606-43-9

Basic information

• Product Name: 1-METHYL-2-QUINOLINONE
• Synonyms: 1-Methyl-1,2-dihydroquinolin-2-one;1-Methyl-1H-quinolin-2-one;1-methyl-2(1h)-quinolinon;1-Methyl-2(1H)-quinolone;1-Methyl-2-quinolone;1-Methylcarbostyril;2(1H)-Quinolinone,1-methyl-;Carbostyril, 1-methyl-
• CAS NO: 606-43-9
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• EINECS: -0
• Mol File: 606-43-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 74-76°C
• Boiling Point: 284.68°C (rough estimate)
• Flash Point: 106.8 °C
• Appearance: /
• Density: 1.1202 (rough estimate)
• Vapor Pressure: 0.0255mmHg at 25°C
• Refractive Index: 1.6070 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.49±0.20(Predicted)
• BRN: 121318
• CAS DataBase Reference: 1-METHYL-2-QUINOLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-2-QUINOLINONE(606-43-9)
• EPA Substance Registry System: 1-METHYL-2-QUINOLINONE(606-43-9)

Safety Data

• Safety Statements: 22-24/25
• TSCA: Yes
• Hazardous Substances Data: 606-43-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 21, p. 107, 1984 DOI: 10.1002/jhet.5570210123Synthetic Communications, 25, p. 2999, 1995 DOI: 10.1080/00397919508011432

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

Upstream product

• 2525-21-5 N-methylquinoline hydrochloride 
• 5332-24-1 3-bromoquinoline 
• 3638-64-0 1-nitroethylene 
• 3558-24-5 1-methyl-2-phenyl-1H-indole 
• 875-79-6 1,2-dimethylindole 
• 85749-93-5 3-bromo-1,2-dihydro-1-methylquinoline 
• 3947-76-0 N-methylquinolinium iodide 
• 132363-86-1 1-methyl-2-trichloromethyl-1,2-dihydroquinoline 
• 67-66-3 chloroform 

Downstream Products

• 612-62-4 2-Chloroquinoline 
• 16021-60-6 1-Methyl-1,2-dihydroquinoline 
• 4800-27-5 1-methylquinoline-2(1H)-thione 
• 491-34-9 N-methyl-1,2,3,4-tetrahydroquinoline 
• 51594-53-7 2-(4-dimethylamino-phenyl)-1-methyl-quinolinium; chloride 
• 74-89-5 methylamine 
• 2859-29-2 1-methyl-3-phenylquinolin-2(1H)-one 
• 91-64-5 coumarin 
• 698975-01-8 4-chloro-N-(quinolin-2-yl)benzamide 
• 16717-25-2 6-bromo-1-methylquinoline-2(1H)-one 

Relevant articles and documents

Cyclobutane-cleavage of anti-head-to-head coumarin and quinolinone homo- and cross-dimers via single- and two-photon-absorption photochemistry

The light-driven cleavage of cyclobutane containing systems via [2 + 2] cycloreversion, such as di-coumarin, is an important yet poorly investigated photochemical reaction. Its applications can be found in smart crosslinking polymers or light-activated drug release. We report the increased cleavage efficiencies of the coumarins lactam analog quinolinone for single-photon as well as two-photon-absorption experiments. To investigate the structure-function relationship of the molecular substitution pattern and its influence on the photoactivity, a coumarin-quinolinone cross-dimer was synthesized and investigated towards its cleavage efficiencies in single-photon as well as two-photon photocleavage. The cross-dimer shows a lower cleavage efficiency than both homo-dimers. The presented results are of interest, e.g., for applications utilizing highly efficient cleavage reactions in symmetric or asymmetric molecular frameworks.

Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones

3-Substituted 2-quinolones are obtained via a novel metal-free transannulation reaction of 2-nitroolefins with 2-substituted indoles in polyphosphoric acid. This acid-mediated cascade transformation operates via the ANRORC (Addition of Nucleophile, Ring Opening, and Ring Closure) mechanism and can be used in combination with the Fisher indole synthesis to offer a practical three-component hetero-annulation approach to 2-quinolones from arylhydrazines, 2-nitroalkenes, and acetophenone. An alternative entry to this chemistry employing the alkylation of electron-rich arenes and hetarenes with 1-(2-indolyl)-2-nitroalkene has also been demonstrated.

Synthesis and reactivities of 1-methyl-2-trichloromethyl-1,2-dihydroquinolines

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