130820-63-2

Basic information

• Product Name: 2-(4-BROMOPHENYL)-2,3-DIHYDRO-4(1H)-QUINOLINONE
• Synonyms: 2-(4-BROMOPHENYL)-2,3-DIHYDRO-4(1H)-QUINOLINONE;2-(4-bromophenyl)-2,3-dihydroquinolin-4(1H)-one;2-(4-Bromo-phenyl)-2,3-dihydro-1H-quinolin-4-one
• CAS NO: 130820-63-2
• Molecular Formula: C₁₅H₁₂BrNO
• Molecular Weight: 302.17
• Mol File: 130820-63-2.mol

Chemical Properties

• Boiling Point: 450°C at 760 mmHg
• Flash Point: 225.9°C
• Appearance: /
• Density: 1.444g/cm³
• Vapor Pressure: 2.74E-08mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(4-BROMOPHENYL)-2,3-DIHYDRO-4(1H)-QUINOLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-BROMOPHENYL)-2,3-DIHYDRO-4(1H)-QUINOLINONE(130820-63-2)
• EPA Substance Registry System: 2-(4-BROMOPHENYL)-2,3-DIHYDRO-4(1H)-QUINOLINONE(130820-63-2)

Safety Data

• Hazardous Substances Data: 130820-63-2(Hazardous Substances Data)

Usage

Structure

Quinolinone derivative with a bromophenyl group attached to the 2-position of the quinolinone ring

Usage

Building block for the synthesis of various bioactive molecules in the pharmaceutical industry

Biological activities

Anti-inflammatory and anticancer properties

Enzyme inhibition

Moderate inhibitory activity against certain enzymes

Value in research

Valuable chemical for drug discovery and development due to its diverse biological activities

InChI:InChI=1/C15H12BrNO/c16-11-7-5-10(6-8-11)14-9-15(18)12-3-1-2-4-13(12)17-14/h1-8,14,17H,9H2

Upstream product

• 144221-09-0 (E)-1-(2'-aminophenyl)-3-(4-bromophenyl)-2-propen-1-one 
• 551-93-9 2-aminoacetophenone 
• 1122-91-4 4-bromo-benzaldehyde 
• 195073-95-1 1-(2-aminophenyl)-3-(4-bromophenyl)prop-2-en-1-one 
• 577-59-3 2-acetylnitrobenzene 

Downstream Products

• 149191-92-4 2-(4-Bromo-phenyl)-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one 
• 1133158-61-8 6-chloro-2-(4'-bromophenyl)-2,3-dihydro-4(1H)-quinolone 
• 1171953-09-5 2-(4-bromophenyl)-3-((pyridin-4-yl)methyl)quinolin-4(1H)-one 
• 1097957-52-2 1-acetyl-2-(4-bromophenyl)-2,3-dihydroquinolin-4(1H)-one 

Relevant articles and documents

Organometallic titanocene complex as highly efficient bifunctional catalyst for intramolecular Mannich reaction

Bifunctional catalysts bearing two catalytic sites, Lewis acidic organometallic titanocene and Br?nsted acidic COOH, have been assembled in situ from Cp2TiCl2 with carboxylic acid ligands, showing high catalytic activity over an intramolecular Mannich reaction towards synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones. The determination of the bifunctional catalyst Cp2Ti(C8H4NO6)2 was elucidated by single X-ray HR-MS and investigation of catalytic behavior. In particular, masking the Br?nsted acidic COOH catalytic site with dormant COOMe lowered the reaction yield greatly, indicating that two catalytic sites work together to maintain high catalytic efficiency.

Zirconyl Nitrate as an Efficient Catalyst for Facile Synthesis of 2-Aryl-2,3-dihydroquinolin-4(1 H)-one Derivatives in Aqueous Medium

A simple, green, and efficient method is introduced for the synthesis of 2-aryl-2,3-dihydroquinolin-4(1 H)-ones under mild reaction conditions with improved yields by intramolecular cyclization of o -aminochalcones with zirconyl nitrate [Zn(O)(NO 3/

Titanocene complex with oxygen-containing carboxylic acid as ligand as well as preparation method and application of titanocene complex

The invention discloses a titanocene complex with oxygen-containing carboxylic acid as well as a preparation method and an application of the titanocene complex. The structural formula of the complexis shown in the description. The titanocene complex is p

2-aryl-2,3-dihydro-4(1H)-quinolinone semicarbazone compound and application thereof

The invention relates to the field of medicine technology, and a series of novel 2-aryl-2,3-dihydrogen-4(1H)-quinolinone semicarbazone derivatives (I) and pharmaceutically acceptable salts, solvates,optical isomers or polymorphs are designed and synthesized. The derivative (I) and its pharmaceutically acceptable salt, solvate, optical isomer or polymorph can be mixed as an active ingredient witha pharmaceutically acceptable carrier to prepare a pharmaceutical composition. A double dilution method is used for test of the antifungal activity of the derivative (I) and its pharmaceutically acceptable salt, solvate, optical isomer or polymorph, and the results show that the derivative has stronger killing effect on clinically common pathogenic fungi, and is expected to overcome the defects oflarge toxic and side effects, easy generation of drug resistance of azole antifungal medicines which are widely used clinically. The specific formula is shown in the description.

Synthesis, molecular modeling and biological evaluation of aza-flavanones as α-glucosidase inhibitors

An efficient acid catalyzed methodology has been employed to synthesize a variety of aza-flavanones and their α-glucosidase inhibitory activity is evaluated using acarbose, miglitol and voglibose as reference standards. Molecular modeling studies were per

A general and efficient synthesis of 5,6-dihydrodibenzo[b,h][1,6]naphthyridine derivatives

A two-step procedure for the synthesis of dihydrodibenzonaphthyridine derivatives from benzaldehydes and 2-aminoacetophenones, proceeding through a substituted dihydroquinolone intermediate, is described. The synthetic protocol allows for a versatile and robust coupling method between a range of 2-aminoacetophenones or 2-aminobenzophenones and a selection of substituted dihydroquinolones.

[C8dabco]Br: a mild and convenient catalyst for intramolecular cyclization of 2-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones

[Figure not available: see fulltext.] A new and convenient synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones has been described using the intramolecular cyclization of 2-aminochalcones catalyzed by 1-octyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide ([Cs

Mild and Efficient Silver(I) Triflate Catalyzed Synthesis of 2-Aryl-2,3-dihydroquinolin-4(1 H)-ones, and Their Antioxidant Activities

Biologically interesting 2-aryl-2,3-dihydroquinolin-4(1H)-ones were synthesized using a mild and efficient one-pot procedure starting from o-aminoacetophenones and aromatic aldehydes in the presence of silver(I) triflate. This synthetic protocol provides rapid access to a variety of 2-aryl-2,3-dihydroquinolin-4(1H)-ones. This technique has several advantages, such as the use of easily available starting materials, the efficiency of the catalyst, a simple operation, and tolerance of a wide range of functionality in the aldehydes. Screening of the synthesized compounds for their antioxidant properties revealed that two compounds (with EC50 = 15.42 μM and 15.16 μM) exhibit a potent free-radical scavenging ability towards TEAC free radicals compared to the standard, Trolox.

Silica supported-double metal cyanides (DMCs): A green and highly efficient catalytic protocol for isomerisation of 2′-hydroxychalcones to flavanones

Four different double metal cyanides (NiHCFe, CrHCFe, MnHCFe and ZnHCFe) were synthesized, followed by adsorbed on silica gel and used as Lewis acid catalyst in the isomerisation of substituted 2′-hydroxychalcones to flavanones under solvent-free (dry) condition. Optimization of the reaction condition, temperature effects, DMC catalysts loading and re-useable catalytic activity were further studied during the reaction. Among these catalysts, NiHCFe at 35 mol% loading gave excellent yield (90%) at 100 C temperature in 1.15 h. Catalyst (NiHCFe) easily recovered and re-used six times without much loss of its catalytic activity which gave 80-85% product yields each time. However, these DMCs were failed to give product in the solution phase even prolonging the reaction time at reflux temperature. Similarly, isomerization of substituted 2′-aminochalcones gave 2-5% yields either in solution phase or under solvent-free condition.

An efficient and rapid intramolecular aza-Michael addition of 2′-aminochalcones using ionic liquids as recyclable reaction media

A new, convenient, and efficient method for the intramolecular aza-Michael addition reaction of 2′-aminochalcones is developed using 1-n-butyl-3-methylimidazolium tetrafluoroborate as the solvent and catalyst. The ionic liquid is successfully regenerated and reused.