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
• Article Data: 12

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

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

Downstream Products

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

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.

SUBSTITUTED AZOLE DIONE COMPOUNDS WITH ANTIVIRAL ACTIVITY

Provided herein are methods of using substituted azole dione compounds for treatment of viral infections.

Novel Sulfonaminoquinoline Hepcidin Antagonists

The present invention relates to novel hepcidin antagonists, pharmaceutical compositions comprising them and the use thereof as medicaments for the use in the treatment of iron metabolism disorders, such as, in particular, iron deficiency diseases and anemias, in particular anemias in connection with chronic inflammatory diseases.

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