4-Chlorophenylboronic acid, pinacol ester

Name: 4-Chlorophenylboronic acid, pinacol ester
SKU: ACM195062614-1
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Catalog NumberACM195062614-1

CAS Number195062-61-4

CategorySalt

Synonyms

632724_ALDRICH, BM129, 4-Chlorophenylboronic acid pinacol ester, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)chlorobenzene, 195062-61-4

IUPAC Name

2-(4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Molecular Weight

238.52

Molecular Formula

C₁₂H₁₆BClO₂

Canonical SMILES

B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)Cl

InChI Key

NYARTXMDWRAVIX-UHFFFAOYSA-N

Boiling Point

308.7ºC at 760mmHg

Melting Point

50-55ºC(lit.)

Flash Point

>230

Purity

98%

Density

1.1g/cm³

Application

4-Chlorophenylboronic acid pinacol ester serves as a versatile reagent with numerous applications in organic synthesis. It is primarily utilized in Suzuki-Miyaura cross-coupling reactions to form carbon-carbon bonds through its interaction with various aryl halides in the presence of palladium catalysts. This compound is also employed in the preparation of 2-(4-chlorophenyl)-4H-chromen-4-one by reacting with 4-chromanone via a one-pot palladium-catalyzed process that involves dehydrogenation and oxidative boron-Heck coupling. Additionally, it plays a crucial role in ligand-enabled C-H bond activation reactions using palladium catalysts and is instrumental in the synthesis of biaryl amides through copper-catalyzed C-H bond coupling with aryl arylamides.

Exact Mass

238.09300

Hazard Statements

Xn: Harmful;

Safety Description

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