2-phenylquinoline-4-carboxylic acid

• ChemBase ID: 107478
• Molecular Formular: C16H11NO2
• Molecular Mass: 249.26404
• Monoisotopic Mass: 249.0789786
• SMILES: OC(=O)c1cc(nc2ccccc12)c1ccccc1
• Canonical SMILES: OC(=O)c1cc(nc2c1cccc2)c1ccccc1
• InChI: InChI=1S/C16H11NO2/c18-16(19)13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10H,(H,18,19)
• InChIKey: YTRMTPPVNRALON-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-phenylquinoline-4-carboxylic acid
• IUPAC Traditional name: tervalon; 2-phenylquinoline-4-carboxylic acid
• Synonyms: CINCHOPHEN; 2-Phenylcinchoninic acid; Cinchophen; 2-Phenyl-4-quinolinecarboxylic acid; 2-Phenylquinoline-4-carboxylic acid; 2-phenylquinoline-4-carboxylic acid; Atophan; Quinophen; Aciphenoquinoline; Cincophen; Cinchophen; 2-苯辛可宁酸; 辛可芬; 2-苯基-4-喹啉羧酸

Database IDs

• CAS Number: 132-60-5
• EC Number: 205-067-1
• MDL Number: MFCD00006750
• Beilstein Number: 192803
• Merck Index: 142288
• PubChem SID: 162095093; 24851762
• PubChem CID: 8593

CALCULATED PROPERTIES

• Acid pKa: 3.5717108
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.8889003
• LogD (pH = 7.4): 0.46544552
• Log P: 3.821559
• Molar Refractivity: 71.9997 cm^3
• Polarizability: 30.321333 Å^3
• Polar Surface Area: 50.19 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Insoluble in water
• Melting Point: 212-218°C; 214-215 °C(lit.); 214-215°C

Safety Information

• Storage Warning: Light Sensitive
• RTECS: GD4025000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301; H302
• GHS Precautionary statements: P264-P270-P301+P310-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: Others
• Mechanism of Action: Uricosuric

Product Information

• Purity: 99%
• Salt Data: Free Base
• Application(s): Analgesic; Antigout; Antiinflammatory agent; Antirheumatic
• Empirical Formula (Hill Notation): C16H11NO2

DETAILS

Sigma Aldrich - 196479

Packaging
50 g in glass bottle

REFERENCES

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 871A, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 449C; 450C, (nmr)
• Doebner, O. et al., Annalen, 1887, 242, 290, (synth)
• Pfitzinger, W., J. Prakt. Chem., 1897, 56, 293, (synth)
• U.S. Pat., 1920, 1 336 952; CA, 14, 1736, (deriv)
• Rosenmund, K.W., Ber., 1921, 54, 2893, (deriv)
• Du Puis, R.N. et al., J.A.C.S., 1934, 56, 471
• Poluektov, N.S. et al., Zh. Anal. Khim., 1972, 27, 266, (detn, rare earths)
• Belt'yukova, S.V., Zh. Anal. Khim., 1975, 30, 1321, (detn, Sc)
• Ozawa, F. et al., J.O.C., 1986, 51, 415, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 5813
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 10
• Blackburn, A.C. et al., Acta Cryst. C, 1996, 52, 409-411, (cryst struct)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PGG000