2-Phenylquinoline Chemical Properties

Melting point:

84-85 °C (lit.)

Boiling point:

363 °C

Density 

1.1155 (rough estimate)

refractive index 

1.6550 (estimate)

storage temp. 

Sealed in dry,Room Temperature

pka

4.52±0.10(Predicted)

form 

Crystalline Powder

color 

White to light yellow

Water Solubility 

SLIGHTLY SOLUBLE

λmax

258nm(lit.)

CAS DataBase Reference

612-96-4(CAS DataBase Reference)

NIST Chemistry Reference

Quinoline, 2-phenyl-(612-96-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

29334900

MSDS

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2-Phenylquinoline Usage And Synthesis

Description

2-Phenylquinoline is the major quinoline alkaloid of Galipea iongiflora, a Bolivian plant used as treatment for cutaneous leishmaniasis. Antinociceptive properties of 2-phenylquinoline isolated from the bark of Galipea iongiflora against different models of pain in mice were evaluated.

Chemical Properties

white to light yellow crystalline powder

Uses

2-Phenylquinoline was used in quantitative structure-activity relationship (QSAR) analyses of estrogen receptor β-selective ligands.

Preparation

Synthesis of 2-phenylquinoline: Quinoline (1.0 g, 7.742 mmol) and phenyl lithium (2.30 mL, 2 M, 23.22 mmol) were reacted according to general procedure. Purification of the residue by silica gel column chromatography (EtOAc:MeOH:Et3N; 10-30:1:1 or PhMe:MeOH:Et3N; 10:1:1) gave 2-phenylquinoline (0.66 g, 42%) as an orange solid.
Aniline (0.140 g, 1.50 mmol) and cinnamaldehyde (0.132 g, 1.00 mmol) were dissolved in toluene in a reaction vial equipped with a magnetic stirrer bar, followed by the addition of K10 (0.50 g). The reaction mixture was heated at a temperature of 110 ?C for 3 hours. After completion of the reaction, the crude product was purified by column chromatography over silica gel eluting with a mixture of Hexane : Ethyl acetate (20:1) to produce 2-Phenylquinoline as a yellow solid (0.044 g, 21%); (m.p. 82-84 ?C) (lit. 84-85 °C); Rf 0.67 (20:1 hexane:ethyl acetate);
1H NMR (400 MHz, CDCl3) δH 7.46-7.51 (1H, m, H-4’), 7.53-7.56 (3H, m, H-6, 3’, 5’), 7.73- 7.77 (1H, m, H-7), 7.85 (1H, d, J = 8.31 Hz, H-5), 7.88-7.91 (1H, d, J = 8.31 Hz, H-3), 8.18- 8.27 (4H, m, H-4, 8, 2’, 6’)
13C NMR(400 MHz, CDCl3) δC 119.2 (C-3), 126.7 (C-6), 127.2 (C-4a), 127.5 (C-2’, 6’), 127.9 (C-5), 128.4 (C-3’, 5’), 128.7 (C-4’), 128.9 (C-7, 8), 129.8 (C-4), 130.3 (C-1’), 137.9 (C-8a), 157.2 (C-2)

Synthesis Reference(s)

Synthetic Communications, 23, p. 1959, 1993 DOI: 10.1080/00397919308009854
Chemical and Pharmaceutical Bulletin, 26, p. 3485, 1978 DOI: 10.1248/cpb.26.3485
Journal of the American Chemical Society, 71, p. 2327, 1949 DOI: 10.1021/ja01175a017

2-Phenylquinoline(612-96-4)Related Product Information

• Isoquinoline
• 8-Hydroxyquinoline
• Quinclorac
• 4-methylquinoline
• Ethoxyquin
• 1-Phenyl-2-nitropropene
• 6-Hydroxy-2(1H)-3,4-dihydroquinolinone
• quinolinium hydrogen sulphate
• Quinhydrone
• 2-cyclopropyl-4-(4-fluorophenyl)-quinolyl-3-MethylBr
• 2-Cyclopropyl-4-(4-fluorophenyl)-quinolyl-3-methanol
• Pitavastatin calcium
• 2-Phenylquinolin-4-ol
• Ethyl 2-cyclopropyl-4-(4-fluorophenyl)-quinolyl-3-carboxylate
• 2-Cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxaldehyde
• 6,7-DIMETHOXY-1-(3,4,5-TRIETHOXYPHENYL)ISOQUINOLINE
• 3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline
• Tariquidar