 minutes. Next, 10.4 g (110 mmol) of trimethyl borate was slowly added dropwise, and after completion of the dropwise addition, the reaction mixture was warmed to room temperature and stirred for 3 hours. After completion of the reaction, the reaction was quenched with 300 mL of 1 M hydrochloric acid (HCl) and the organic layer was extracted three times with diethyl ether and washed with water. The organic layers were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography to afford 13.61 g of Intermediate I-1 (73 mmol, 73% yield). The resulting compound was characterized by mass spectrometry (MS/FAB): theoretical value of [M+H]+ (C7H8BClO3) 186.40, measured value 186.47.

References

[1] Organic Letters, 2016, vol. 18, # 15, p. 3630 - 3633
[2] Patent: US2016/190448, 2016, A1. Location in patent: Paragraph 0261; 0262; 0263
[3] Patent: US2016/190449, 2016, A1. Location in patent: Paragraph 0271; 0272

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