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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

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

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

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’.

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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)
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