Synthesis
In a 5000 mL three-necked flask, add 350 g of 6-hydroxy-2-naphthaldehyde (2.0 mol), 278 g of hydroxylamine hydrochloride (4.0 mol), and 3500 mL of dimethyl sulfoxide. Stir and heat to 100 °C, maintain the reaction temperature for 1 hour, then cool to room temperature. Mix the reaction solution with a large amount of water, and precipitate a solid with stirring. Filter, wash the filter cake with water to obtain a wet crude product, which is directly recrystallized from ethanol/water solution to give 237 g of a grayish-white purified product, yield 70%.
Chemical Properties
Brown Crystalline Solid. 6-Cyano-b-naphthol [52927-22-7], 6-cyano2-hydroxynaphthalene, 6-hydroxy-2-naphthoic acid nitrile, Mr 169.17, mp 166 – 167℃ This nitrile is used as an intermediate for the production of liquid crystals and monoamino-oxidase-inhibiting naphthalene-2-oxyalkylamines, which are used as antidepressive agents.
Uses
Intermediate of Nafamostat mesilate (N210000).
Uses
Reactant for:
- Palladium-catalyzed reduction
- Nickel-catalyzed cross-coupling reactions
- Palladium-catalyzed Heck reactions
General Description
6-Cyano-2-naphthol (6CN2) is an aromatic alcohol that can be synthesized from 6-bromo-2-naphthol. It is a superphotoacid with the ground state p
Ka* value of 8.4 and excited state p
Kavalue of 0.2, respectively. 6CN2 protonates PANI-ES (polyaniline emeraldine salt) to form PANI-EB (emeraldine base), which shows enhanced conductivity. The proton-transfer kinetics and photophysical behavior of 6CN2 have been investigated.
