417548

4-Chlorophenylboronic acid

95%

• Synonym(s): (p-Chlorophenyl)boronic acid, 4-Chlorobenzeneboronic acid, NSC 25408, p-Chlorobenzeneboronic acid
• Linear Formula: ClC₆H₄B(OH)₂
• CAS Number: 1679-18-1
• Molecular Weight: 156.37
• Beilstein: 2936346
• EC Number: 216-845-5
• MDL number: MFCD00039137
• UNSPSC Code: 12352103
• PubChem Substance ID: 24866159
• NACRES: NA.22

Properties

• Assay: 95%
• mp: 284-289 °C (lit.)
• SMILES string: OB(O)c1ccc(Cl)cc1
• InChI: 1S/C6H6BClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
• InChI key: CAYQIZIAYYNFCS-UHFFFAOYSA-N

Description

Application

4-Chlorophenylboronic acid can be used as a reactant in:

• Palladium-catalyzed direct arylation.
• Cyclopalladation.
• Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation.
• Copper-mediated ligandless aerobic fluoroalkylation.
• Pd-catalyzed arylative cyclization.
• Ruthenium catalyzed direct arylation.
• Ligand-free copper-catalyzed coupling reactions.
• Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions.

It can also be used to prepare:

• Substituted diarylmethylidenefluorenes via Suzuki coupling reaction.
• Baclofen lactam by Suzuki coupling of a pyrrolinyl tosylate, followed by hydrogenation reaction.
• Palladium(II) thiocarboxamide complexes as Suzuki coupling catalysts.
• Biaryls by Suzuki reactions of aryl chlorides, bromides, and iodides with arylboronic acids.

Other Notes

Contains a varying amounts of anhydride

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Precautionary Statements: P301 + P312 + P330
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves