612-96-4

Basic information

• Product Name: 2-Phenylquinoline
• Synonyms: alpha-Phenylquinoline;2-Phenylquinoline, 99+%;Phenylquinoline,99%;a-Phenylquinoline;2-Phenylquinoline;Phenylquinoline, 99%;2-Phenylquinoline, 99+% 1GR;2-Phenylquinoline 99%
• CAS NO: 612-96-4
• Molecular Formula: C₁₅H₁₁N
• Molecular Weight: 205.25
• EINECS: 210-326-7
• Product Categories: Quinolines, Quinazolines and derivatives;API intermediates;Building Blocks;Heterocyclic Building Blocks;Quinolines
• Mol File: 612-96-4.mol
• Article Data: 448

Chemical Properties

• Melting Point: 84-85 °C(lit.)
• Boiling Point: 363 °C
• Flash Point: 159.1°C
• Appearance: White to light yellow/Crystalline Powder
• Density: 1.1155 (rough estimate)
• Vapor Pressure: 3.89E-05mmHg at 25°C
• Refractive Index: 1.6550 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.52±0.10(Predicted)
• Water Solubility: SLIGHTLY SOLUBLE
• CAS DataBase Reference: 2-Phenylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenylquinoline(612-96-4)
• EPA Substance Registry System: 2-Phenylquinoline(612-96-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 612-96-4(Hazardous Substances Data)

Usage

Description

2-Phenylquinoline is the major quinoline alkaloid of Galipea iongiflora, a Bolivian plant used as treatment for cutaneous leishmaniasis. It possesses antinociceptive properties and has been evaluated for its efficacy against different models of pain in mice.
Used in Pharmaceutical Industry:
2-Phenylquinoline is used as a potential therapeutic agent for the treatment of cutaneous leishmaniasis, a parasitic disease caused by Leishmania species.
Used in Pain Management:
2-Phenylquinoline is used as an antinociceptive agent for the management of pain in various models, demonstrating its potential as a pain-relieving compound.
Used in Drug Design and Development:
2-Phenylquinoline is used as a reference compound in quantitative structure-activity relationship (QSAR) analyses for the development of estrogen receptor β-selective ligands, contributing to the advancement of drug design and discovery.

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

InChI:InChI=1/C15H11N/c1-2-6-12(7-3-1)15-11-10-13-8-4-5-9-14(13)16-15/h1-11H

Upstream product

• 1613-37-2 Quinoline N-oxide 
• 60-29-7 diethyl ether 
• 71-43-2 benzene 
• 4979-79-7 4-chloro-2-phenylquinoline 
• 40515-82-0 2-(2-quinolinyl)phenol 
• 62961-62-0 (Z)-3-hydroxy-1,3-diphenyl-2-propen-1-one 
• 529-23-7 o-aminobenzaldehyde 
• 120-46-7 1,3-diphenylpropanedione 
• 64-17-5 ethanol 
• 98-86-2 acetophenone 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 123-63-7 paracetaldehyde 
• 612-62-4 2-Chloroquinoline 
• 98-80-6 phenylboronic acid 

Downstream Products

• 119408-46-7 2-(quinolin-2-yl)phenyltellurium(II) bromide 
• 119408-50-3 dimethyldithiocarbamato<2-(quinolin-2-yl)phenyl>tellurium(II) 
• 1236385-05-9 4-chloro-2-phenyl-1,2-dihydroquinoline-1,3-dicarbaldehyde 
• 100965-25-1 2-(2-chlorophenyl)quinoline 
• 1662702-42-2 8-(2-chlorobenzoyl)-2-phenylquinoline 
• 1662702-46-6 2-phenyl-11H-indeno[1,2-h]quinolin-11-one 
• 1662702-32-0 8-iodo-2-phenylquinoline 
• 1584673-28-8 2-(2-(phenylthio)phenyl)quinoline 
• 5278-56-8 2-(o-nitrophenyl)quinoline 

Relevant articles and documents

Substrate-Tuned Domino Annulation for Selective Synthesis of Poly-substituted Benzo[ f]imidazo[2,1- a][2,7]naphthyridines and 3-Azaheterocyclic Substituted 2-Arylquinolines

A domino annulation/oxidation of heterocyclic ketene aminals (HKAs) and 2-aminochalcones has been developed for the selective synthesis of poly-substituted benzo[f]imidazo[2,1-a][2,7]naphthyridines and 3-azaheterocyclic substituted 2-arylquinolines. These reactions proceed well under mild conditions without any additives. Plausible mechanisms for such a polycyclic ring system assembly were also proposed. Moreover, benzo[f]imidazo[2,1-a][2,7]naphthyridine 3g displayed a fluorescence effect, demonstrating the potential applications in organic optical materials.

Furfuryl vinyl ethers in [4+2]-cycloaddition reactions

For the first time [4+2]-cycloaddition reactions were carried out between furfuryl vinyl ethers and typical dienophiles and heterodienes proceeding in uncatalyzed conditions and resulting in previously unknown heterocyclic systems containing either free v

Dehydrogenation of N-Heterocyclic Compounds Using H2O2 and Mediated by Polar Solvents

The oxidative dehydrogenation of N-heterocyclic compounds by using H2O2 as oxidant in combination with polar solvents such as 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and H2O is described. Among these two solvents, the best yields for the heteroaromatic compounds were generally achieved in HFIP. However, it is remarkable, that the use of a non toxic solvent such as H2O gave such good yields. Furthermore, the procedure was implemented in larger-scale and HFIP was distilled from the reaction mixture and reused (up to 5 cycles) without a significant detriment in the reaction outcome. (Figure presented.).

Iron catalyzed metal-ligand cooperative approaches towards sustainable synthesis of quinolines and quinazolin-4(3H)-ones

Herein we report simple, efficient, and economically affordable metal-ligand cooperative strategies for synthesizing quinolines and quinazolin-4(3H)-ones via dehydrogenative functionalization of alcohols. Various polysubstituted quinolines and quinazolin-4(3H)-ones were prepared in good yields via dehydrogenative coupling of readily available alcohols with ketones and 2-aminobenzamides, respectively under air using a well-defined Fe(II)-catalyst, ([FeL1Cl2] (1)) bearing a redox-active azo-aromatic pincer 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline) (L1). Control experiments and mechanistic investigation disclose that the one-electron reduced mono-anionic species [1]? bearing an iron-stabilized azo-anion radical ligand catalyzes these reactions. Both iron and the redox-active arylazo ligand participate synergistically during the different steps of these catalytic reactions.