61687-26-1

Basic information

• Product Name: 7-Chloro-2-phenyl-quinoline
• Synonyms: 7-Chloro-2-phenyl-quinoline;2-Phenyl-7-chloroquinoline
• CAS NO: 61687-26-1
• Molecular Formula: C₁₅H₁₀ClN
• Molecular Weight: 239.6996
• EINECS: 1312995-182-4
• Mol File: 61687-26-1.mol

Chemical Properties

• Melting Point: 105-106℃ (ethyl ether )
• Boiling Point: 394.0±27.0 °C(Predicted)
• Appearance: /
• Density: 1.235±0.06 g/cm3 (20℃ 760 Torr)
• Storage Temp.: 2-8°C
• PKA: 3.01±0.14(Predicted)
• CAS DataBase Reference: 7-Chloro-2-phenyl-quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Chloro-2-phenyl-quinoline(61687-26-1)
• EPA Substance Registry System: 7-Chloro-2-phenyl-quinoline(61687-26-1)

Safety Data

• Hazardous Substances Data: 61687-26-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
7-Chloro-2-phenyl-Quinoline is used as a chemical intermediate for the synthesis of various complex organic molecules. Its unique structure allows it to serve as a building block in the preparation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
In the field of organic chemistry, 7-chloro-2-phenyl-Quinoline is used as a research compound to study the reactivity and properties of quinolines and their derivatives. It aids in understanding the behavior of these compounds in different reaction conditions and their potential applications in various industries.
Used in Pharmaceutical Industry:
7-Chloro-2-phenyl-Quinoline is used as a key component in the development of new drugs. Its structure can be modified to create novel compounds with potential therapeutic applications, such as antimalarial, antibacterial, or anticancer agents. 7-chloro-2-phenyl-Quinoline's versatility in chemical reactions makes it a valuable asset in the search for new pharmaceutical leads.
Used in Agrochemical Industry:
In the agrochemical sector, 7-chloro-2-phenyl-Quinoline is used as a starting material for the synthesis of new pesticides or herbicides. Its chemical properties can be tailored to create compounds that are effective in controlling pests and weeds, thus contributing to improved crop protection and yield.
Used in Material Science:
7-Chloro-2-phenyl-Quinoline is used as a component in the development of new materials with specific properties, such as conductivity, magnetism, or luminescence. Its incorporation into these materials can lead to the creation of advanced materials for use in electronics, sensors, or other high-tech applications.

Upstream product

• 98-86-2 acetophenone 
• 104-55-2 3-phenyl-propenal 
• 108-42-9 3-chloro-aniline 
• 612-61-3 7-chloroquinoline 
• 100-59-4 phenylmagnesium chloride 
• 100-52-7 benzaldehyde 
• 79-10-7 acrylic acid 
• 123-91-1 1,4-dioxane 
• 37585-16-3 (2-amino-4-chlorophenyl)methanol 
• 5551-11-1 4-Chloro-2-nitrobenzaldehyde 
• 1636-34-6 2,3-diphenyl-2,3-butanediol 
• 79-24-3 Nitroethane 
• 98-80-6 phenylboronic acid 
• 100-63-0 phenylhydrazine 

Downstream Products

• 1613216-41-3 5,9-diphenyl-7-(2-phenylquinolin-7-yl)-7H-benzo[c]carbazole 
• 1159987-42-4 (S)-7-chloro-2-phenyl-1,2,3,4-tetrahydroquinoline 
• 867164-54-3 2-phenyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline 

Relevant articles and documents

Visible-Light-Induced Amination of Quinoline at the C8 Position via a Postcoordinated Interligand-Coupling Strategy under Mild Conditions

The postcoordinated interligand-coupling strategy provides a useful and complementary protocol for synthesizing polydentate ligands. Herein, diastereoselective photoreactions of Λ-[Ir(pq)2(d-AA)] (Λ-d) and Λ-[Ir(pq)2(l-AA)] (Λ-l, where pq is 2-phenylquino

Ruthenium-catalyzed acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones to quinolines in the presence of carbonate salt

A ruthenium complex bearing a functional 2,2′-bibenzimidazole ligand [(p-cymene)Ru(BiBzImH2)Cl][Cl] was designed, synthesized and found to be a general and highly efficient catalyst for the synthesis of quinolines via acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones in the presence of carbonate salt. It was confirmed that NH units in the ligand are crucial for catalytic activity. The application of this catalytic system for the scale-gram synthesis of biologically active molecular was also undertaken. Notably, this research exhibits new potential of metal–ligand bifuctional catalysts for acceptorless dehydrogenative reactions.

Zinc Stabilized Azo-anion Radical in Dehydrogenative Synthesis of N-Heterocycles. An Exclusively Ligand Centered Redox Controlled Approach

Herein we report an exclusively ligand-centered redox controlled approach for the dehydrogenation of a variety of N-heterocycles using a Zn(II)-stabilized azo-anion radical complex as the catalyst. A simple, easy-to-prepare, and bench-stable Zn(II)-complex (1b) featuring the tridentate arylazo pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline, in the presence of zinc-dust, undergoes reduction to form the azo-anion radical species [1b]- which efficiently dehydrogenates various saturated N-heterocycles such as 1,2,3,4-tetrahydro-2-methylquinoline, 1,2,3,4-tetrahydro-isoquinoline, indoline, 2-phenyl-2,3-dihydro-1H-benzoimidazole, 2,3-dihydro-2-phenylquinazolin-4(1H)-one, and 1,2,3,4-tetrahydro-2-phenylquinazolines, among others, under air. The catalyst has further been found to be compatible with the cascade synthesis of these N-heterocycles via dehydrogenative coupling of alcohols with other suitable coupling partners under air. Mechanistic investigation reveals that the dehydrogenation reactions proceed via a one-electron hydrogen atom transfer (HAT) pathway where the zinc-stabilized azo-anion radical ligand abstracts the hydrogen atom from the organic substrate(s), and the whole catalytic cycle proceeds via the exclusive involvement of the ligand-centered redox events where the zinc acts only as the template.

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.

Mild and efficient copper-catalyzed oxidative cyclization of oximes with 2-aminobenzyl alcohols at room temperature: synthesis of polysubstituted quinolines

A simple and efficient ligand-free Cu-catalyzed protocol for the synthesis of polysubstituted quinolinesviaoxidative cyclization of oxime acetates with 2-aminobenzyl alcohols at room temperature has been developed. The presented approach provides a new synthetic pathway leading to polysubstituted quinolines with good functional group tolerance under mild conditions. Moreover, this transformation can be applied for the preparation of quinolines on a gram scale. Oxime acetates serve as the internal oxidants in the reactions, thus making this method very attractive.

Enantioselective Synthesis of Tetrahydroquinolines via One-Pot Cascade Biomimetic Reduction?

A novel and efficient protocol for the synthesis of chiral tetrahydroquinoline derivatives with excellent enantioselectivities and high yields has been developed through one-pot cascade biomimetic reduction. The detailed reaction pathway includes the acid-catalyzed and ruthenium-catalyzed formation of aromatic quinoline intermediates and biomimetic asymmetric reduction.

Preparation method and application of 2-aryl quinoline derivatives

The invention discloses a preparation method and application of 2-aryl quinoline derivatives, and belongs to the technical field of novel organic synthesis methods. According to the preparation method, in a Schlenk tube with a screw cap, aromatic aldehyde and aromatic amine react with a cyclic ether compound under the action of a catalytic system composed of a copper salt, trifluoromethane sulfonic acid and air, and 2-aryl quinoline compounds are obtained. A cyclic ether compound is used as a dicarbon synthon for the first time, and a series of 2-aryl quinoline compounds are prepared. The preparation method has the advantages of mild reaction conditions, wide reaction substrate universality, short reaction time, high target product yield, and simple reaction operation and post-treatment process. The compounds have a wide application prospect in the field of medicinal chemistry.

Organometal-Free Arylation and Arylation/Trifluoroacetylation of Quinolines by Their Reaction with CF3-ynones and Base-Induced Rearrangement

The reaction of quinolines with CF3-ynones resulted in the formation of 1,3-oxazinoquinolines. Subsequent treatment of the reaction mixture with a base initiated deep structural transformation of primary products. Both steps proceed in very high yield. As a result, unusual rearrangement of 1,3-oxazinoquinolines to form either 2-arylquinolines or 2-aryl-3-trifluoroacetylquinolines was discovered. The decisive role of the base in the reaction direction was shown. Using these reactions, highly efficient pathways to 2-arylquinolines and 2-aryl-3-trifluoroacetylquinolines were elaborated to provide the corresponding compounds in high yields using a simple one-pot procedure. The possible mechanism of rearrangement is discussed.

Preparation of 2-Arylquinolines from 2-Arylethyl Bromides and Aromatic Nitriles with Magnesium and N -Iodosuccinimide

Treatment of 2-arylethylmagnesium bromides, prepared from 2-arylethyl bromides and magnesium, with aromatic nitriles, followed by reaction with water and then with N -iodosuccinimide under irradiation with a tungsten lamp, gave the corresponding 2-arylquinolines in good to moderate yields under transition-metal-free conditions. 2-Alkylquinolines could be also obtained in moderate yields by the same procedure with 2-arylethyl bromides, magnesium, aliphatic nitriles bearing a secondary alkyl group, and N -iodosuccinimide.

The synthesis of quinolines: via denitrogenative palladium-catalyzed cascade reaction of o -aminocinnamonitriles with arylhydrazines

The first example of the palladium-catalyzed cascade reaction of o-aminocinnamonitriles with arylhydrazines has been achieved, providing an efficient synthetic pathway to access quinolines with moderate to good yields. Preliminary mechanistic experiments