78181

Phenylboronic acid

purum, ≥97.0% (HPLC)

• Synonym(s): Benzeneboronic acid, Dihydroxyphenylborane, NSC 66487, Phenyl-boric acid, Phenylboric acid, Phenyldihydroxyborane
• Linear Formula: C₆H₅B(OH)₂
• CAS Number: 98-80-6
• Molecular Weight: 121.93
• Beilstein: 970972
• EC Number: 202-701-9
• MDL number: MFCD00002103
• UNSPSC Code: 12352103
• PubChem Substance ID: 329768124
• NACRES: NA.22

Properties

• grade: purum
• Quality Level: 200
• Assay: ≥97.0% (HPLC)
• form: crystals
• mp: 216-219 °C (lit.); 218-222 °C
• SMILES string: OB(O)c1ccccc1
• InChI: 1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H
• InChI key: HXITXNWTGFUOAU-UHFFFAOYSA-N

Description

General description

Phenylboronic acid is a highly stable receptor ligand used in cross-coupling reactions and drug delivery.

Phenylboronic acid (PBA) is an organoboronic acid. It behaves as a molecular receptor that can attach to compounds containing cis-diol group. Microwave-assisted Suzuki coupling of aryl chlorides with phenylboronic acid in the presence of Pd/C (catalyst) and water (solvent) has been described. Palladium-catalyzed cross-coupling reaction of phenylboronicacid with haloarenes to afford biaryls has been reported.

Application

Phenylboronic acid may be employed in the following reactions:

• Rhodium-catalyzed intramolecular amination.
• Pd-catalyzed direct arylation.
• Mizoroki-Heck and Suzuki-Miyaura coupling reactions catalyzed by palladium nanoparticles.
• Palladium-catalyzed stereoselective Heck-type reaction.
• Highly effective Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water.

Phenylboronic acid may be employed as reagent in the preparation of:

• Ni(II) pincer complex and Pd(II) pyridoxal hydrazone metallacycles as catalysts for the Suzuki-Miyaura cross-coupling reactions.
• N-type polymers for all-polymer solar cells.
• Novel series of potent and selective mTOR kinase inhibitors.
• Inhibitors of lactate dehydrogenase against cancer cell proliferation.

Other Notes

Contains varying amounts of phenylboronic anhydride

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Precautionary Statements: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves