Benzeneboronic Acid
Product Information
Molecular Formula
C6H7O2B
Molecular Weight
121.93
Description
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.
Synonyms
phenylboronic acid; phenylboronic acid
IUPAC Name
phenylboronic acid
SMILES
B(C1=CC=CC=C1)(O)O
InChI
InChI=1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H
InChI Key
HXITXNWTGFUOAU-UHFFFAOYSA-N
Boiling Point
265.9 °C at 760 mmHg
Melting Point
216-219 °C (lit.)
Flash Point
Not applicable
Purity
≥ 97.0 % (HPLC)
Density
1.13 g/cm3
Appearance
Solid
LogP
-0.63360
Vapor Pressure
0.00000856 [mmHg]
Safety Information
Hazards
H302
Precautionary Statement
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501
Signal Word
Warning
Computed Properties
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
122.0539096 g/mol
Monoisotopic Mass
122.0539096 g/mol
Topological Polar Surface Area
40.5Ų
Heavy Atom Count
9
Formal Charge
0
Complexity
79.1
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| US-2016272588-A1 | Usp7 inhibitor compounds and methods of use | 2015-03-20 |
| US-2016264518-A1 | Alpha-cinnamide compounds and compositions as hdac8 inhibitors | 2015-03-13 |
| US-2016257633-A1 | Processes for preparing (r)-1-(5-chloro-[1,1`-biphenyl]-2-yl)-2,2,2-trifluoroethanol and 1-(5-chloro-[1,1`-biphenyl]-2-yl)-2,2,2-trifluoroethanone | 2015-03-05 |
| US-2016251361-A1 | Imidazopyrimidine and imidazotriazine derivative, and pharmaceutical composition comprising the same | 2015-02-26 |
| US-2016244449-A1 | Bicyclic heterocycles as fgfr4 inhibitors | 2015-02-20 |
| US-2016240783-A1 | Indenotriphenylene-based amine derivative for organic electroluminescent device | 2015-02-17 |
| US-2016229833-A1 | Quinazolinones and azaquinazolinones as ubiquitin-specific protease 7 inhibitors | 2015-02-05 |
| US-2016229872-A1 | Isothiazolopyrimidinones, pyrazolopyrimidinones, and pyrrolopyrimidinones as ubiquitin-specific protease 7 inhibitors | 2015-02-05 |
| US-2016221972-A1 | 3-alkyl bicyclic [4,5,0] hydroxamic acids as hdac inhibitors | 2015-02-02 |
| US-2016221973-A1 | 3-aryl bicyclic [4,5,0] hydroxamic acids as hdac inhibitors | 2015-02-02 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 26025252 | 2015-05-01 | Phenylboronic Acid Solid Phase Extraction Cleanup and Isotope Dilution Liquid Chromatography-Tandem Mass Spectrometry for the Determination of Florfenicol Amine in Fish Muscles | Journal of AOAC International |
| 22796889 | 2012-11-01 | Emergence of NDM-1- and IMP-14a-producing Enterobacteriaceae in Thailand | The Journal of antimicrobial chemotherapy |
| 22978786 | 2012-10-24 | A structure-function relationship for the optical modulation of phenyl boronic acid-grafted, polyethylene glycol-wrapped single-walled carbon nanotubes | Journal of the American Chemical Society |
| 22907668 | 2012-10-22 | A phenylboronate-functionalized polyion complex micelle for ATP-triggered release of siRNA | Angewandte Chemie (International ed. in English) |
| 22957842 | 2012-10-08 | Phenylboronic acid-based complex micelles with enhanced glucose-responsiveness at physiological pH by complexation with glycopolymer | Biomacromolecules |
| 22930528 | 2012-09-17 | A mechanically controlled indicator displacement assay | Angewandte Chemie (International ed. in English) |
| 22835873 | 2012-09-01 | Anion inhibition studies of an α-carbonic anhydrase from the thermophilic bacterium Sulfurihydrogenibium yellowstonense YO3AOP1 | Bioorganic & medicinal chemistry letters |
| 22517671 | 2012-07-01 | Phenylboronic-acid-modified amphiphilic polyether as a neutral gene vector | Macromolecular bioscience |
| 22951650 | 2012-07-01 | [Detection of plasmid-mediated AmpC beta-lactamase in clinical isolates of cefoxitin-resistant Escherichia coli and Klebsiella pneumoniae] | Mikrobiyoloji bulteni |
| 23032831 | 2012-07-01 | Phenotypic method for differentiation of carbapenemases in Enterobacteriaceae: study from north India | Indian journal of pathology & microbiology |
