78181
Phenylboronic acid
purum, ≥97.0% (HPLC)
Sinónimos:
Benzeneboronic acid, Dihydroxyphenylborane, NSC 66487, Phenyl-boric acid, Phenylboric acid, Phenyldihydroxyborane
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Fórmula lineal:
C6H5B(OH)2
Número CAS:
Peso molecular:
121.93
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
EC Number:
202-701-9
Beilstein/REAXYS Number:
970972
MDL number:
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Permítanos ayudarleInChI 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
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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
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Clase de almacenamiento
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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Journal of the American Oil Chemists' Society, 75(11), 1545-1549 (1998)
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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.
Tobias Müller et al.
Chemical communications (Cambridge, England), 49(4), 361-363 (2012-11-30)
The base is a key factor in aldol reactions in organic media, determining the selectivity. Here, we describe a tetrahedral phenylboronate salt as a mild non-nucleophilic base that is able to catalyse the aldol reaction and significantly decrease the formation
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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