612-58-8

Basic information

• Product Name: 3-Methylquinoline
• Synonyms: NSC 109149;Quinoline, 3-methyl-;3-methyl-quinolin;3-METHYLQUINOLINE;3-Methylquinoline, 98+%;7-Chloro-8-methylquinolin-4-ol;Ethyl 5-chloro-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate;3-methyquinoline
• CAS NO: 612-58-8
• Molecular Formula: C₁₀H₉N
• Molecular Weight: 265.69
• EINECS: 210-315-7
• Product Categories: Building Blocks;C8 to C10;Cell Biology;Chemical Synthesis;Heterocyclic Building Blocks;M;blocks;Quinolines;Carboxes;FluoroCompounds;Quinoline Derivertives;Hydroxyquinolines;Alkylquinolines;Quinolinecarboxylic Acids, etc.;Quinoline;Building Blocks;Heterocyclic Building Blocks;Aromatics;Heterocycles;Bioactive Small Molecules
• Mol File: 612-58-8.mol
• Article Data: 65

Chemical Properties

• Melting Point: 16-17 °C(lit.)
• Boiling Point: 252-253 °C(lit.)
• Flash Point: >230 °F
• Appearance: colorless to light yellow liquid
• Density: 1.069 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0206mmHg at 25°C
• Refractive Index: n20/D 1.615(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 5.17±0.11(Predicted)
• BRN: 110325
• CAS DataBase Reference: 3-Methylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methylquinoline(612-58-8)
• EPA Substance Registry System: 3-Methylquinoline(612-58-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-40-68-22
• Safety Statements: 26-27-36/37/39-45
• WGK Germany: 3
• RTECS: VC0527000
• Hazardous Substances Data: 612-58-8(Hazardous Substances Data)

Usage

Description

3-Methylquinoline is a quinoline derivative, characterized as a colorless to light yellow liquid. It is widely utilized in the synthesis of various compounds, including dyes, food coloring agents, pharmaceutical reagents, and pH indicators. Its versatile applications span across different industries, making it a valuable component in numerous industrial processes.

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

• 75-21-8 oxirane 
• 62-53-3 aniline 
• 64-19-7 acetic acid 
• 5827-78-1 N-methyl-N-phenylpropanamide 
• 50-00-0 formaldehyd 
• 123-38-6 propionaldehyde 
• 109-87-5 Dimethoxymethane 
• 7796-86-3 1,3-diethoxy-2-methyl-propan-2-ol 
• 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 
• 73177-27-2 2-ethyl-1,4-dihydro-2H-benz[d][1,3]oxazine 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 3222-49-9 5-methylnicotinic acid 
• 13669-42-6 3-quinolylcarboxaldehyde 
• 1873-55-8 3-methylquinoline N-oxide 
• 28712-62-1 3-methyl-5,6,7,8-tetrahydroquinoline 
• 20668-20-6 3-methyl-1,2,3,4-tetrahydroquinoline 
• 6480-68-8 quinoline-3-carboxylic acid 
• 103754-53-6 3-methyl-5-nitroquinoline 
• 2801-32-3 3-methyl-8-nitroquinoline 
• 74212-52-5 1-phenyl-2-(quinolin-3-yl)ethan-1-one 
• 57443-82-0 1,1-diphenyl-2-(3-quinolyl)ethanol 
• 139962-74-6 2-Phenyl<1H>pyrrolo<2,3-b>quinoline 
• 139962-75-7 2-(4-Methoxyphenyl)<1H>pyrrolo<2,3-b>quinoline 
• 53636-65-0 5-methyl-pyridine-2,3-dicarboxylic acid 
• 153886-69-2 3-methyl-8-quinolinesulfonic acid 

Relevant articles and documents

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.

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.

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.