25199-84-2

Basic information

• Product Name: 2-HYDROXY-4-(TRIFLUOROMETHYL)QUINOLINE
• Synonyms: BUTTPARK 33\04-80;2-HYDROXY-4-(TRIFLUOROMETHYL)QUINOLINE;4-(Trifluoromethyl)quinolin-2-ol;4-Trifluoromethyl-1H-quinolin-2-one;2-Hydroxy-4-(trifluoromethyl)quinoline ,98%;4-(trifluoromethyl)quinolin-2(1H)-one;2-hydroxy-4-(trifluoroMethyl)quinqline;4--(TrifluoroMethyl)quinoline-2(H)-one
• CAS NO: 25199-84-2
• Molecular Formula: C10H6F3NO
• Molecular Weight: 213.16
• Mol File: 25199-84-2.mol

Chemical Properties

• Melting Point: >240°C
• Boiling Point: 284 ºC
• Flash Point: 126 ºC
• Appearance: White/Solid
• Density: 1.391
• Vapor Pressure: 0.00304mmHg at 25°C
• Refractive Index: 1.516
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-HYDROXY-4-(TRIFLUOROMETHYL)QUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXY-4-(TRIFLUOROMETHYL)QUINOLINE(25199-84-2)
• EPA Substance Registry System: 2-HYDROXY-4-(TRIFLUOROMETHYL)QUINOLINE(25199-84-2)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 25199-84-2(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Synthesis

4-Trifluoromethylquinolin-2(1H)-one was prepared by reacting aniline and ethyl-4,4,4-trifluoroacetoacetate stirred in toluene.Experimental Procedure: In a 1 L round flask fitted with a reflux condenser a mixture of 25.60 g aniline, 50.0 g ethyl-4,4,4-trifluoroacetoacetate 300 ml toluene was heated to reflux in an oil bath at 130 °C. After 20 min 3 ml water was added and the mixture was heated at reflux for another 24 h. the reaction mixture was cooled to room temperature and concentrated under reduced pressure. A round flask with 200 mL H2SO4 was heated to 80°C and the crude oil from the step before was added in portions to the H2SO4 keeping the internal temperature below 90°C, total addition time was approximately 40 min. After addition was complete, the mixture was stirred at 80°C for 1 h, cooled and poured onto 400 g crushed ice. The resulting solids were filtered, washed with water, and dried under vacuum at 40°C to give 33.0 g (50%) product (4-Trifluoromethylquinolin-2(1H)-one) as a colorless solid.

InChI:InChI=1/C10H6F3NO/c11-10(12,13)7-5-9(15)14-8-4-2-1-3-6(7)8/h1-5H,(H,14,15)

Upstream product

• 62-53-3 aniline 
• 836-31-7 4,4,4-trifluoro-3-oxo-N-phenylbutyramide 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 404597-04-2 (Z)-3,4,4,4-Tetrafluoro-but-2-enoic acid phenylamide 

Downstream Products

• 2806-29-3 2-chloro-4-(trifluoromethyl)quinoline 
• 590372-17-1 2-bromo-4-(trifluoromethyl)quinoline 
• 328956-38-3 6-nitro-4-trifluoromethylquinolin-2(1H)-one 
• 328955-57-3 6-amino-4-(trifluoromethyl)quinoline-2-(1H)-one 
• 25199-77-3 4-(trifluoromethyl)quinoline 
• 155495-82-2 4-trifluoromethyl-3-quinolinecarboxylic acid 
• 590372-20-6 2-bromo-4-trifluoromethyl-3-quinolinecarboxylic acid 
• 1076236-51-5 C₁₀H₈F₃N₃ 
• 25199-89-7 4-trifluoromethyl-quinoline-2-carbonitrile 

Relevant articles and documents

Chemoselectivity in the reactions between ethyl 4,4,4-trifluoro-3-oxobutanoate and anilines: Improved synthesis of 2-trifluoromethyl-4- and 4-trifluoromethyl-2-quinolinones

Chemoselectivity in the reactions between ethyl 4,4, 4-trifluoroacetoacetate (ethyl 4,4,4-trifluoro-3-oxobutanoate) and various anilines was systematically studied as a function of the reaction conditions used (solvent/temperature, catalyst). The results obtained allowed chemoselective (>90%) synthesis of the corresponding ethyl 3-arylamino-4,4,4-trifluorobut-2-enoates and N-aryl-4,4,4-trifluoro-3-oxobutyramides, which were cyclized to afford 2-trifluoromethyl-4-quinolinones and 4-trifluoromethyl-2-quinolinones, respectively.

Discovery of 6-N,N-Bis(2,2,2-trifluoroethyl)amino-4- trifluoromethylquinolin-2(1H)-one as a novel selective androgen receptor modulator

The androgen receptor is a member of the extended family of nuclear receptors and is widely distributed throughout the body. Androgen therapy is used to compensate for low levels of the natural hormones testosterone (T) and dihydrotestosterone and consist

SUBSTITUTED AZOLE DIONE COMPOUNDS WITH ANTIVIRAL ACTIVITY

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The "off-shore" construction of optionally substituted 4-trifluoromethyl-2-quinolinones

Treatment of ortho-lithiated tert-butyl N-arylcarbamates (i.e., BOC-protected anilines) with N-(trifluoroacetyl)piperidine provides 2-(N-BOC-amino)aryl trifluoromethyl ketones which, upon consecutive reaction with an α-alkoxycarbonyl-substituted phosphoru

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

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.

Facile and regioselective synthesis of 4-fluoroalkyl-2-quinolinol

4-Fluoroalkyl-2-quinolinols were regioselectively synthesized in moderate to high yields by acid-assisted intramolecular ring-closure reaction of the corresponding N-aryl-3-oxa-polyfluoroalkanamides prepared from 2,2-dihydropolyfluoroalkanoic acids in two