530263

6-Cyano-2-naphthol

97%

• Synonym(e): 2-Cyano-6-hydroxynaphthalene, 2-Cyano-6-naphthol, 2-Hydroxy-6-naphthonitrile, 6-Cyano-2-hydroxynaphthalene, 6-Hydroxy-2-naphthalenecarbonitrile, 6-Hydroxy-2-naphthonitrile
• Lineare Formel: NCC₁₀H₆OH
• CAS-Nummer: 52927-22-7
• Molekulargewicht: 169.18
• MDL-Nummer: MFCD01863480
• UNSPSC-Code: 12352100
• PubChem Substanz-ID: 24877738
• NACRES: NA.22

Eigenschaften

• Qualitätsniveau: 100
• Assay: 97%
• mp (Schmelzpunkt): 165.5-170.5 °C (lit.)
• Funktionelle Gruppe: 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
• InChIKey: WKTNIBWKHNIPQR-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

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 pK_a^* 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]

Anwendung

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

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H315,H319,H335
• P-Sätze: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Gefahreneinstufungen: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Gloves