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. 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: 10.1080/00397919308009854Chemical 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

• 123-91-1 1,4-dioxane 
• 91-22-5 quinoline 
• 60-29-7 diethyl ether 
• 110-86-1 pyridine 
• 108-86-1 bromobenzene 
• 612-62-4 2-Chloroquinoline 
• 1613-37-2 Quinoline N-oxide 
• 71-43-2 benzene 
• 10285-99-1 2-methoxyquinoline N-oxide 
• 1144-20-3 2-phenyl-4-quinolinol 
• 887-94-5 1-methyl-2-phenyl-1,2-dihydroquinoline 
• 53744-31-3 2-nitrochalcone 
• 37056-75-0 cinnamaldehyde-(N-phenyl oxime ) 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 5659-33-6 2-phenylquinoline 1-oxide 
• 2973-26-4 2-phenyl-4-quinolinecarbonitrile 
• 24005-23-0 2-phenyl-1,2,3,4-tetrahydroquinoline 
• 55570-28-0 2,2-Diphenyl-1,2-dihydrochinolin 
• 14886-84-1 N-methyl-2-phenylquinolium iodide 
• 579-93-1 2-(Benzoylamino)benzoic Acid 
• 1570-04-3 2-phenyl-5,6,7,8-tetrahydroquinoline 
• 123629-22-1 (RS)-2-cyclohexyl-1,2,3,4-tetrahydroquinoline 
• 5855-52-7 2-phenylquinolin-4-amine 
• 64388-07-4 2‐(3‐nitrophenyl)quinoline 
• 64388-23-4 2-(4-nitrophenyl)quinoline 
• 243-68-5 benzo[4,5]thieno[3,2-b]quinoline 
• 136949-24-1 2-perfluorohexyl-2-phenyl-1,2-dihydroquinoline 
• 119408-45-6 2-(quinolin-2-yl)phenyltellurium(IV) tribromide 

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.).

Bioinspired Radical-Mediated Transition-Metal-Free Synthesis of N-Heterocycles under Visible Light

A redox-active iminoquinone motif connected with π-delocalized pyrene core has been reported that can perform efficient two-electron oxidation of a class of substrates. The design of the molecule was inspired by the organic redox cofactor topaquinone (TPQ), which executes amine oxidation in the enzyme, copper amine oxidase. Easy oxidation of both primary and secondary alcohols happened in the presence of catalytic KOtBu, which could reduce the ligand backbone to its iminosemiquinonate form under photoinduced conditions. Moreover, this easy oxidation of alcohols under aerobic condition could be elegantly extended to multi-component, one-pot coupling for the synthesis of quinoline and pyrimidine. This organocatalytic approach is very mild (70 °C, 8 h) compared to a multitude of transition-metal catalysts that have been used to prepare these heterocycles. A detailed mechanistic study proves the intermediacy of the iminosemiquinonate-type radical and a critical hydrogen atom transfer step to be involved in the dehydrogenation reaction.