939-16-2

Basic information

• Product Name: 3-BROMOQUINOLIN-2(1H)-ONE
• Synonyms: 3-BROMOQUINOLIN-2(1H)-ONE;3-Bromo-1H-quinolin-2-one;3-bromocarbostyril;2(1H)-Quinolinone, 3-bromo-;3-bromo-2-quinolinol(SALTDATA: FREE);3-broMo-1,2-dihydroquinolin-2-one;3-Bromo-2-hydroxyquinoline;3-bromo-2-quinolinol
• CAS NO: 939-16-2
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05404
• Mol File: 939-16-2.mol
• Article Data: 15

Chemical Properties

• Melting Point: 260-265°C
• Boiling Point: 395.2 °C at 760 mmHg
• Flash Point: 192.8 °C
• Appearance: /
• Density: 1.666 g/cm³
• Vapor Pressure: 1.87E-06mmHg at 25°C
• Refractive Index: 1.654
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.10±0.70(Predicted)
• CAS DataBase Reference: 3-BROMOQUINOLIN-2(1H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMOQUINOLIN-2(1H)-ONE(939-16-2)
• EPA Substance Registry System: 3-BROMOQUINOLIN-2(1H)-ONE(939-16-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 939-16-2(Hazardous Substances Data)

Usage

General Description

3-Bromoquinolin-2(1H)-one, also known as 2-Quinolinol, 3-bromo, is a chemical compound with the molecular formula C9H5BrNO. It is primarily used in the field of organic synthesis. 3-BROMOQUINOLIN-2(1H)-ONE falls under the category of brominated heterocyclic compounds and exhibits aromaticity due to the existence of delocalized pi electrons in its structure. It is characterized by the presence of a bromo functional group, a quinolinone group, and has a hydrogen atom on its second position. The detailed properties such as toxicity, reactivity, and environmental impacts of this compound may vary and should be handled with adequate safety measures.

InChI:InChI=1/C9H6BrNO/c10-7-5-6-3-1-2-4-8(6)11-9(7)12/h1-5H,(H,11,12)

Upstream product

• 5332-24-1 3-bromoquinoline 
• 22615-00-5 3-bromoquinoline N-oxide 
• 59-31-4 2-quinolone 

Downstream Products

• 941-91-3 3-bromo-1-methylquinolin-2(1H)-one 
• 613-18-3 2,3-dichloroquinoline 
• 101870-60-4 3-bromo-2-chloro-quinoline 
• 954416-49-0 C₁₆H₁₂NOBr 
• 745018-52-4 3-[1-(5-bromopentyl)-2-oxo-1,2-dihydroquinolin-3-yl]benzonitrile 
• 745018-54-6 3-{1-[5-((2S,6R)-2,6-dimethylpiperidin-1-yl)pentyl]-2-oxo-1,2-dihydroquinolin-3-yl}benzonitrile 
• 114414-78-7 neocryptolepine 
• 197524-37-1 1-methyl-3-(o-aminophenyl)-1H-quinoline-2-one 
• 197524-35-9 2,2-Dimethyl-N-[2-(1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-phenyl]-propionamide 
• 5873-00-7 3-amino-quinoline-2-(1H)-one 
• 1245614-64-5 C₁₆H₁₂BrNO₂ 
• 80356-75-8 (E)-1-methyl-3-styrylquinolin-2-one 
• 1309690-17-2 (3-phenyloxiran-2-yl)quinolin-2(1H)-one 
• 1309690-18-3 1-methyl-(3-phenyloxiran-2-yl)quinolin-2(1H)-one 

Relevant articles and documents

Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides

Quinolin-2(1H)-ones are one of the important classes of compounds due to their prevalence in natural products and in pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides. This reagent free highly atom economical photocatalytic method, with low catalyst loading, high yield and no undesirable by-product, provides an efficient greener alternative to all conventional synthesis reported to date. The robustness of the methodology has been successfully demonstrated with easy scaling up to the gram scale.

Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions

An enantioselective sulfimidation of 3-thiosubstituted 2-quinolones and 2-pyridones was achieved with a stoichiometric nitrene source (PhI=NNs) and a silver-based catalyst system. Key to the success of the reaction is the use of a chiral phenanthroline ligand with a hydrogen bonding site. The enantioselectivity does not depend on the size of the two substituents at the sulfur atom but only on the binding properties of the heterocyclic lactams. A total of 21 chiral sulfimides were obtained in high yields (44–99 %) and with significant enantiomeric excess (70–99 % ee). The sulfimidation proceeds with high site-selectivity and can also be employed for the kinetic resolution of chiral sulfoxides. Mechanistic evidence suggests the intermediacy of a heteroleptic silver complex, in which the silver atom is bound to one molecule of the chiral ligand and one molecule of an achiral 1,10-phenanthroline. Support for the suggested reaction course was obtained by ESI mass spectrometry, DFT calculations, and a Hammett analysis.

Preparation method of 2-quinolinone compounds

The invention provides a preparation method of 2-quinolinone compounds. Quinoline-N-oxide compounds are served as raw materials and react in an organic solvent in the presence of zinc salt served as acatalyst and under the illumination of an xenon lamp, a series of 2-quinolinone compounds are synthesized. The preparation method provided by the invention has the following beneficial effects: as animportant nitrogen-containing heterocyclic compound, the quinolinone compounds are already applied to the fields such as medicine and important reaction intermediates and have a broad prospect in market application. According to the preparation method provided by the invention, quinoline-N-oxides are served as raw materials and react in the organic solvent in the presence of cheap metal salt served as a catalyst and in the condition of illumination, a series of 2-quinolinone compounds are synthesized; the method has the advantages of simple steps, easily available raw materials, mild reactionconditions, accordance to the principles of green chemistry and the like. The preparation method provided by the invention has relatively great use value and social and economic benefits.