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78181

Sigma-Aldrich

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
Beilstein:
970972
EC Number:
202-701-9
MDL number:
MFCD00002103
UNSPSC Code:
12352103
PubChem Substance ID:
329768124
NACRES:
NA.22

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

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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
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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

JAN Code

78181-VAR:
78181-50G:
78181-RSAMPLE:
78181-BULK:
78181-1G:
78181-10G:

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD2122V
WXBD5283V
WXBD1062V
WXBC0705V
BCBL5596V

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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
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
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)
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.
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