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530263 Sigma-Aldrich

6-Cyano-2-naphthol

97%

Synonym: 2-Cyano-6-hydroxynaphthalene, 2-Hydroxy-6-naphthonitrile, 2-Cyano-6-naphthol, 6-Cyano-2-hydroxynaphthalene, 6-Hydroxy-2-naphthalenecarbonitrile, 6-Hydroxy-2-naphthonitrile

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Properties

Related Categories Building Blocks, C10 to C27, Chemical Synthesis, Cyanides/Nitriles, Nitrogen Compounds - Organic Building Blocks,
Quality Level   100
assay   97%
mp   165.5-170.5 °C (lit.)
SMILES string   Oc1ccc2cc(ccc2c1)C#N
InChI   1S/C11H7NO/c12-7-8-1-2-10-6-11(13)4-3-9(10)5-8/h1-6,13H
InChI key   WKTNIBWKHNIPQR-UHFFFAOYSA-N

Description

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 pKa* value of 8.4 and excited state pKavalue 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.

Application

6-Cyano-2-naphthol (6-Hydroxy-2-naphthonitrile, 2-cyano-6-naphthol) may be used in the preparation of:
• 5-bromo-6-hydroxy-2-naphthonitrile
• 5,7-dibromo-6-hydroxy-2-naphthonitrile
• 5-chloro-6-hydroxy-2-naphthonitrile
• 6-(2-imidazolyl)-2-naphthol
• dodecaethylene glycol di-6-cyano-2-naphthyl ether
• 6-cyano-2-naphthyl trifluoremethanesufonate
• 2-(6-cyano-naphthyl)2,3,4-tri-O-acetyl-β-D-xylopyranoside
• 1,5-bis(7-amidino-2-naphthalenoxy)-3-oxapentane dihydrochloride

Reactant for:
• Palladium-catalyzed reduction
• Nickel-catalyzed cross-coupling reactions
• Palladium-catalyzed Heck reactions

Packaging

25 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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