Skip to Content
MilliporeSigma
All Photos(1)

Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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.)

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

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

2-Naphthol 99%

Sigma-Aldrich

185507

2-Naphthol

Doping of Polyaniline with 6-Cyano-2-naphthol.
Das D, et al.
The Journal of Physical Chemistry B, 118(45), 12993-13001 (2014)
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)
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
ssDNA templated assembly of oligonucleotides and bivalent naphthalene guests.
Janssen PGA, et al.
Soft Matter, 6(7), 1494-1502 (2010)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service