4-Chlorophenylboronic acid

• CAS: 1679-18-1
• Catalog Number: ACM1679181
• Category: Boronic Acids
• Molecular Weight: 156.37
• Molecular Formula: C6H6BClO2
• Synonyms: B-(4-Chlorophenyl)boronic acid
• IUPAC Name: (4-chlorophenyl)boronic acid
• Canonical SMILES: B(C1=CC=C(C=C1)Cl)(O)O
• InChI: InChI=1S/C6H6BClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
• InChI Key: CAYQIZIAYYNFCS-UHFFFAOYSA-N
• Boiling Point: 295.4±42.0 °C
• Melting Point: 284-289 °C (lit.)
• Density: 1.32±0.1 g/ml
• Application: 4-Chlorophenylboronic acid serves as a versatile reactant in various chemical reactions, particularly in organometallic and cross-coupling processes. This white or off-white crystalline powder is moderately soluble in water and readily dissolvable in strong polar organic solvents, making it valuable in numerous synthetic applications. It plays a key role in palladium-catalyzed processes such as direct arylation, cyclopalladation, and tandem-type oxidative Heck reactions. Additionally, it is utilized in copper-mediated fluoroalkylation and ligand-free copper-catalyzed coupling reactions. Its utility extends to ruthenium-catalyzed direct arylation and regioselective Suzuki-Miyaura and Sonogashira cross-coupling reactions. Furthermore, 4-Chlorophenylboronic acid is instrumental in synthesizing compounds like substituted diarylmethylidenefluorenes, Baclofen lactam, and palladium(II) thiocarboxamide complexes, as well as biaryls through reactions with aryl chlorides, bromides, and iodides.
• Complexity: 102
• Covalently-Bonded Unit Count: 1
• EC Number: 216-845-5
• Exact Mass: 156.014937g/mol
• Formal Charge: 0
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Heavy Atom Count: 10
• Monoisotopic Mass: 156.014937g/mol
• NSC Number: 25408
• Rotatable Bond Count: 1