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Sigma-Aldrich

Phenylboronic acid

purum, ≥97.0% (HPLC)

Synonyme(s) :

Benzeneboronic acid, Dihydroxyphenylborane, NSC 66487, Phenyl-boric acid, Phenylboric acid, Phenyldihydroxyborane

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About This Item

Formule linéaire :
C6H5B(OH)2
Numéro CAS:
98-80-6
Poids moléculaire :
121.93
Numéro Beilstein :
970972
Numéro CE :
202-701-9
Numéro MDL:
MFCD00002103
Code UNSPSC :
12352103
ID de substance PubChem :
329768124
Nomenclature NACRES :
NA.22

Qualité

purum

Niveau de qualité

200

Pureté

≥97.0% (HPLC)

Forme

crystals

Pf

216-219 °C (lit.)
218-222 °C

Chaîne SMILES 

OB(O)c1ccccc1

InChI

1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H

Clé InChI

HXITXNWTGFUOAU-UHFFFAOYSA-N

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Description générale

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.

Autres remarques

Contains varying amounts of phenylboronic anhydride

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
WXBF4507V
WXBF1935V
WXBD9259V
WXBD2122V
WXBD5283V

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Consulter la Bibliothèque de documents

Synthesis of polyfunctional glycerol esters: lipase-catalyzed esterification of glycerol with diesters.
Villeneuve P, et al.
Journal of the American Oil Chemists' Society, 75(11), 1545-1549 (1998)
Phenylboronic-acid-based functional chemical materials for fluorescence imaging and tumor therapy
Li S, et al.
ACS Omega, 7, 2520-2532 (2022)
Discovery and SAR exploration of a novel series of imidazo[4,5-b]pyrazin-2-ones as potent and selective mTOR kinase inhibitors
Mortensen, D. S.; et al.
Bioorganic & Medicinal Chemistry, 21, 6793-6799 (2011)
María Moreno-Guzmán et al.
Biosensors & bioelectronics, 35(1), 82-86 (2012-03-14)
This work reports for the first time an electrochemical immunosensor for the determination of adrenocorticotropin hormone (ACTH). The immunoelectrode design involves the use of amino phenylboronic acid for the oriented immobilization of anti-ACTH antibodies onto screen-printed carbon modified electrode surfaces.
Erjun Zhou et al.
Chemical communications (Cambridge, England), 48(43), 5283-5285 (2012-04-24)
A new alternating copolymer of fluorene and naphthalene diimide, PF-NDI, was synthesized and characterized. The highest power conversion efficiency of all-polymer solar cells based on P3HT:PF-NDI reached 1.63% with a relatively high fill factor of 0.66 by using 1,8-diiodooctane as
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