590372-17-1

Basic information

• Product Name: 2-BROMO-4-(TRIFLUOROMETHYL)QUINOLINE
• Synonyms: 2-BROMO-4-(TRIFLUOROMETHYL)QUINOLINE;Quinoline,2-broMo-4-(trifluoroMethyl)-;2-Bromo-4-(trifluoromethyl)-1-azanaphthalene
• CAS NO: 590372-17-1
• Molecular Formula: C10H5BrF3N
• Molecular Weight: 276.05
• Product Categories: Quinoline series;Quinolines, Isoquinolines & Quinoxalines;Halides;Quinolines, Isoquinolines & Quinoxalines
• Mol File: 590372-17-1.mol

Chemical Properties

• Melting Point: 56-57 ºC
• Boiling Point: 292 ºC
• Flash Point: 130 ºC
• Appearance: /
• Density: 1.658
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.573
• PKA: -1.94±0.50(Predicted)
• CAS DataBase Reference: 2-BROMO-4-(TRIFLUOROMETHYL)QUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-4-(TRIFLUOROMETHYL)QUINOLINE(590372-17-1)
• EPA Substance Registry System: 2-BROMO-4-(TRIFLUOROMETHYL)QUINOLINE(590372-17-1)

Safety Data

• Hazardous Substances Data: 590372-17-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-BROMO-4-(TRIFLUOROMETHYL)QUINOLINE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
2-BROMO-4-(TRIFLUOROMETHYL)QUINOLINE is utilized as a building block in the creation of agrochemicals, playing a role in the development of new pesticides or other agricultural chemicals to improve crop protection and yield.
Used in Medicinal Chemistry Research:
2-BROMO-4-(TRIFLUOROMETHYL)QUINOLINE is employed as a research chemical in medicinal chemistry, aiding scientists in exploring its properties and potential uses in drug discovery and design.
Used in Antimicrobial and Antifungal Applications:
2-BROMO-4-(TRIFLUOROMETHYL)QUINOLINE has been studied for its potential as an antimicrobial and antifungal agent, indicating its use in the development of treatments for microbial and fungal infections.

InChI:InChI=1/C10H5BrF3N/c11-9-5-7(10(12,13)14)6-3-1-2-4-8(6)15-9/h1-5H

Upstream product

• 25199-84-2 4-(trifluoromethyl)quinolin-2(1H)-one 
• 62-53-3 aniline 

Downstream Products

• 590372-20-6 2-bromo-4-trifluoromethyl-3-quinolinecarboxylic acid 
• 25199-77-3 4-(trifluoromethyl)quinoline 
• 155495-82-2 4-trifluoromethyl-3-quinolinecarboxylic acid 

Relevant articles and documents

On the mechanism of the palladium-catalyzed tert-butylhydroperoxide- mediated wacker-type oxidation of alkenes using quinoline-2-oxazoline ligands

The mechanism of the tert-butylhydroperoxide-mediated, Pd(Quinox)-catalyzed Wacker-type oxidation was investigated to evaluate the hypothesis that a selective catalyst-controlled oxidation could be achieved by rendering the palladium coordinatively saturated using a bidentate amine ligand. The unique role of the Quinox ligand framework was probed via systematic ligand modifications. The modified ligands were evaluated through quantitative Hammett analysis, which supports a push-pull relationship between the electronically asymmetric quinoline and oxazoline ligand modules.

4-(Trifluoromethyl)quinoline derivatives

Under carefully controlled conditions, ethyl 4,4,4-trifluoroacetoacetate (ethyl 4,4,4-trifluoro-3-oxobutanoate) can be condensed with anilines and subsequently cyclized to give 4-trifluoromethyl-2-quinolinones 1 although only in poor yield. Heating these products with phosphoryl tribromide affords 2-bromo-4-(trifluoromethyl)quinolines 2 which can be converted into 4-(trifluoromethyl)quinolines 3 by reduction, 4-trifluoromethyl-2-quinolinecarboxylic acids 4 by permutational halogen/metal exchange followed by carboxylation, and 2-bromo-4-trifluoromethyl-3-quinolinecarboxylic acids 5 by consecutive treatment with lithium diisopropylamide and dry ice. Debromination of acids 5 makes 4-trifluoromethyl-3-quinolinecarboxylic acids 6 available. As at any time 2-trifluoromethyl-4-quinolinones 9 may form instead of the expected isomers 1, the structures have to be assigned on the basis of unequivocal NMR spectral criteria. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.