(4-Chloro-3-methoxyphenyl)boronicacid

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(4-Chloro-3-methoxyphenyl)boronicacid Basic information
Product Name:(4-Chloro-3-methoxyphenyl)boronicacid
Synonyms:4-Chloro-3-methoxyphenylboronic acid, >=98%;B-(4-Chloro-3-methoxy-phenyl)boronic acid;4-Chloro-3-methoxybenzeneboronicacid;Boronic acid, (4-chloro-3-Methoxyphenyl)-;4-Chloro-3-methoxyphenylboronic Acid (contains varying amounts of Anhydride);4-Chloro-3-methoxyphenylboronic Acid (contains varyi;Boronic acid, B-(4-chloro-3-methoxyphenyl)-
CAS:89694-47-3
MF:C7H8BClO3
MW:186.4
EINECS:
Product Categories:
Mol File:89694-47-3.mol
(4-Chloro-3-methoxyphenyl)boronicacid Structure
(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
pka7.91±0.10(Predicted)
color White to Almost white
Safety Information
HS Code 2931900090
MSDS Information
(4-Chloro-3-methoxyphenyl)boronicacid Usage And Synthesis
Uses4-Chloro-3-methoxyphenylboronic acid
Synthesis
5-BROMO-2-CHLOROANISOLE

16817-43-9

(4-CHLORO-3-METHOXYPHENYL)BORONICACID

89694-47-3

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
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