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Merck
CN

530263

6-Cyano-2-naphthol

97%

Synonym(s):

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

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About This Item

Linear Formula:
NCC10H6OH
CAS Number:
52927-22-7
Molecular Weight:
169.18
NACRES:
NA.22
PubChem Substance ID:
24877738
UNSPSC Code:
12352100
MDL number:
MFCD01863480
Assay:
97%

Key Documents

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InChI

1S/C11H7NO/c12-7-8-1-2-10-6-11(13)4-3-9(10)5-8/h1-6,13H

SMILES string

Oc1ccc2cc(ccc2c1)C#N

InChI key

WKTNIBWKHNIPQR-UHFFFAOYSA-N

assay

97%

mp

165.5-170.5 °C (lit.)

functional group

nitrile

Quality Level

100

Related Categories

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ3270
MKCQ7630
MKCJ5703
MKBT2547V
MKBR3927V

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Anna Siegbahn et al.
Organic & biomolecular chemistry, 13(11), 3351-3362 (2015-02-07)
Proteoglycans (PGs) are macromolecules that consist of long linear polysaccharides, glycosaminoglycan (GAG) chains, covalently attached to a core protein by the carbohydrate xylose. The biosynthesis of GAG chains is initiated by xylosylation of the core protein followed by galactosylation by
Ultrafast excited-state proton transfer from cyano-substituted 2-naphthols.
The Journal of Physical Chemistry A, 101(25), 4602-4605 (1997)
Doping of Polyaniline with 6-Cyano-2-naphthol.
Das D, et al.
The Journal of Physical Chemistry B, 118(45), 12993-13001 (2014)
Yong-Hong Liang et al.
Bioorganic & medicinal chemistry, 18(13), 4601-4605 (2010-06-24)
Nine newly 6-cyano-2-naphthyl substituted diarylpyrimidines (DAPY) were synthesized as non-nucleoside reverse transcriptase inhibitors on the basis of our previous work. The antiviral and cytotoxicity evaluation indicated that these compounds displayed strong activity against wild-type HIV-1 at nanomolar concentrations with selectivity
ssDNA templated assembly of oligonucleotides and bivalent naphthalene guests.
Janssen PGA, et al.
Soft Matter, 6(7), 1494-1502 (2010)
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