328956-08-7

Basic information

• Product Name: 6-Fluoro-4-(trifluoromethyl)-2(1H)-quinolinone
• Synonyms: 6-Fluoro-4-(trifluoromethyl)-2(1H)-quinolinone;6-Fluoro-4-(trifluoromethyl)quinolin-2-ol;6-Fluoro-4-(trifluoromethyl)quinolin-2-ol ,97%;6-Fluoro-2-hydroxy-4-(trifluoroMethyl)quinoline, 97%;6-Fluoro-4-(trifluoroMethyl)quinolin-2(1H)-one;6-fluoro-4-(trifluoromethyl)-1H-quinolin-2-one
• CAS NO: 328956-08-7
• Molecular Formula: C10H5F4NO
• Molecular Weight: 231.15
• Mol File: 328956-08-7.mol

Chemical Properties

• Boiling Point: 282 ºC
• Flash Point: 124 ºC
• Appearance: /
• Density: 1.468
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6-Fluoro-4-(trifluoromethyl)-2(1H)-quinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Fluoro-4-(trifluoromethyl)-2(1H)-quinolinone(328956-08-7)
• EPA Substance Registry System: 6-Fluoro-4-(trifluoromethyl)-2(1H)-quinolinone(328956-08-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 328956-08-7(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C10H5F4NO/c11-5-1-2-8-6(3-5)7(10(12,13)14)4-9(16)15-8/h1-4H,(H,15,16)

Upstream product

• 371-40-4 4-fluoroaniline 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 

Downstream Products

• 596845-42-0 6-fluoro-4-trifluoromethyl-2-quinolinecarboxylic acid 
• 596845-53-3 6-fluoro-4-trifluoromethyl-3-quinolinecarboxylic acid 
• 596845-30-6 2-bromo-6-fluoro-4-(trifluoromethyl)quinoline 

Relevant articles and documents

An Improved Access to 4-Trifluoromethyl-2(1H)-quinolinones: The "Watering Protocol"

Condensation of anilines with ethyl 4,4,4-trifluoroacetoacetate (7) to afford the corresponding 4,4,4-trifluoro-3-oxobutaneanilides (10), precursors to 4-(trifluoromethyl)-2-quinolinones (11), can be favored and the competing condensation to produce the e

Bicyclic androgen and progesterone receptor modulator compounds and methods

The present invention is directed to compounds, pharmaceutical compositions, and methods for modulating processes mediated by AR and PR. More particularly, the invention relates to nonsteroidal compounds and compositions that are high affinity, high specificity agonists, partial agonists (i.e., partial activators and/or tissue-specific activators) and antagonists for AR and PR. Also provided are methods of making such compounds and pharmaceutical compositions, as well as critical intermediates used in their synthesis.

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.