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Usage

Uses

Used in Research and Development:
6-Chloroquinoline is used as a research chemical for various scientific investigations and experiments. It serves as a valuable compound in the field of organic chemistry, contributing to the understanding of chemical reactions and molecular structures.
Used in Synthesis:
6-Chloroquinoline is utilized in the synthesis of 3-methyl-3H-imidazo[4,5-f]quinolin-2-amine, a compound that may have potential applications in various industries.
Used as a Catalyst:
In the chemical industry, 6-Chloroquinoline is used as a catalyst for the high yield preparation of ethoxycarbonyl isothiocyanate, a process that benefits from its unique chemical properties and reactivity.

InChI:InChI=1/C9H6ClN/c10-8-3-4-9-7(6-8)2-1-5-11-9/h1-6H

Upstream product

• 106-47-8 4-chloro-aniline 
• 56-81-5 glycerol 
• 49716-18-9 6-chloro-1,2,3,4-tetrahydroquinoline 
• 18437-66-6 N-(t-butoxycarbonyl)-4-chloroaniline 
• 1611-78-5 1,3-bis-dimethylaminotrimethinium perchlorate 
• 156-87-6 propan-1-ol-3-amine 
• 7647-01-0 hydrogenchloride 
• 333383-88-3 6-chloro-1-methanesulfonyl-1,2-dihydro-quinoline 
• 100-00-5 4-chlorobenzonitrile 
• 4284-51-9 N-(mesyl)-4-chloroaniline 
• 5332-25-2 6-bromoquinoline 
• 108-42-9 3-chloro-aniline 
• 504-63-2 trimethyleneglycol 
• 104-55-2 3-phenyl-propenal 

Downstream Products

• 6634-83-9 6-chloro-1-(2-[2]naphthyl-2-oxo-ethyl)-quinolinium; bromide 
• 6277-48-1 6-chloro-1-(4-methoxy-phenacyl)-quinolinium; bromide 
• 6267-54-5 6-chloro-1-(4-iodo-phenacyl)-quinolinium; bromide 
• 32596-83-1 6-chloro-1-methylquinolin-1-ium iodide 
• 68527-66-2 6-chloro-8-nitroquinoline 
• 86984-32-9 6‐chloro‐5‐nitroquinoline 
• 406463-06-7 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline 
• 612-95-3 6-phenylquinoline 
• 580-16-5 6-hydroxyquinoline 
• 1810-67-9 6-chloro-2-hydroxy-quinoline 
• 1810-72-6 2,6-dichloroquinoline 
• 4203-18-3 4,6-dichloroquinoline 
• 5470-75-7 8-amino-6-chloroquinoline 
• 703-66-2 6,8-Dichloroquinoline 

Relevant academic research and scientific papers

Method for realizing oxidative dehydrogenation of nitrogen-containing heterocyclic ring by using biomass-based carbon material

The invention provides a method for realizing oxidative dehydrogenation of a nitrogen-containing heterocyclic ring by using a biomass-based carbon material, and belongs to the field of organic synthesis. According to the method, the raw materials of the biomass-based carbon material comprise wheat, sorghum, rice, corn straw, wheat straw, peanut shells, sesame shells, bean shells and the like, and are crushed and then ground into powder, the powder is fully mixed with an inorganic alkali, and calcination is performed in an inert gas atmosphere to prepare the biomass-based carbon material; and by using air as an oxygen source, at a temperature of 50-120 DEG C, oxidative dehydrogenation of nitrogen-containing heterocyclic compounds to synthesize quinoline compounds, isoquinoline compounds, acridine compounds, quinazoline compounds, indole compounds, imine compounds, and even quinoline compounds with pharmaceutical activity can be achieved. According to the present invention, easily available wheat flour is adopted as a raw material to prepare a non-metal catalyst, the alkali is not added during the reaction process, and a remarkable industrial application prospect is achieved.

Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions

Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is

Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies

We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.

Metal–Organic Layers Hierarchically Integrate Three Synergistic Active Sites for Tandem Catalysis

We report the design of a bifunctional metal–organic layer (MOL), Hf12-Ru-Co, composed of [Ru(DBB)(bpy)2]2+ [DBB-Ru, DBB=4,4′-di(4-benzoato)-2,2′-bipyridine; bpy=2,2′-bipyridine] connecting ligand as a photosensitizer and Co(dmgH)2(PPA)Cl (PPA-Co, dmgH=dimethylglyoxime; PPA=4-pyridinepropionic acid) on the Hf12 secondary building unit (SBU) as a hydrogen-transfer catalyst. Hf12-Ru-Co efficiently catalyzed acceptorless dehydrogenation of indolines and tetrahydroquinolines to afford indoles and quinolones. We extended this strategy to prepare Hf12-Ru-Co-OTf MOL with a [Ru(DBB)(bpy)2]2+ photosensitizer and Hf12 SBU capped with triflate as strong Lewis acids and PPA-Co as a hydrogen transfer catalyst. With three synergistic active sites, Hf12-Ru-Co-OTf competently catalyzed dehydrogenative tandem transformations of indolines with alkenes or aldehydes to afford 3-alkylindoles and bisindolylmethanes with turnover numbers of up to 500 and 460, respectively, illustrating the potential use of MOLs in constructing novel multifunctional heterogeneous catalysts.

Iron(II)-Catalyzed Aerobic Biomimetic Oxidation of N-Heterocycles

Herein, an iron(II)-catalyzed biomimetic oxidation of N-heterocycles under aerobic conditions is described. The dehydrogenation process, involving several electron-transfer steps, is inspired by oxidations occurring in the respiratory chain. An environmentally friendly and inexpensive iron catalyst together with a hydroquinone/cobalt Schiff base hybrid catalyst as electron-transfer mediator were used for the substrate-selective dehydrogenation reaction of various N-heterocycles. The method shows a broad substrate scope and delivers important heterocycles in good-to-excellent yields.

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

Geometric and electronic effects on the performance of a bifunctional Ru2P catalyst in the hydrogenation and acceptorless dehydrogenation of N-heteroarenes

The development of bifunctional catalysts for the efficient hydrogenation and acceptorless dehydrogenation of N-heterocycles is a challenge. In this study, Ru2P/AC effectively promoted reversible transformations between unsaturated and saturated N-heterocycles affording yields of 98% and 99%, respectively. Moreover, a remarkable enhancement in the reusability of Ru2P/AC was observed compared with other Ru-based catalysts. According to density functional theory calculations, the superior performance of Ru2P/AC was ascribed to specific synergistic factors, namely geometric and electronic effects induced by P. P greatly reduced the large Ru-Ru ensembles and finely modified the electronic structures, leading to a low reaction barrier and high desorption ability of the catalyst, further boosting the hydrogenation and acceptorless dehydrogenation processes.

Superacid-promoted synthesis of quinoline derivatives

A series of vinylogous imines have been prepared from anilines and cinnamaldehydes. These substrates react in superacidic media to provide quinolines and related compounds. A mechanism for the conversion is proposed which involves the cyclization of dicationic superelectrophilic intermediates. Aromatization of the quinoline ring is thought to occur by superacid-promoted elimination of benzene.

Rh/TiO2-Photocatalyzed Acceptorless Dehydrogenation of N-Heterocycles upon Visible-Light Illumination

TiO2 is an effective and extensively employed photocatalyst, but its practical use in visible-light-mediated organic synthesis is mainly hindered by its wide band gap energy. Herein, we have discovered that Rh-photodeposited TiO2 nanoparticles selectively dehydrogenate N-heterocyclic amines with the concomitant generation of molecular hydrogen gas in an inert atmosphere under visible light (λmax = 453 nm) illumination at room temperature. Initially, a visible-light-sensitive surface complex is formed between the N-heterocycle and TiO2. The acceptorless dehydrogenation of N-heterocycles is initiated by direct electron transfer from the HOMO energy level of the amine via the conduction band of TiO2 to the Rh nanoparticle. The reaction condition was optimized by examining different photodeposited noble metals on the surface of TiO2 and solvents, finding that Rh0 is the most efficient cocatalyst, and 2-propanol is the optimal solvent. Structurally diverse N-heterocycles such as tetrahydroquinolines, tetrahydroisoquinolines, indolines, and others bearing electron-deficient as well as electron-rich substituents underwent the dehydrogenation in good to excellent yields. The amount of released hydrogen gas evinces that only the N-heterocyclic amines are oxidized rather than the dispersant. This developed method demonstrates how UV-active TiO2 can be employed in visible-light-induced synthetic dehydrogenation of amines and simultaneous hydrogen storage applications.

Visible-Light-Promoted Efficient Aerobic Dehydrogenation of N-Heterocycles by a Tiny Organic Semiconductor Under Ambient Conditions

An efficient reusable catalytic system has been developed based on perylene diimide (PDI) organic semiconductor for the aerobic dehydrogenation of N-heterocycles with visible light. This practical catalytic system without any additives proceeds under ambient conditions. The minute aggregates of PDI molecules on the surface of SiO2 nanospheres form tiny organic semiconductors, resulting in high-efficiency photo-oxidative activity. Notably, the robustness of this method is demonstrated by the synthesis of a wide range of N-heteroarenes, gram-scale experiments as well as reusability tests.