97545-52-3

Basic information

• Product Name: 4-HYDROXY-6-METHYLQUINOLINE
• Synonyms: 4-HYDROXY-6-METHYLQUINOLINE;6-methylquinolin-4(1H)-one;6-METHYL-4(1H)-QUINOLINONE;6-METHYL-QUINOLIN-4-OL
• CAS NO: 97545-52-3
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• Mol File: 97545-52-3.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-HYDROXY-6-METHYLQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-6-METHYLQUINOLINE(97545-52-3)
• EPA Substance Registry System: 4-HYDROXY-6-METHYLQUINOLINE(97545-52-3)

Safety Data

• Hazardous Substances Data: 97545-52-3(Hazardous Substances Data)

Usage

Description

4-Hydroxy-6-methylquinoline, also known as 4-HMQ, is a quinoline derivative with the molecular formula C10H9NO and a molecular weight of 159.18 g/mol. It features a hydroxyl group and a methyl group attached to the quinoline ring, contributing to its diverse chemical properties and potential applications.

Uses

Used in Fluorescent Dyes and Optical Brighteners:
4-Hydroxy-6-methylquinoline is utilized as a key component in the production of fluorescent dyes and optical brighteners. Its unique chemical structure allows for the absorption and emission of light at specific wavelengths, making it suitable for enhancing the visibility and brightness of various materials.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, 4-HMQ is employed as an intermediate in the synthesis of various drugs. Its anti-cancer and anti-microbial properties have made it a subject of interest in medical research, with potential applications in the development of new therapeutic agents.
Used in Agrochemical Applications:
4-Hydroxy-6-methylquinoline also finds use in the agrochemical sector, where it serves as a precursor for the synthesis of pesticides and other agrochemical products. Its ability to target specific pests and pathogens makes it a valuable tool in crop protection and management.
Used in Antioxidant and Anti-inflammatory Research:
Due to its demonstrated antioxidant and anti-inflammatory activities, 4-HMQ is being investigated for potential therapeutic applications in the treatment of various diseases and conditions. Its multifaceted properties suggest that it could play a role in mitigating oxidative stress and inflammation, which are implicated in numerous pathological processes.

Upstream product

• 2033-24-1 cycl-isopropylidene malonate 
• 106-49-0 p-toluidine 
• 107-31-3 Methyl formate 
• 25428-06-2 2-amino-5-methyl-acetophenone 
• 79607-24-2 6-methyl-4-carbonylquinoline-3-carboxylic acid ethyl ester 
• 19056-84-9 diethyl 2-[(p-tolylamino)methylidene]malonate 
• 624-31-7 4-tolyl iodide 
• 38560-27-9 N-(4-methylphenyl)azetidin-2-one 
• 36054-00-9 6-methyl-2,3-dihydroquinolin-4(1H)-one 
• 109-94-4 formic acid ethyl ester 
• 122-51-0 orthoformic acid triethyl ester 
• 141-82-2 malonic acid 
• 25063-44-9 2,2-Dimethyl-5-(p-tolylamino-methylene)-[1,3]dioxane-4,6-dione 

Downstream Products

• 325856-06-2 1,6-dimethylquinolin-4(1H)-one 
• 1283075-21-7 C₁₈H₁₅NO₃ 
• 18436-71-0 4-chloro-6-methylquinoline 

Relevant articles and documents

Cu(I)-Catalyzed Alkynylation of Quinolones

Herein we report the first alkynylation of quinolones with terminal alkynes under mild reaction conditions. The reaction is catalyzed by Cu(I) salts in the presence of a Lewis acid, which is essential for the reactivity of the system. The enantioselective version of this transformation has also been explored, and the methodology has been applied in the synthesis of the enantioenriched tetrahydroquinoline alkaloid cuspareine.

Synthesis of bridged benzazocines and benzoxocines by a titanium-catalyzed double-reductive umpolung strategy

A sequence of two titanium(III)-catalyzed reductive umpolung reactions is reported that allows the rapid construction of benzazo- and benzoxozine building blocks. The first step is a reductive cross-coupling of quinolones or chromones with Michael acceptors. This reaction proceeds with complete syn-selectivity for the quinolone functionalization while the anti-diastereomers are obtained as the major products from chromones. With different reaction conditions, the stereochemical outcome can be altered to afford the syn-chromanone products as well. A subsequent reductive ketyl radical cyclization forges the tricyclic title compounds in good yields. A stereochemical model explaining the observed stereoselectivities is provided and the product configurations were unambiguously verified by X-ray analyses and 2D NMR spectroscopic experiments.

Synthesis of 2,3-dihydro-4(1H)-quinolones and the corresponding 4(1H)-quinolones via low-temperature fries rearrangement of N-arylazetidin-2- ones

N-Arylazetidin-2-ones of the general form 1, which are readily prepared by GoldbergBuchwald-type copper-catalyzed coupling of N-unsubstituted azetidin-2-ones with the relevant aryl halide or using Mitsunobu cyclization processes, undergo smooth Fries-rearrangement in triflic acid at 018°C to give the isomeric 2,3-dihydro-4(1H)-quinolones (2). Dehydrogenation of the latter compounds using 10% Pd on C in 1.0M aqueous sodium hydroxide/propan-2-ol mixtures at ca. 82°C provides the corresponding 4(1H)-quinolones (3).