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Usage

Uses

Used in Chemical Synthesis:
3-Methylquinoline is used as a key intermediate in the synthesis of dyes, food coloring agents, and pharmaceutical reagents. Its chemical properties make it a suitable candidate for these applications, allowing for the creation of a wide range of products with diverse colors and functionalities.
Used in Environmental Applications:
It can be degraded efficiently by QL-degrading bacteria, which highlights its potential use in environmental applications for biodegradation and waste management.
Used in Research and Development:
3-Methylquinoline may be used as a carbon, nitrogen, and energy supplement to investigate its degradation by Comamonas testosteroni 63, providing valuable insights into the bacterial degradation process and its potential applications in bioremediation.
Used in Coordination Chemistry:
3-Methylquinoline is used as a ligand in the preparation of tetra-μ-benzoato-bis[(3-methylquinoline)copper(II)], a paddle-wheel-type dinuclear complex. This application showcases its utility in coordination chemistry and the development of novel metal complexes with potential applications in various fields.

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 569, 1991 DOI: 10.1016/S0040-4039(00)74829-5

InChI:InChI=1/C10H9N/c1-8-6-9-4-2-3-5-10(9)11-7-8/h2-7H,1H3

Upstream product

• 64-19-7 acetic acid 
• 50-00-0 formaldehyd 
• 123-38-6 propionaldehyde 
• 109-87-5 Dimethoxymethane 
• 529-23-7 o-aminobenzaldehyde 
• 62-53-3 aniline 
• 98-47-5 3-Nitrobenzenesulfonic acid 
• 79476-07-6 3-Iodoquinoline 
• 59201-86-4 tris(diethylamino)sulfonium difluorotrimethylsiliconate 
• 57876-69-4 2-chloro-3-methyl-quinoline 
• 201230-82-2 carbon monoxide 
• 32704-22-6 2-allyl-phenylamine 
• 131470-23-0 1-(2'-aminophenyl)prop-2-en-1-ol 
• 22892-88-2 1,4-dimethyl-5-phenyl-2-aza-1-oxapentadiene 

Downstream Products

• 3222-49-9 5-methylnicotinic acid 
• 53636-65-0 5-methyl-pyridine-2,3-dicarboxylic acid 
• 120277-70-5 3-(bromomethyl)quinoline 
• 153886-69-2 3-methyl-8-quinolinesulfonic acid 
• 713077-21-5 3-methyl-1-phenacyl-quinolinium bromide 
• 74863-82-4 8-(chlorosulphonyl)-3-methylquinoline 
• 1208524-11-1 C₁₇H₁₂FN₃O 
• 1208524-08-6 C₁₇H₁₃N₃O 
• 1208524-10-0 C₁₈H₁₅N₃O 
• 1208524-13-3 C₁₇H₁₂ClN₃O 
• 1275591-25-7 3-methyl-8-phenylquinoline 
• 19051-05-9 3-methylquinoline-2-carbonitrile 
• 57876-69-4 2-chloro-3-methyl-quinoline 
• 35740-86-4 2-bromo-3-methylquinoline 

Relevant academic research and scientific papers

Potent mutagenic potential of 4-methylquinoline: Metabolic and mechanistic considerations

4-Methylquinoline (4-MeQ) showed an extraordinarily potent mutagenicity when compared to quinolone and isomeric methylquinolines. The major metabolite of 4-MeQ was 4- hydroxymethylquinoline, which was not mutagenic under the assay condition employed. Deuteration of the methyl group of 4-MeQ resulted in a decrease in the amount of the hydroxymethyl metabolic and an increase in mutagenicity, indicating that hydroxylation of the substituent methyl group is a detoxication process. A 3-chloro derivative of 4-MeQ was proven to be non-mutagenic. 4-Ethyl- quinoline, as well as 4-hydroxymethylquinoline, was much less mutagenic than 4-MeQ. Taking account of the structure-mutagenicity relationship, a possible mechanism is proposed for the potent mutagenic potential of 4-MeQ.

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 Using Hantzsch Esters as Mild Reducing Agents

Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).

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.

Highly Ordered Mesoporous Cobalt Oxide as Heterogeneous Catalyst for Aerobic Oxidative Aromatization of N-Heterocycles

N-heterocycles are key structures for many pharmaceutical intermediates. The synthesis of such units normally is conducted under homogeneous catalytic conditions. Among all methods, aerobic oxidative aromatization is one of the most effective. However, in homogeneous conditions, catalysts are difficult to be recycled. Herein, we report a heterogeneous catalytic strategy with a mesoporous cobalt oxide as catalyst. The developed protocol shows a broad applicability for the synthesis of N-heterocycles (32 examples, up to 99 % yield), and the catalyst presents high turnover numbers (7.41) in the absence of any additives. Such a heterogenous approach can be easily scaled up. Furthermore, the catalyst can be recycled by simply filtration and be reused for at least six times without obvious deactivation. Comparative studies reveal that the high surface area of mesoporous cobalt oxide plays an important role on the catalytic reactivity. The outstanding recycling capacity makes the catalyst industrially practical and sustainable for the synthesis of diverse N-heterocycles.

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.

Generation of Alkyl Radical through Direct Excitation of Boracene-Based Alkylborate

The generation of tertiary, secondary, and primary alkyl radicals has been achieved by the direct visible-light excitation of a boracene-based alkylborate. This system is based on the photophysical properties of the organoboron molecule. The protocol is applicable to decyanoalkylation, Giese addition, and nickel-catalyzed carbon-carbon bond formations such as alkyl-aryl cross-coupling or vicinal alkylarylation of alkenes, enabling the introduction of various C(sp3) fragments to organic molecules.

Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source

Methylation of organohalides represents a valuable transformation, but typically requires harsh reaction conditions or reagents. We report a radical approach for the methylation of (hetero)aryl chlorides using nickel/photoredox catalysis wherein trimethyl orthoformate, a common laboratory solvent, serves as a methyl source. This method permits methylation of (hetero)aryl chlorides and acyl chlorides at an early and late stage with broad functional group compatibility. Mechanistic investigations indicate that trimethyl orthoformate serves as a source of methyl radical via β-scission from a tertiary radical generated upon chlorine-mediated hydrogen atom transfer.

Rh-Catalyzed C-H Amination/Annulation of Acrylic Acids and Anthranils by Using -COOH as a Deciduous Directing Group: An Access to Diverse Quinolines

A method for the synthesis of diverse polysubstituted quinolines from readily available acrylic acids and anthranils has been developed. The weakly coordinating -COOH directing group, which can be tracelessly removed in the cascade cyclization, is essential for this reaction. Diverse polysubstituted quinolines were obtained under mild reaction conditions with simple H2O and CO2 as byproducts. More importantly, 1,2,3,4-tetrahydroacridine, which is the core skeleton of tacrine (an Alzheimer's disease drug), was conveniently synthesized.

Gold-Catalyzed Iminations of Terminal Propargyl Alcohols with Anthranils with Atypical Chemoselectivity for C(1)-Additions and 1,2-Carbon Migration

This work reports gold-catalyzed iminations of terminal propargyl alcohols with anthranils or isoxazoles to yield E-configured α-amino-2-en-1-ones and -1-als with complete chemoselectivity. These catalytic iminations occur exclusively with C(1)-nucleophilic additions on terminal alkynes, in contrast to a typical C(2)-route. For 3,3-dialkylprop-1-yn-3-ols, a methyl substituent is superior to long alkyl chains as the 1,2-migration groups toward α-imino gold carbenes. For secondary prop-1-yn-3-ols, phenyl, vinyl, and cyclopropyl substituents are better than hydrogen as the migrating groups, obviating typical gold carbene reactions. DFT calculations have been performed to rationalize the observed C(1)-regioselectivity and the preferable cyclopropyl migration based on gold carbene pathways.