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:
Molecular Weight:
169.18
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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.[1] 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.[1] The proton-transfer kinetics and photophysical behavior of 6CN2 have been investigated.[2]
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[3]
- 5,7-dibromo-6-hydroxy-2-naphthonitrile[3]
- 5-chloro-6-hydroxy-2-naphthonitrile[3]
- 6-(2-imidazolyl)-2-naphthol[4]
- dodecaethylene glycol di-6-cyano-2-naphthyl ether[5]
- 6-cyano-2-naphthyl trifluoremethanesufonate[6]
- 2-(6-cyano-naphthyl)2,3,4-tri-O-acetyl-β-D-xylopyranoside[7]
- 1,5-bis(7-amidino-2-naphthalenoxy)-3-oxapentane dihydrochloride[8]
Reactant for:
- Palladium-catalyzed reduction
- Nickel-catalyzed cross-coupling reactions
- Palladium-catalyzed Heck reactions
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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Ultrafast excited-state proton transfer from cyano-substituted 2-naphthols.
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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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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
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