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Merck
CN

78181

Phenylboronic acid

purum, ≥97.0% (HPLC)

Synonym(s):

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

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About This Item

Linear Formula:
C6H5B(OH)2
CAS Number:
98-80-6
Molecular Weight:
121.93
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
329768124
EC Number:
202-701-9
Beilstein/REAXYS Number:
970972
MDL number:
MFCD00002103

Key Documents

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InChI key

HXITXNWTGFUOAU-UHFFFAOYSA-N

InChI

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

SMILES string

OB(O)c1ccccc1

grade

purum

assay

≥97.0% (HPLC)

form

crystals

mp

216-219 °C (lit.), 218-222 °C

Quality Level

200

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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.

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.

Other Notes

Contains varying amounts of phenylboronic anhydride

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7603V
WXBF4507V
WXBF1935V
WXBD9259V
WXBD2122V

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Phenylboronic-acid-based functional chemical materials for fluorescence imaging and tumor therapy
Li S, et al.
ACS Omega, 7, 2520-2532 (2022)
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)
Ni(II)-POCOP pincer compound [NiCl{C10H5-2,10-(OPPh2)2}] an efficient and robust nickel catalyst for the Suzuki-Miyaura coupling reactions
Estudiante-Negrete, F.; Hernandez-Ortega, S.; Morales-Morales, D.
Inorgorganica Chimica Acta, 387, 58-63 (2012)
A phenylboronate-functionalized polyion complex micelle for ATP-triggered release of siRNA.
Mitsuru Naito et al.
Angewandte Chemie (International ed. in English), 51(43), 10751-10755 (2012-08-22)
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)
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