6-HYDROXY-2-NAPHTHALENEBORONIC ACID Chemical Properties

Melting point:

218-224°C

Boiling point:

458.6±37.0 °C(Predicted)

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

8.80±0.30(Predicted)

form 

powder to crystal

color 

Light yellow to Yellow to Orange

LogP

2.47 at 21.6℃

CAS DataBase Reference

173194-95-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Harmful/Irritant/Keep Cold

HS Code 

29319090

6-HYDROXY-2-NAPHTHALENEBORONIC ACID Usage And Synthesis

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

6-HYDROXY-2-NAPHTHALENEBORONIC ACID(173194-95-1)Related Product Information

• 4-Hydroxyphenylboronic acid
• 2-Hydroxyphenylboronic acid
• 4-phenylnaphthalen-1-ylboronic acid
• 6-HYDROXY-2-NAPHTHALENEBORONIC ACID
• 6-(BENZYLOXY)-2-NAPHTHYLBORONIC ACID
• 6-Ethoxy-2-naphthaleneboronic acid
• 6-METHOXY-2-NAPHTHALENEBORONIC ACID
• 6-T-BUTYLDIMETHYSILYLOXY-2-NAPHTHALENEBORONIC ACID
• 2-Naphthaleneboronic acid
• 2-(6-Benzyloxynaphthalen-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane
• 2-(6-METHOXY-2-NAPHTHYL)-5,5-DIMETHYL-1,3,2-DIOXABORINANE
• 2-(6-Methoxynaphthalen-2-yl)-4,4,6-trimethyl-1,3,2-dioxaborinane
• 6-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-2-naphthol
• 2-(6-Benzyloxynaphthalen-2-yl)-4,4,6-trimethyl-1,3,2-dioxaborinane
• 6-(TETRAHYDRO-2H-PYRAN-2-YLOXY)-2-NAPHTHYLBORONIC ACID
• 6-PENTYLOXYNAPHTHALENE-2-BORONIC ACID
• 6-(4,4,6-Trimethyl-1,3,2-dioxaborinan-2-yl)-2-naphthol