23432-40-8

Basic information

• Product Name: 4-HYDROXY-6-METHYLQUINOLINE
• Synonyms: 4-HYDROXY-6-METHYLQUINOLINE;6-METHYL-4(1H)-QUINOLINONE;6-METHYL-QUINOLIN-4-OL;6-Methyl-4(1H)-quinolinone([97545-52-3]);Nsc82351;6-methyl-4-quinolinol(SALTDATA: FREE);6-Methyl-4-quinolinol
• CAS NO: 23432-40-8
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• Mol File: 23432-40-8.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 290.3°Cat760mmHg
• Flash Point: 131.4°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 0.00208mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-HYDROXY-6-METHYLQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-6-METHYLQUINOLINE(23432-40-8)
• EPA Substance Registry System: 4-HYDROXY-6-METHYLQUINOLINE(23432-40-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 23432-40-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 2772, 1984 DOI: 10.1021/jo00189a025

InChI:InChI=1/C10H9NO/c1-7-2-3-9-8(6-7)10(12)4-5-11-9/h2-6H,1H3,(H,11,12)

Upstream product

• 35973-18-3 4-hydroxy-6-methyl-quinoline-3-carboxylic acid 
• 25063-44-9 2,2-Dimethyl-5-(p-tolylamino-methylene)-[1,3]dioxane-4,6-dione 
• 85418-82-2 ethyl 4-hydroxy-6-methylquinoline-3-carboxylate 
• 106-49-0 p-toluidine 
• 19056-84-9 diethyl 2-[(p-tolylamino)methylidene]malonate 
• 180624-14-0 4-methyl-2-[2-(trimethylsilyl)ethynyl]aniline 
• 215589-37-0 2-ethynyl-4-methylaniline 
• 29289-13-2 2-iodo-4-methylaniline 
• 141-82-2 malonic acid 
• 122-51-0 orthoformic acid triethyl ester 
• 25428-06-2 2-amino-5-methyl-acetophenone 
• 109-94-4 formic acid ethyl ester 
• 36054-00-9 6-methyl-2,3-dihydroquinolin-4(1H)-one 
• 38560-27-9 N-(4-methylphenyl)azetidin-2-one 

Downstream Products

• 18436-71-0 4-chloro-6-methylquinoline 
• 91-62-3 6-methylquinoline 
• 325856-06-2 1,6-dimethylquinolin-4(1H)-one 
• 1621082-95-8 4-methyl-N-(4-methyl-2-{1-[(4-methylphenyl)sulfonyl]-1Hpyrazol-3-yl}phenyl)benzenesulfonamide 
• 1082748-37-5 C₁₀H₁₁N₃ 
• 1283075-21-7 C₁₈H₁₅NO₃ 

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.

Copper-Catalyzed Chemoselective Cyclization Reaction of 2-Isocyanoacetophenone: Synthesis of 4-Hydroxyquinoline Compounds

A copper-catalyzed intramolecular cyclization reaction of 2-isocyanoacetophenone derivatives to afford 4-hydroxyquinolines chemoselectively is described. The transformation proceeds through enol tautomerism and a subsequent C-C bond formation. Compared to previous methods, this study provides a new protocol for the construction of 4-hydroxyquinoline compounds from functionalized isocyanides under mild conditions.

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.