All Photos(4)
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:
970972
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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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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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.
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:
Phenylboronic acid may be employed as reagent in the preparation of:
- 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
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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)
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
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.
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
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