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4-Chloro-2-methylphenylboronic acid

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4-Chloro-2-methylphenylboronic acid manufacturers

4-Chloro-2-methylphenylboronic acid Basic information
Product Name:4-Chloro-2-methylphenylboronic acid
Synonyms:AKOS BRN-0229;4-CHLORO-O-TOLUENEBORONIC ACID;4-CHLORO-2-METHYLBENZENEBORONIC ACID;4-Chloro-2-Methylphenylboronic;4-chloro-o-tolylboronic acid;4-Chloro-2-methylphenylboronic acid ,98%;4-Chloro-2-Methylphenylboronic Acid (contains varying aMounts of Anhydride);4-Chloro-2-methylbenzeneboronic Acid 4-Chloro-o-tolylboronic Acid
CAS:209919-30-2
MF:C7H8BClO2
MW:170.4
EINECS:
Product Categories:Aryl;Boronic acid;Organoborons;blocks;BoronicAcids
Mol File:209919-30-2.mol
4-Chloro-2-methylphenylboronic acid Structure
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
pka8.47±0.58(Predicted)
color White to Almost white
InChIKeySRXXSLUUAWHGBZ-UHFFFAOYSA-N
CAS DataBase Reference209919-30-2(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 Information
ProviderLanguage
ALFA English
4-Chloro-2-methylphenylboronic acid Usage And Synthesis
Chemical PropertiesWhite solid
Usessuzuki reaction
Synthesis
1-Bromo-4-chloro-2-methylbenzene

14495-51-3

4-CHLORO-2-METHYLPHENYLBORONIC ACID

209919-30-2

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
4-Chloro-2-methylphenylboronic acid Preparation Products And Raw materials
Raw materialsTetrahydrofuran-->n-Butyllithium-->Triisopropyl borate-->1-Bromo-4-chloro-2-methylbenzene-->Hydrochloric acid-->Water-->Hexane
Preparation Products3-(4-Chloro-2-methylphenyl)benzoic acid
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