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78181

Sigma-Aldrich

Phenylboronic acid

purum, ≥97.0% (HPLC)

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Synonym(s):
Benzeneboronic acid, Dihydroxyphenylborane, NSC 66487, Phenyl-boric acid, Phenylboric acid, Phenyldihydroxyborane
Linear Formula:
C6H5B(OH)2
CAS Number:
Molecular Weight:
121.93
Beilstein/REAXYS Number:
970972
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

grade

purum

Quality Level

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

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1 of 4

This Item
P20009524018647098
vibrant-m

78181

Phenylboronic acid

vibrant-m

P20009

Phenylboronic acid

vibrant-m

524018

4-Mercaptophenylboronic acid

vibrant-m

647098

Phenylboronic acid pinacol ester

mp

216-219 °C (lit.), 218-222 °C

mp

216-219 °C (lit.)

mp

>230 °C (lit.)

mp

27-31 °C (lit.)

form

crystals

form

crystals

form

solid

form

solid

grade

purum

grade

-

grade

-

grade

-

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

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

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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)
Peng-Cheng Chen et al.
Langmuir : the ACS journal of surfaces and colloids, 27(20), 12597-12605 (2011-09-09)
Phenylboronic acid (PBA)-functionalized materials have attracted considerable attention because of their potential applications in many fields. In this paper, we report a PBA-segregated honeycomb-patterned porous film (HPPF) for glucose sensing. Polystyrene-block-poly(acrylic acid-co-acrylamidophenylboronic acid) with different contents of PBA pendants was
Riina K Arvela et al.
Organic letters, 7(11), 2101-2104 (2005-05-20)
[reaction: see text]. We present here a methodology for the Suzuki coupling of aryl chlorides with phenylboronic acid using Pd/C as a catalyst, water as a solvent, and microwave heating. We show that simultaneous cooling in conjunction with microwave heating
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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