64388-23-4

Basic information

• Product Name: Quinoline, 2-(4-nitrophenyl)-
• CAS NO: 64388-23-4
• Molecular Formula: C15H10N2O2
• Molecular Weight: 250.257
• Mol File: 64388-23-4.mol

Chemical Properties

• CAS DataBase Reference: Quinoline, 2-(4-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoline, 2-(4-nitrophenyl)-(64388-23-4)
• EPA Substance Registry System: Quinoline, 2-(4-nitrophenyl)-(64388-23-4)

Safety Data

• Hazardous Substances Data: 64388-23-4(Hazardous Substances Data)

Upstream product

• 612-96-4 2-Phenylquinoline 
• 49678-08-2 3-(4-nitrophenyl)-propenal 
• 62-53-3 aniline 
• 7697-37-2 nitric acid 
• 5344-90-1 2-Aminobenzyl alcohol 
• 100-19-6 (4-nitrophenyl)ethanone 
• 95-53-4 o-toluidine 
• 1734-79-8 3-(4-nitrophenyl)-2-propenal 
• 1124190-97-1 C₁₆H₁₁ClN₂O₃ 
• 612-62-4 2-Chloroquinoline 
• 171364-83-3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene 
• 555-16-8 4-nitrobenzaldehdye 
• 79-10-7 acrylic acid 
• 937-31-5 (4-Nitrophenyl)acetylene 

Downstream Products

• 64388-18-7 2-(4-nitrophenyl)quinoline 1-oxide 

Relevant articles and documents

Mild and Robust Stille Reactions in Water using Parts Per Million Levels of a Triphenylphosphine-Based Palladacycle

An inexpensive and new triphenylphosphine-based palladacycle has been developed as a pre-catalyst, leading to highly effective Stille cross-coupling reactions in water under mild reaction conditions. Only 500–1000 ppm of Pd suffices for couplings involving a variety of aryl/heteroaryl halides with aryl/hetaryl stannanes. Several drug intermediates can be prepared using this catalyst in aqueous nanoreactors formed by 2 wt % Brij-30 in water.

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.

Porous FeO(OH) Dispersed on Mg-Al Hydrotalcite Surface for One-Pot Synthesis of Quinoline Derivatives

The use of ubiquities elements such as iron instead of expensive precious metals as catalysts is one goal toward realizing environmentally benign synthetic chemistry. Here, we report that porous FeO(OH) dispersed on Mg?Al hydrotalcite acts as a bifunctional heterogeneous catalyst in the one-pot synthesis of 2-substituted quinoline derivatives through dehydrogenative oxidation-cyclization reactions. The catalyst was prepared by a simple grafting method using FeCl3 and Mg?Al hydrotalcite. The prepared porous FeO(OH) possesses a higher surface area than those previously reported for α-FeO(OH) particles. The one-pot quinoline synthesis proceeded effectively under non-noble-metal catalysis in air without requiring additional homogeneous bases or solvents.

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.

Half-Sandwich Ruthenium Complexes for One-Pot Synthesis of Quinolines and Tetrahydroquinolines: Diverse Catalytic Activity in the Coupled Cyclization and Hydrogenation Process

Four types of half-sandwich ruthenium complexes with an N,O-coordinate mode based on hydroxyindanone-imine ligands have been prepared in good yields. These stable ruthenium complexes exhibited high activity in the catalytic synthesis of quinolines from the reactions of amino alcohols with different types of ketones or secondary alcohols under very mild conditions. Moreover, the methodology for the direct one-pot synthesis of tetrahydroquinoline derivatives from amino alcohols and ketones has been also developed on the basis of the continuous catalytic activity of this ruthenium catalyst in the selective hydrogenation of the obtained quinoline derivatives with a low catalyst loading. The corresponding products, quinolines and tetrahydroquinoline derivatives, were afforded in good to excellent yields. The efficient and diverse catalytic activity of these ruthenium complexes suggested their potential large-scale application. All of the ruthenium complexes were characterized by various spectroscopies to confirm their structures.

Metal-Ligand Cooperative Approach to Achieve Dehydrogenative Functionalization of Alcohols to Quinolines and Quinazolin-4(3 H)-ones under Mild Aerobic Conditions

A simple metal-ligand cooperative approach for the dehydrogenative functionalization of alcohols to various substituted quinolines and quinazolin-4(3H)-ones under relatively mild reaction conditions (≤90 °C) is reported. Simple and easy-to-prepare air-stable Cu(II) complexes featuring redox-active azo-aromatic scaffolds, 2-arylazo-(1,10-phenanthroline) (L1,2), are used as catalyst. A wide variety of substituted quinolines and quinazolin-4(3H)-ones were synthesized in moderate to good isolated yields via dehydrogenative coupling reactions of various inexpensive and easily available starting materials under aerobic conditions. A few control experiments and deuterium labeling studies were carried out to understand the mechanism of the dehydrogenative coupling reactions, which indicate that both copper and the coordinated azo-aromatic ligand participate in a cooperative manner during the catalytic cycle.

Dehydrogenative Synthesis of Quinolines, 2-Aminoquinolines, and Quinazolines Using Singlet Diradical Ni(II)-Catalysts

Simple, straightforward, and atom economic methods for the synthesis of quinolines, 2-aminoquinolines, and quinazolines via biomimetic dehydrogenative condensation/coupling reactions, catalyzed by well-defined inexpensive and easy to prepare singlet diradical Ni(II)-catalysts featuring two antiferromagnetically coupled singlet diradical diamine type ligands are described. Various polysubstituted quinolines, 2-aminoquinolines, and quinazolines were synthesized in moderate to good yields from different low-cost and readily accessible starting materials. Several control experiments were carried out to get insight into the reaction mechanism which shows that the nickel and the coordinated diamine ligands participate in a synergistic way during the dehydrogenation of alcohols.

π-Allylpalladium Species in Micelles of FI-750-M for Sustainable and General Suzuki-Miyaura Couplings of Unactivated Quinoline Systems in Water

General, clean, and sustainable Suzuki-Miyaura cross-couplings of 2-and 4-quinoline and isoquinoline systems have been demonstrated with use of π-allyl Pd catalyst in the nanomicelles of environmentally benign, proline-derived surfactant FI-750-M. Optimiz

A nickel catalyzed acceptorless dehydrogenative approach to quinolines

A general, efficient and environmentally benign, one-step synthesis of substituted quinoline derivatives was achieved by acceptorless dehydrogenative coupling of o-aminobenzylalcohols with ketones and secondary alcohols catalyzed by a cheap, earth abundant and easy to prepare nickel catalyst [Ni(MeTAA)], featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)). A wide variety of substituted quinolines were synthesized in high yields starting from readily available o-aminobenzylalcohols and ketones or secondary alcohols. A few controlled reactions were carried out to establish the acceptorless dehydrogenative nature of the reactions.

Palladium-catalyzed synthesis of quinolines from allyl alcohols and anilines

A process for quinoline synthesis through palladium-catalyzed oxidative cyclization of aryl allyl alcohols and anilines is described. This process works in the absence of acid, base and any other additive and has a broad substrate scope, tolerating electron-withdrawing groups such as nitryl, trifluoromethyl and so on. A series of quinolines are prepared in satisfactory yields.