6-hydroxynaphthalene-2-carbonitrile

• ChemBase ID: 67669
• Molecular Formular: C11H7NO
• Molecular Mass: 169.17938
• Monoisotopic Mass: 169.05276385
• SMILES: c1c(ccc2cc(ccc12)C#N)O
• Canonical SMILES: N#Cc1ccc2c(c1)ccc(c2)O
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-hydroxynaphthalene-2-carbonitrile
• IUPAC Traditional name: 6-hydroxynaphthalene-2-carbonitrile
• Synonyms: 6-Cyano-2-naphthol; 6-Hydroxynaphthalene-2-carbonitrile; 2-Cyano-6-hydroxynaphthalene; 6-Hydroxy-2-naphthonitrile; 2-Hydroxy-6-naphthonitrile; 2-Cyano-6-naphthol; 6-Cyano-2-hydroxynaphthalene; 6-Hydroxy-2-naphthalenecarbonitrile; 6-Hydroxy-2-naphthonitrile; 6-Cyano-2-naphthol; 6-氰基-2-萘酚

Database IDs

• CAS Number: 52927-22-7
• MDL Number: MFCD01863480
• PubChem SID: 24877738; 162033404
• PubChem CID: 4589476

CALCULATED PROPERTIES

• Acid pKa: 8.926717
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.515092
• LogD (pH = 7.4): 2.502605
• Log P: 2.5152535
• Molar Refractivity: 50.2107 cm^3
• Polarizability: 20.318983 Å^3
• Polar Surface Area: 44.02 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; DMSO; Ethyl Acetate
• Apperance: Brown Solid
• Melting Point: 161-164°C; 165.5-170.5 °C(lit.); 165.5-170.5°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95+%; 97%
• Linear Formula: NCC10H6OH

DETAILS

Sigma Aldrich - 530263

Packaging
25 g in glass bottle
Application
Reactant for:
• Palladium-catalyzed reduction1
• Nickel-catalyzed cross-coupling reactions2
• Palladium-catalyzed Heck reactions3

Toronto Research Chemicals - C981980

Intermediate of Nafamostat mesilate (N210000).

REFERENCES

• Rahimian, M., et al.: Biochemistry, 48, 1573 (2009)