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Phenylboronic acid

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CAS:98-80-6
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Phenylboronic acid Basic information
Product Name:Phenylboronic acid
Synonyms:phenyldihydroxyborane;t-500;usafbo-2;Benzenboronic acid;Phenylboric Acid: (Benzeneboronic acid);Phenylboronic acid, May contain varying amounts of anhydride, 97%;Phenylboronic acid, may contain varying amounts of anhydride, 98+%;phenylboronic acid(SALTDATA: H2O)
CAS:98-80-6
MF:C6H7BO2
MW:121.93
EINECS:202-701-9
Product Categories:Aryl Boronic Acids;Boronic Acids and Derivatives;Chemical Synthesis;Organometallic Reagents;Unsubstituted Aryl Boronic Acids;OLED materials,pharm chemical,electronic;Aryl;Organoborons;Analytical Chemistry;B (Classes of Boron Compounds);Boronic Acid, etc. (GC Derivatizing Reagents);Boronic Acids;Boronate Ester;Potassium Trifluoroborate;Boron compounds;blocks;BoronicAcids;Boronic Acid series;PHARMACEUTICAL INTERMEDIATES;Substituted Boronic Acids;Organometallics;Boronic Acid;GC Derivatizing Reagents;organic or inorganic borate;bc0001;98-80-6
Mol File:98-80-6.mol
Phenylboronic acid Structure
Phenylboronic acid Chemical Properties
Melting point 216-219 °C(lit.)
Boiling point 265.9±23.0 °C(Predicted)
density 1.13±0.1 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form Crystalline Powder
pka8.83(at 25℃)
color White to off-white
Water Solubility 10 g/L (20 ºC)
Sensitive Hygroscopic
Merck 14,1068
BRN 970972
Stability:Hygroscopic
InChI1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H
InChIKeyHXITXNWTGFUOAU-UHFFFAOYSA-N
SMILESOB(O)c1ccccc1
CAS DataBase Reference98-80-6(CAS DataBase Reference)
EPA Substance Registry SystemBoronic acid, phenyl- (98-80-6)
Safety Information
Hazard Codes Xn,Xi,N
Risk Statements 22-36/37/38-20/21/22
Safety Statements 22-24/25-36/37/39-26-36
WGK Germany 3
RTECS CY8575000
Hazard Note Harmful
TSCA TSCA listed
HazardClass IRRITANT, MOISTURE SENSITIVE
HS Code 29310095
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
ToxicityLD50 orl-rat: 740 mg/kg 14KTAK -,693,64
MSDS Information
ProviderLanguage
Benzeneboronic acid English
SigmaAldrich English
ACROS English
ALFA English
Phenylboronic acid Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powder. Insoluble in water and benzene, easily soluble in ether and methanol. When exposed to air or under heating conditions, it is easy to dehydrate and form a three-molecular polymer.
UsesPhenylboronic Acid is a compound used in organic synthesis of various pharmaceutical goods.
Phenylboronic acid (PBA) and its derivatives can bind sugars and other diol compounds to form cyclic boronate esters. These esters bear negative charges. Due to this reaction, sugars can be detected by means of electrochemical and optical techniques.
PBA modified electrodes have been constructed as reagentless electrochemical sensors. There, PBA is absorbed on the electrode surface either as a self- assembled monolayer film ore a polymer thin film. Basically, for optical detection techniques for the detection of sugars, PBA is modified with a chromophore that should change its properties on reaction with a sugar.
Reaction of Phenylboronic acid with a sugar
Reaction of Phenylboronic acid with a sugar
Characteristics Phenylboronic acid and its derivatives form complexes with polyol compounds such as saccharides and poly(vinyl alcohol) (PVA). Glucose-sensitive hydrogels can be prepared by using phenylhoronic acid as a ligand for target glucose. For example. a copolymer with phenylboronic acid moieties was synthesized by copolymerization of 4V-vinyl-2-pyrrolidone (NVP) and 3-(acryl- amide)phcnylhoronic acid (PBA). The complexes between the NVP-PBA copolymer and PVA enable us to construct glucose-sensitive insulin release systems because the complexes dissociated in response to the glucose concentration.
This phenylboronic acid is soluble in water and the coupling reaction can even be carried out in water. It is compatible with many organic substituents such as esters, ketones, alcohols, etc. which would prohibit the use of Grignard reagents in coupling reactions.
ApplicationDue to its good water solubility and low cytotoxicity, Phenylboronic acid is used as a potential nuclear-targeted boron agent for neutron capture therapy of melanoma. Phenylboronic acid was found to have a boron concentration of 74.47 ± 12.17 ng/106 cells in B16F10 cells and 45.77 ± 5.64 ng/106 cells in the nucleus.[1]
DefinitionChEBI: Phenylboronic acid is a member of boronic acids. It is functionally related to a boronic acid.
Synthesis Reference(s)Organic Syntheses, Coll. Vol. 4, p. 68, 1963
The Journal of Organic Chemistry, 49, p. 5237, 1984 DOI: 10.1021/jo00200a045
General DescriptionPhenylboronic 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.
Safety ProfilePoison by intravenous andintraperitoneal routes. Moderately toxic by ingestion.Mildly toxic by skin contact. When heated to decomposition it emitsacrid smoke and irritating fumes.
Toxicity evaluationAcute toxicity studies with Phenylboronic acid have shown that Rat has an oral LD50 of 740 mg/kg. it is harmful if swallowed and may be irritating to the skin, eyes and respiratory tract.
References[1] CHEN J, LI Y, GAN X, et al. Unlocking the potential: phenylboronic acid as a nuclear-targeting boron agent for neutron capture therapy[J]. Medical Oncology, 2024, 1110 1. DOI:10.1007/s12032-024-02351-3.
Tag:Phenylboronic acid(98-80-6) Related Product Information
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