2-Phenylchinolin

830g · 2-Phenylquinoline · a-Phenylquinoline · Phenylquinoline,99% · 2-Phenylquinoline>Phenylquinoline, 99% · Quinoline, 2-phenyl- · 2-Phenylquinoline 99% · alpha-Phenylquinoline

https://huagongshe.com/de/chemical/71545

Identifikatoren & physikalische Daten

CAS No.	612-96-4
Summenformel	C15H11N
Durchschnittliche Molmasse	205,25 g/mol
Monoisotopische Masse	205,08914936 g/mol
SMILES	c1ccc(-c2ccc3ccccc3n2)cc1
InChIKey	FSEXLNMNADBYJU-UHFFFAOYSA-N
PubChem CID	71545
ChEMBL	CHEMBL89786
EC No.	210-326-7
DTXSID	DTXSID30210115
Lokaler Name	2-Phenylchinolin

Chemische & physikalische Eigenschaften

XLogP	3,9
Polarare Oberfläche (TPSA)	12,9
H-Brücken-Donoren	0
H-Brücken-Akzeptoren	1
Frei drehbare Bindungen	1
Schwere Atome	16
Formalladung	0
Komplexität	219
Kovats Retention Index	335.06339.21339.64
Schmelzpunkt	84-85 °C (lit.)
Siedepunkt	363 °C
Dichte	1.1155 (rough estimate)
Brechungsindex	1.6550 (estimate)
Lagerbedingungen	Sealed in dry,Room Temperature
pKa (Säurekonstante)	4.52±0.10(Predicted)
Aggregatzustand	Crystalline Powder
Farbe	White to light yellow
Löslichkeit	SLIGHTLY SOLUBLE
InChI	1S/C15H11N/c1-2-6-12(7-3-1)15-11-10-13-8-4-5-9-14(13)16-15/h1-11H
InChIKey	FSEXLNMNADBYJU-UHFFFAOYSA-N
SMILES	c1ccc(cc1)-c2ccc3ccccc3n2
CAS Datenbank	612-96-4(CAS DataBase Reference)
NIST chemische Informationen	Quinoline, 2-phenyl-(612-96-4)

Sicherheit & Vorschriften

GHS-Einstufung	WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (97.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard Classes and Categories	Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (97.6%)
Wassergefährdungsklasse (WGK)	3
Zollcode	29334900
R-Sätze (R)	36/37/38
Gefahrensymbole	Xi
Sicherheitshinweise (S)	26-37/39
Lagerklasse	11 - Combustible Solids
Gefahrenklasse	Eye Irrit. 2Skin Irrit. 2STOT SE 3

Anwendungen & Verwendung

Beschreibung

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.

Herstellung & Synthese

synthetische

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)