1677-44-7

Basic information

• Product Name: 2-hydroxy-6-methyl-1H-quinolin-4-one
• Synonyms: 2-hydroxy-6-methyl-1H-quinolin-4-one;4,6-Dihydroxy-2-methylquinoline;6-Methyl-2,4-dihydroxyquinoline;4-Hydroxy-6-methyl-2-quinolone;6-Methylquinoline-2,4-diol;4-Hydroxy-6-methyl-1H-quinolin-2-one
• CAS NO: 1677-44-7
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• Mol File: 1677-44-7.mol
• Article Data: 18

Chemical Properties

• Melting Point: 342 ºC
• Boiling Point: 329.9°Cat760mmHg
• Flash Point: 153.3°C
• Appearance: /
• Density: 1.313
• Vapor Pressure: 6.91E-05mmHg at 25°C
• Refractive Index: 1.637
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 2-hydroxy-6-methyl-1H-quinolin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-6-methyl-1H-quinolin-4-one(1677-44-7)
• EPA Substance Registry System: 2-hydroxy-6-methyl-1H-quinolin-4-one(1677-44-7)

Safety Data

• Hazardous Substances Data: 1677-44-7(Hazardous Substances Data)

Usage

General Description

2-hydroxy-6-methyl-1H-quinolin-4-one, also known as quinolin-4-ol, is a chemical compound with the molecular formula C10H9NO2. It is a derivative of quinoline and contains a hydroxyl group and a methyl group on the quinoline ring. 2-hydroxy-6-methyl-1H-quinolin-4-one is a yellow crystalline solid and is used as a starting material in the synthesis of pharmaceuticals and organic compounds. It has also been explored for its potential antimicrobial and antioxidant properties, making it a valuable molecule in the development of new drugs and functional materials. Additionally, 2-hydroxy-6-methyl-1H-quinolin-4-one has been studied for its potential role in the treatment of various diseases and as a fluorescent label for biological imaging.

InChI:InChI=1/C10H9NO2/c1-6-2-3-8-7(4-6)9(12)5-10(13)11-8/h2-5H,1H3,(H2,11,12,13)

Upstream product

• 141-82-2 malonic acid 
• 106-49-0 p-toluidine 
• 189274-63-3 7-Methyl-oxazolo[3,2-a]quinoline-1,2,5-trione 
• 124-38-9 carbon dioxide 
• 215589-37-0 2-ethynyl-4-methylaniline 
• 105-53-3 diethyl malonate 
• 95262-01-4 N-p-tolyl-malonamic acid 
• 5469-94-3 N,N'-bis(4-methylphenyl)malonamide 
• 621-10-3 N,N'-diphenylmalonamide 
• 67081-68-9 2-acetamido-5-methylbenzoic acid 

Downstream Products

• 102878-18-2 2,4-dichloro-6-methyl-quinoline 
• 138964-62-2 6-Methyl-3-[1-phenyl-2-thiocyanato-eth-(Z)-ylidene]-1H-quinoline-2,4-dione 
• 161152-26-7 3--4-hydroxy-6-methyl-2(1H)-quinolone 
• 1346462-41-6 ethyl 2-amino-4-(2-chlorophenyl)-5,6-dihydro-9-methyl-5-oxo-4H-pyrano[3,2-c]quinoline-3-carboxylate 
• 1346462-42-7 ethyl 2-amino-4-(3-chlorophenyl)-5,6-dihydro-9-methyl-5-oxo-4H-pyrano[3,2-c]quinoline-3-carboxylate 
• 1346462-43-8 ethyl 2-amino-4-(4-chlorophenyl)-5,6-dihydro-9-methyl-5-oxo-4H-pyrano[3,2-c]quinoline-3-carboxylate 
• 1346462-44-9 ethyl 2-amino-5,6-dihydro-4-(4-hydroxyphenyl)-9-methyl-5-oxo-4H-pyrano[3,2-c]quinoline-3-carboxylate 
• 1346462-45-0 ethyl 2-amino-5,6-dihydro-9-methyl-4-(3-nitrophenyl)-5-oxo-4H-pyrano[3,2-c]quinoline-3-carboxylate 
• 384363-16-0 ethyl 2-amino-5,6-dihydro-9-methyl-5-oxo-4-phenyl-4H-pyrano[3,2-c]quinoline-3-carboxylate 

Relevant articles and documents

Synthesis and colon anticancer activity of some novel thiazole/-2-quinolone derivatives

We direct for the synthesis of 1,6,7-trisubstituted-4-phenylthiazol-2(3H)-ylidene)hydrazono)methyl)quinolin-2-one derivatives by the reaction of corresponding thiosemicarbazone derived by 2-quinolone derivatives with 2-bromoacetophenones in presence of triethylamine at room temperature. The mechanism of the formed products was discussed. The structure of the obtained products was fully characterized using different spectral techniques including infrared (IR), nuclear magnetic resonance (NMR), and mass spectrometry (MS) together with elemental analyses. The new synthesized compounds showed a moderate colon anticancer activity.

Method for preparing 4-hydroxyquinolin-2(1H)-one compound

The invention discloses a method for preparing a 4-hydroxyquinolin-2(1H)-one compound, which comprises the following steps of: reacting 2-ethynylaniline as shown in a formula (1) and carbon dioxide which are used as raw materials in an ionic liquid in the presence of a silver salt catalyst to obtain the 4-hydroxyquinoline-2 (1H)-one compound as shown in a formula (II). The reaction equation is shown in the specification. When the method disclosed by the invention is applied to the reaction for preparing the 4-hydroxyquinolin-2(1H)-one compound, the reaction conditions are relatively mild, the dosage of the silver salt catalyst is small, the separation and purification process of the product is relatively simple, the product yield is high, and the application range of a substrate is wide.

Identification and molecular modeling of new quinolin-2-one thiosemicarbazide scaffold with antimicrobial urease inhibitory activity

Abstract: A new series of 6-substituted quinolin-2-one thiosemicarbazides 6a–j has been synthesized. The structure of the target compounds was proved by different spectroscopic and elemental analyses. All the designed final compounds were evaluated for their in vitro activity against the urease-producing R. mucilaginosa and Proteus mirabilis bacteria as fungal and bacterial pathogens, respectively. Moreover, all compounds were in vitro tested as potential urease inhibitors using the cup-plate diffusion method. Compounds 6a and 6b were the most active with (IC50 = 0.58 ± 0.15 and 0.43 ± 0.09?μM), respectively, in comparison with lead compound I (IC50 = 1.13 ± 0.00?μM). Also, the designed compounds were docked into urease proteins (ID: 3LA4 and ID: 4UBP) using Open Eye software to understand correctly about ligand–receptor interactions. The docking results revealed that the designed compounds can interact with the active site of the enzyme through multiple strong hydrogen bonds. Moreover, rapid overlay of chemical structures’ analysis was described to understand the 3D QSAR of synthesized compounds as urease inhibitors. The results emphasize the importance of polar thiosemicarbazide directly linked to 6-substituted quinolone moieties as promising antimicrobial urease inhibitors. Graphic abstract: [Figure not available: see fulltext.]