32262-17-2

Basic information

• Product Name: 4-CHLORO-1-METHYL-1H-QUINOLIN-2-ONE
• Synonyms: AURORA KA-3918;4-CHLORO-1-METHYL-1,2-DIHYDROQUINOLIN-2-ONE;4-CHLORO-1-METHYL-1H-QUINOLIN-2-ONE;AKOS BBS-00003076;4-Chloro-1-methylquinolin-2(1H)-one;Nsc39972;4-Chloro-1,2-dihydro-1-methyl-2-oxoquinoline
• CAS NO: 32262-17-2
• Molecular Formula: C₁₀H₈ClNO
• Molecular Weight: 193.63
• Mol File: 32262-17-2.mol

Chemical Properties

• Melting Point: 117-119 °C
• Boiling Point: 274 °C at 760 mmHg
• Flash Point: 119.5 °C
• Appearance: /
• Density: 1.33 g/cm³
• Vapor Pressure: 0.00554mmHg at 25°C
• Refractive Index: 1.631
• PKA: -1.07±0.40(Predicted)
• CAS DataBase Reference: 4-CHLORO-1-METHYL-1H-QUINOLIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-1-METHYL-1H-QUINOLIN-2-ONE(32262-17-2)
• EPA Substance Registry System: 4-CHLORO-1-METHYL-1H-QUINOLIN-2-ONE(32262-17-2)

Safety Data

• Hazardous Substances Data: 32262-17-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H8ClNO/c1-12-9-5-3-2-4-7(9)8(11)6-10(12)13/h2-6H,1H3

Upstream product

• 1677-46-9 4-hydroxy-1-methyl-2(1H)-quinolone 
• 68-12-2 N,N-dimethyl-formamide 
• 703-61-7 2,4-dichloroquinoline 

Downstream Products

• 192633-21-9 4-hydrazino-1-methyl-2(1H)-quinolinone 
• 2584-37-4 1-methyl-4-phenyl-1H-quinolin-2-one 
• 692775-64-7 PdCl((C₆H₅)3P)2C₉H₅NCH₃O 
• 852203-12-4 3-bromo-1-methyl-4-phenylquinolin-2(1H)-one 
• 852203-14-6 6-bromo-1-methyl-4-phenylquinolin-2(1H)-one 

Relevant articles and documents

4-Aminoquinolone piperidine amides: Noncovalent inhibitors of DprE1 with long residence time and potent antimycobacterial activity

4-Aminoquinolone piperidine amides (AQs) were identified as a novel scaffold starting from a whole cell screen, with potent cidality on Mycobacterium tuberculosis (Mtb). Evaluation of the minimum inhibitory concentrations, followed by whole genome sequencing of mutants raised against AQs, identified decaprenylphosphoryl-β-d-ribose 2′-epimerase (DprE1) as the primary target responsible for the antitubercular activity. Mass spectrometry and enzyme kinetic studies indicated that AQs are noncovalent, reversible inhibitors of DprE1 with slow on rates and long residence times of ～100 min on the enzyme. In general, AQs have excellent leadlike properties and good in vitro secondary pharmacology profile. Although the scaffold started off as a single active compound with moderate potency from the whole cell screen, structure-activity relationship optimization of the scaffold led to compounds with potent DprE1 inhibition (IC50 10 nM) along with potent cellular activity (MIC = 60 nM) against Mtb.

Chemistry of Carbostyril: Part I - Oxidation Reactions of 4-Hydroxy- and 4-Hydroxy-1-methyl-2(1H)-quinolinones

4-Hydroxy-2(1H)-quinolinone (1) reacts with acetic anhydride in dimethylsulphoxide at 100 deg to afford 3-dimethylsulfonioquinoline-2,4-dionate (3) whereas 3,3'-methylenebis (4) and 2,3,4,5,1',2',3',4'-octahydro-4,2',4'-trioxospioroquinoline-2,3'-quinoline> (5) are formed when the reaction is carried out at 165-70 deg.The involvement of 4 as a precursor of 5 has been demonstrated.Probable mechanisms of their formation have been proposed.The behaviour of 4-hydroxy-1-methyl-2(1H)-quinolinone (2) towards other oxidising agents, such as HNO3, CrO3, SOCl2-DMF and p-benzoquinone has also been studied.