7661-55-4

Basic information

• Product Name: 5-Methylquinoline
• Synonyms: 5-METHYLQUINOLINE
• CAS NO: 7661-55-4
• Molecular Formula: C₁₀H₉N
• Molecular Weight: 143.19
• EINECS: 231-630-6
• Product Categories: Quinoline Derivertives
• Mol File: 7661-55-4.mol

Chemical Properties

• Melting Point: 19°C
• Boiling Point: 257.85°C
• Flash Point: 104.4°C
• Appearance: /
• Density: 1.0832
• Vapor Pressure: 0.0175mmHg at 25°C
• Refractive Index: 1.6219
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.2(at 20℃)
• CAS DataBase Reference: 5-Methylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methylquinoline(7661-55-4)
• EPA Substance Registry System: 5-Methylquinoline(7661-55-4)

Safety Data

• RIDADR: 2810
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 7661-55-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Methylquinoline is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of antimalarial drugs. Its unique chemical structure allows it to be a valuable component in creating effective treatments against malaria.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Methylquinoline is utilized as a precursor in the production of pesticides and other agrochemicals, leveraging its chemical properties to enhance the effectiveness of these products in agricultural applications.
Used in Dye and Pigment Industry:
5-Methylquinoline is employed as a building block in the synthesis of dyes and pigments, where its aromatic nature contributes to the color intensity and stability of the final products.
Used in Research and Development:
5-Methylquinoline is used as a subject of research for its potential therapeutic applications in treating various diseases, including cancer and neurodegenerative disorders. Its study in these areas is crucial for discovering new treatment options and improving patient outcomes.

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

Upstream product

• 54674-99-6 5-methyl-quinoline-2,4-diol 
• 153749-71-4 2,4-dichloro-5-methyl quinoline 
• 7647-01-0 hydrogenchloride 
• 56-81-5 glycerol 
• 108-44-1 1-amino-3-methylbenzene 
• 106-95-6 allyl bromide 
• 588-04-5 3,3'-dimethylazobenzene 
• 1122-62-9 2-acetylpyridine 
• 4964-71-0 5-bromoquinoline 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 58960-02-4 5-methyl-1,2,3,4-tetrahydroquinoline 
• 607-34-1 5-nitroquinoline 
• 823-96-1 Trimethylboroxine 
• 74-88-4 methyl iodide 

Downstream Products

• 22934-41-4 quinoline-5-carbaldehyde 
• 7250-53-5 quinoline-5-carboxylic acid 
• 4053-33-2 2-Hydroxy-4-methylquinoline 
• 500595-66-4 5-methyl-2-phenylquinoline 
• 1497411-41-2 C₂₀H₂₁NO₂ 
• 4053-33-2 5-methylquinolin-2-(1H)-one 
• 58960-02-4 5-methyl-1,2,3,4-tetrahydroquinoline 
• 11139-62-1 2-phenyl-quinoline-5-carboxylic acid 
• 85656-77-5 2,4,6-Trimethyl-benzenesulfonate1-amino-8-formylamino-5-methyl-quinolinium; 
• 85656-64-0 5-methyl-8-aminoquinoline 

Relevant articles and documents

Transition metal eight-coordination. IV. Tetrakis(5,7-disubstituted-8-quinolinolato)tungsten(V) salts

Violet, paramagnetic [WQ4]+ ions have been synthesized by a variety of methods and appear to be the first complexes of tungsten(V) possessing four chelate ligands. The 5,7-dichloro-8-quinolinol derivative has been synthesized by the reaction of either K3W2Cl9 or W(CO)6 with excess ligand at elevated temperatures for extended time periods or by treating the corresponding tungsten(IV) inner complex with Cl2, Br2, or HClO4 at room temperature or with additional ligand at elevated temperatures. The 7-bromo-5-methyl-8-quinolinol-tungsten(V) species is rapidly produced in the melt reaction of the ligand with W(CO)6. The [WQ4]X salts, where X- = Cl-, Br-, ClO4-, or Q-, disproportionate in alcoholic or aqueous KOH to WQ4 and tungsten(VI). Electronic transitions of the [WQ4] species consist of several bands in the near-infrared and visible region in addition to the normal ligand spectral transitions. A magnetic moment of 1.7 BM, a 〈g〉 value of 1.872, and a 183W hyperfine splitting of 85 G were observed for the dichloro derivative at room temperature. Low-temperature electron spin resonance spectra exhibit three anisotropic g values indicative of isomerization from the D2d-mmmm isomer found for a related 5-bromo-8-quinolinol-tungsten(IV) chelate.1a.

Using Data Science To Guide Aryl Bromide Substrate Scope Analysis in a Ni/Photoredox-Catalyzed Cross-Coupling with Acetals as Alcohol-Derived Radical Sources

Ni/photoredox catalysis has emerged as a powerful platform for C(sp2)–C(sp3) bond formation. While many of these methods typically employ aryl bromides as the C(sp2) coupling partner, a variety of aliphatic radical sources have been investigated. In principle, these reactions enable access to the same product scaffolds, but it can be hard to discern which method to employ because nonstandardized sets of aryl bromides are used in scope evaluation. Herein, we report a Ni/photoredox-catalyzed (deutero)methylation and alkylation of aryl halides where benzaldehyde di(alkyl) acetals serve as alcohol-derived radical sources. Reaction development, mechanistic studies, and late-stage derivatization of a biologically relevant aryl chloride, fenofibrate, are presented. Then, we describe the integration of data science techniques, including DFT featurization, dimensionality reduction, and hierarchical clustering, to delineate a diverse and succinct collection of aryl bromides that is representative of the chemical space of the substrate class. By superimposing scope examples from published Ni/photoredox methods on this same chemical space, we identify areas of sparse coverage and high versus low average yields, enabling comparisons between prior art and this new method. Additionally, we demonstrate that the systematically selected scope of aryl bromides can be used to quantify population-wide reactivity trends and reveal sources of possible functional group incompatibility with supervised machine learning.

Catalytic Aerobic Dehydrogenatin of N-Heterocycles by N-Hydoxyphthalimide

Catalytic methods for the aerobic dehydrogenation of N-heterocycles are reported. In most cases, indoles are accessed efficiently from indolines using catalytic N-hydroxyphthalimide (NHPI) as the sole additive under air. Further studies revealed an improved catalytic system of NHPI and copper for the preparation of other heteroaromatics, for example quinolines. (Figure presented.).

Method for preparation of quinoline compounds

The invention discloses a green preparation method of quinoline compounds. According to the method, cheap and easily available copper salt and N-hydroxyphthalimide are used as catalysts, oxygen is used as an oxidizing agent, oxidation of tetrahydroquinoline compounds is performed in an organic solvent, and synthesis of quinoline compounds is realized. The method has the advantages of simple reaction operation, low reaction cost, high yield, low metal pollution and the like.

A methylation platform of unconventional inert aryl electrophiles: Trimethylboroxine as a universal methylating reagent

Methylation is one of the most fundamental conversions in medicinal and material chemistry. Extension of substrate types from aromatic halides to other unconventional aromatic electrophiles is a highly important yet challenging task in catalytic methylation. Disclosed herein is a series of transition metal-catalyzed methylations of unconventional inert aryl electrophiles using trimethylboroxine (TMB) as the methylating reagent. This transformation features a broad substrate type, including nitroarenes, benzoic amides, benzoic esters, aryl cyanides, phenol ethers, aryl pivalates and aryl fluorides. Another important merit of this work is that these widespread "inert"functionalities are capable of serving as directing or activating groups for selective functionalization of aromatic rings before methylation, which greatly expands the connotation of methylation chemistry.

Pd-Catalyzed Alkylation of (Iso)quinolines and Arenes: 2-Acylpyridine Compounds as Alkylation Reagents

The first Pd-catalyzed alkylation of (iso)quinolines and arenes is reported. The readily available and bench-stable 2-acylpyridine compounds were used as an alkylation reagent to form the structurally versatile alkylated (iso)quinolines and arenes. The method affords a convenient pathway for the introduction of alkyl groups into organic molecules.

Enantioselective Intermolecular [2 + 2] Photocycloaddition Reactions of 2(1H)-Quinolones Induced by Visible Light Irradiation

In the presence of a chiral thioxanthone catalyst (10 mol %) the title compounds underwent a clean intermolecular [2 + 2] photocycloaddition with electron-deficient olefins at λ = 419 nm. The reactions not only proceeded with excellent regio- and diastereoselectivity but also delivered the respective cyclobutane products with significant enantiomeric excess (up to 95% ee). Key to the success of the reactions is a two-point hydrogen bonding between quinolone and catalyst enabling efficient energy transfer and high enantioface differentiation. Preliminary work indicated that solar irradiation can be used for this process and that the substrate scope can be further expanded to isoquinolones.

Highly Enantioselective Direct Synthesis of Endocyclic Vicinal Diamines through Chiral Ru(diamine)-Catalyzed Hydrogenation of 2,2′-Bisquinoline Derivatives

An asymmetric hydrogenation of 2,2′-bisquinoline and bisquinoxaline derivatives, catalyzed by chiral cationic ruthenium diamine complexes, was developed. A broad range of chiral endocyclic vicinal diamines were obtained in high yields with excellent diastereo- and enantioselectivity (up to 93:7 dl/meso and >99 % ee). These chiral diamines could be easily transformed into a new class of chiral N-heterocyclic carbenes (NHCs), which are important but difficult to access.

Copper-Promoted Tandem Reaction of Azobenzenes with Allyl Bromides via N=N Bond Cleavage for the Regioselective Synthesis of Quinolines

A copper-promoted tandem reaction of a variety of azobenzenes and allyl bromides via N=N bond cleavage to regioselectively construct quinoline derivatives has been developed. The azobenzenes act as not only construction units but also an oxidant for quinoline formation.

Synthesis of quinolines by iron-catalyzed reaction of anilines with propane-1,3-diol

Quinoline and its derivatives were synthesized by cyclocondensation of anilines with propane-1,3-diol in 57-96% yield in the presence of iron-containing catalysts in carbon tetrachloride.