Phenylboronic Acid
PhB(OH)2 · BENZENEBORONIC ACID · PHENYLBORIC ACID · phenyboronic · phenyldihydroxyborane · CAS:98-80-6 · phenyl-boronicaci · Phenylboranic acid
Identifiers & Physical Properties
| CAS No. | 98-80-6 |
|---|---|
| Molecular formula | C6H7BO2 |
| Average molar mass | 121.93 g/mol |
| Monoisotopic mass | 122.0539096 g/mol |
| SMILES | OB(O)c1ccccc1 |
| InChIKey | HXITXNWTGFUOAU-UHFFFAOYSA-N |
| PubChem CID | 66827 |
| ChEMBL | CHEMBL21485 |
| ChEBI | CHEBI:44923 |
| EC No. | 202-701-9 |
| DTXSID | DTXSID9059179 |
Chemical & Physical Properties
| Topological polar surface area | 40.5 |
|---|---|
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 1 |
| Heavy atoms | 9 |
| Formal charge | 0 |
| Complexity | 79 |
| Boiling point | 219 °C @760 [mm Hg]265.9±23.0 °C(Predicted) |
| Vapor pressure | 0.00000856 [mmHg] |
| Physical Description | Solid[Merck Index] White to off-white hygroscopic solid[Acros Organics MSDS] |
| Melting point | 216-219 °C(lit.) |
| Density | 1.13±0.1 g/cm3(Predicted) |
| Storage conditions | Keep in dark place,Sealed in dry,Room Temperature |
| Solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)10 g/L (20 ºC) |
| Physical state | Crystalline Powder |
| pKa (acidity coefficient) | 8.83(at 25℃) |
| Color | White to off-white |
| Sensitivity | Hygroscopic |
| Merck | 14,1068 |
| BRN | 970972 |
| Stability | Hygroscopic |
| InChI | 1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H |
| InChIKey | HXITXNWTGFUOAU-UHFFFAOYSA-N |
| SMILES | OB(O)c1ccccc1 |
| CAS DataBase Reference | 98-80-6(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | L12H7B02G5 |
| EPA Substance Registry System | Boronic acid, phenyl- (98-80-6) |
| UNSPSC Code | 12352103 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302 |
| GHS precautionary statements | P264-P270-P301+P312-P501 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xn,Xi,N |
| Risk statements (R) | 22-36/37/38-20/21/22 |
| Safety statements (S) | 22-24/25-36/37/39-26-36 |
| Water hazard class (WGK) | 3 |
| RTECS number | CY8575000 |
| Hazard Note | Harmful |
| TSCA inventory status | TSCA listed |
| Hazard class | IRRITANT, MOISTURE SENSITIVEAcute Tox. 4 Oral |
| Customs code | 29310095 |
| Storage class | 11 - Combustible Solids |
| Toxicity | LD50 orl-rat: 740 mg/kg 14KTAK -,693,64 |
Safety & Regulations
| GHS classification | WarningH302 (96.6%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 208 reports by companies from 17 notifications to the ECHA C&L Inventory.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Chemical: Boronic acid, phenyl-Benzeneboronic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | Spontaneously converts to benzene boronic anhydride (C6-H5-B-O) in dry air[Merck Index] An irritantHarmful by ingestion[Acros Organics MSDS] See Boron. |
| Hazard Classes and Categories | Acute Tox. 4 (96.6%) |
| Protective Action Criteria (PAC) | 2.2 [mg/m3]24 [mg/m3]150 [mg/m3] |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | CY8575000 |
| Customs code | 29310095 |
| Toxicity | LD50 orl-rat: 740 mg/kg 14KTAK -,693,64 |
| Risk statements (R) | 22-36/37/38-20/21/22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn,Xi,N |
| hazard_note | Harmful |
| Safety statements (S) | 22-24/25-36/37/39-26-36 |
| Hazard class | IRRITANT, MOISTURE SENSITIVEAcute Tox. 4 Oral |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H302 |
| GHS precautionary statements | P264-P270-P301+P312-P501 |
Applications & Uses
Uses
Phenylboronic 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
General Description
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.