| Identification | More | [Name]
6-HYDROXY-2-NAPHTHALENEBORONIC ACID | [CAS]
173194-95-1 | [Synonyms]
6-HYDROXY-2-NAPHTHALENEBORONIC ACID
6-HYDROXY-2-NAPHTHYLENEBORONIC ACID
6-HYDROXYNAPHTHALENE-2-BORONIC ACID
AKOS BRN-0430
6-HYDROXY-2-NAPTHALENE BORONIC ACID
6-Hydroxynaphthalene-2-boronic acid 98%
6-HYDROXY-2-NAPHTALENEBORONIC ACID | [EINECS(EC#)]
687-349-8 | [Molecular Formula]
C10H9BO3 | [MDL Number]
MFCD00092986 | [Molecular Weight]
187.99 | [MOL File]
173194-95-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
218-224°C | [Boiling point ]
458.6±37.0 °C(Predicted) | [density ]
1.35±0.1 g/cm3(Predicted) | [storage temp. ]
Keep Cold | [form ]
powder to crystal | [pka]
8.80±0.30(Predicted) | [color ]
Light yellow to Yellow to Orange | [Detection Methods]
HPLC | [LogP]
2.47 at 21.6℃ | [CAS DataBase Reference]
173194-95-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [Hazard Note ]
Harmful/Irritant/Keep Cold | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
6-Hydroxynaphthalene-2-boronic acid can be used to synthesize inhibitors for oxygenase, tyrosine and phosphoinositide kinases. Tyrosine and phosphoinositide kinases are an attractive target for developing cancer drugs. | [Synthesis]
Under argon protection, 5.58 g (25 mmol) of 6-bromo-2-naphthol was dissolved in 125 mL of anhydrous tetrahydrofuran. After cooling the resulting solution to -70°C, 33 mL (55 mmol) of hexane solution of n-butyllithium was added slowly and dropwise over a period of 30 minutes. Maintaining -70°C, the reaction mixture was continued to be stirred for 1.5 hours. Subsequently, 11.5 mL (50 mmol) of triisopropyl borate was added and stirring was continued at the same temperature for 30 minutes. After that, the reaction mixture was allowed to slowly warm up to room temperature and stirred for 3 hours in the process. After completion of the reaction, 100 mL of 2 M hydrochloric acid was added to the mixture and stirred at room temperature for 2 hours. The reaction solution was separated and the aqueous phase was extracted with ethyl acetate. All organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and the solvent was subsequently evaporated. The residue was washed with dichloromethane in suspension to give 4.02 g of 6-hydroxy-2-naphthaleneboronic acid in 85% yield. | [References]
[1] Patent: EP2597094, 2013, A1. Location in patent: Paragraph 0093
[2] Patent: WO2007/68905, 2007, A1. Location in patent: Page/Page column 69-70
[3] Patent: US2004/44258, 2004, A1. Location in patent: Page 60 |
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