519-66-4

Basic information

• Product Name: 4-HYDROXY-1-METHYL-3-PHENYL-1,2-DIHYDROQUINOLIN-2-ONE
• Synonyms: 4-HYDROXY-1-METHYL-3-PHENYL-1,2-DIHYDROQUINOLIN-2-ONE;4-HYDROXY-1-METHYL-3-PHENYLQUINOLIN-2(1H)-ONE;AURORA KA-3971;1-Methyl-3-phenyl-4-hydroxy-1,2-dihydroquinoline-2-one;1-Methyl-3-phenyl-4-hydroxyquinoline-2(1H)-one;Arboricin;Arboricine;NSC-675808
• CAS NO: 519-66-4
• Molecular Formula: C₁₆H₁₃NO₂
• Molecular Weight: 251.28
• Mol File: 519-66-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 225-226°C
• Boiling Point: 404.5 °C at 760 mmHg
• Flash Point: 198.4 °C
• Appearance: /
• Density: 1.293 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.669
• CAS DataBase Reference: 4-HYDROXY-1-METHYL-3-PHENYL-1,2-DIHYDROQUINOLIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-1-METHYL-3-PHENYL-1,2-DIHYDROQUINOLIN-2-ONE(519-66-4)
• EPA Substance Registry System: 4-HYDROXY-1-METHYL-3-PHENYL-1,2-DIHYDROQUINOLIN-2-ONE(519-66-4)

Safety Data

• Hazard Codes: Xi
• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 519-66-4(Hazardous Substances Data)

Usage

General Description

4-Hydroxy-1-methyl-3-phenyl-1,2-dihydroquinolin-2-one is a chemical compound with a specific structure of a dihydroquinolinone. Its molecular formula is C15H13NO2 and its molecular weight is 239.27 g/mol. It is a white crystalline solid that is insoluble in water but soluble in organic solvents. 4-HYDROXY-1-METHYL-3-PHENYL-1,2-DIHYDROQUINOLIN-2-ONE has a phenolic hydroxyl group and a methyl and phenyl substituent attached to the quinolone ring, making it a potential pharmacophore for drug design and development. The biological and chemical properties of 4-hydroxy-1-methyl-3-phenyl-1,2-dihydroquinolin-2-one make it a candidate for various applications, including medical research and as a building block for the synthesis of other chemical compounds.

InChI:InChI=1/C16H13NO2/c1-17-13-10-6-5-9-12(13)15(18)14(16(17)19)11-7-3-2-4-8-11/h2-10,18H,1H3

Upstream product

• 206363-35-1 2-(methyl-phenylacetylamino)benzoic acid methyl ester 
• 10328-92-4 N-Methylisatoic anhydride 
• 101-97-3 Ethyl 2-phenylethanoate 
• 83-13-6 diethyl 2-phenylmalonate 
• 100-61-8 N-methylaniline 
• 144603-33-8 3-chloro-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 401635-58-3 3-bromo-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 342598-46-3 N-(2-benzoylphenyl)-2,2,2-trichloro-N-methylacetamide 
• 10387-40-3 potassium thioacetate 
• 521980-39-2 1-methyl-3-phenyl-2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl thiocyanate 
• 85-91-6 Methyl N-methylanthranilate 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 1859-76-3 2-(methylamino)benzophenone 
• 103-80-0 phenylacetyl chloride 

Downstream Products

• 80356-42-9 4-Amino-1-methyl-3-phenyl-chinolin-2(1H)-on 
• 83609-72-7 5-Methyl-11-phenyl-isochinolino<4,3-c>chinolin-6(5H)-on 
• 56857-90-0 4-Chloro-1-methyl-2-oxo-3-phenyl-1,2-dihydroquinoline 
• 144603-33-8 3-chloro-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 113737-84-1 3-hydroxy-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 110216-91-6 1-Methyl-3-phenyl-4-tosyloxy-2(1H)-chinolon 
• 83609-76-1 4-Benzylamino-1-methyl-3-phenyl-chinolin-2(1H)-on 
• 401635-58-3 3-bromo-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 22462-93-7 4-acetyoxy-1-methyl-3-phenyl-1H-quinolin-2-one 
• 521980-39-2 1-methyl-3-phenyl-2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl thiocyanate 
• 622404-81-3 1-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl benzoate 
• 144603-94-1 3-azido-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 477950-08-6 3-amino-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 477950-10-0 3-butylamino-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 

Relevant articles and documents

Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones

In this study, a 50-membered library of substituted 4-hydroxyquinolin-2(1H)-ones and two closely related analogues was designed, scored in-silico for drug likeness and subsequently synthesized. Thirteen derivatives, all sharing a common 3-phenyl substituent showed minimal inhibitory concentrations against Mycobacterium tuberculosis H37Ra below 10 μM and against Mycobacterium bovis AN5A below 15 μM but were inactive against faster growing mycobacterial species. None of these selected derivatives showed significant acute toxicity against MRC-5 cells or early signs of genotoxicity in the Vitotox assay at the active concentration range. The structure activity study relation provided some insight in the further favourable substitution pattern at the 4-hydroxyquinolin-2(1H)-one scaffold and finally 6-fluoro-4-hydroxy-3-phenylquinolin-2(1H)-one (38) was selected as the most promising member of the library with a MIC of 3.2 μM and a CC50 against MRC-5 of 67.4 μM.

Reaction of some 2-quinolone derivatives with phosphoryl chloride: Synthesis of novel phosphoric acid esters of 4-hydroxy-2-quinolone

3-Chloroquinoline-2,4-diones do not react with phosphoryl chloride, however, 2,4-dichloroquinolines and/or 4-chloroquinolin-2-ones are formed in the presence of N,N-dimethylaniline. Along with these compounds, small quantities of novel dihydrogen phosphates of 4-hydroxyquinolin-2-ones were isolated. We outline a simple procedure that allows for the preparation of these compounds in moderate to good yields. All compounds were characterized by 1H and 13C NMR, IR, EI-MS, and ESI-MS spectroscopy, and in select cases by 31P NMR spectroscopy.

Catalyst-controlled divergent C-H functionalization of unsymmetrical 2-aryl cyclic 1,3-dicarbonyl compounds with alkynes and alkenes

Achieving site-selective, switchable C-H functionalizations of substrates that contain several different types of reactive C-H bonds is an attractive objective to enable the generation of different products from the same starting materials. Herein, we dem