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530263

Sigma-Aldrich

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
MDL number:
MFCD01863480
UNSPSC Code:
12352100
PubChem Substance ID:
24877738
NACRES:
NA.22

Quality Level

100

Assay

97%

mp

165.5-170.5 °C (lit.)

functional group

nitrile

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

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

JAN Code

530263-25G:4548173166735
530263-VAR:
530263-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ7630
MKCJ5703
MKBT2547V
MKBR3927V
MKBH5434V

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2-Naphthol 99%

Sigma-Aldrich

185507

2-Naphthol

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
Doping of Polyaniline with 6-Cyano-2-naphthol.
Das D, et al.
The Journal of Physical Chemistry B, 118(45), 12993-13001 (2014)
Ultrafast excited-state proton transfer from cyano-substituted 2-naphthols.
The Journal of Physical Chemistry A, 101(25), 4602-4605 (1997)
T Nakayama et al.
Chemical & pharmaceutical bulletin, 41(1), 117-125 (1993-01-01)
By developing 6-amidino-2-naphthyl 4-guanidinobenzoate (I, FUT-175) as a basic structure, its various derivatives were synthesized and their inhibitory activities on trypsin, plasmin, kallikrein, thrombin, C1r and C1s as well as on complement-mediated hemolysis were examined. The protective effect of these
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
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