25199-77-3

Basic information

• Product Name: 4-(TRIFLUOROMETHYL)QUINOLINE
• Synonyms: 4-(TRIFLUOROMETHYL)QUINOLINE
• CAS NO: 25199-77-3
• Molecular Formula: C10H6F3N
• Molecular Weight: 197.16
• Mol File: 25199-77-3.mol

Chemical Properties

• Boiling Point: 135-137 °C(Press: 23 Torr)
• Appearance: /
• Density: 1.364 g/cm3
• PKA: 2.56±0.13(Predicted)
• CAS DataBase Reference: 4-(TRIFLUOROMETHYL)QUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(TRIFLUOROMETHYL)QUINOLINE(25199-77-3)
• EPA Substance Registry System: 4-(TRIFLUOROMETHYL)QUINOLINE(25199-77-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 25199-77-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(TRIFLUOROMETHYL)QUINOLINE is used as a building block for the synthesis of pharmaceuticals due to its unique properties and reactivity, contributing to the development of new drugs with diverse pharmacological activities.
Used in Agrochemical Industry:
Similarly, in the agrochemical sector, 4-(TRIFLUOROMETHYL)QUINOLINE serves as a key intermediate in the creation of agrochemicals, leveraging its structural features to enhance the effectiveness of these compounds in agricultural applications.
Used in Medicinal Chemistry:
4-(TRIFLUOROMETHYL)QUINOLINE is utilized as a scaffold in medicinal chemistry for the design and synthesis of bioactive molecules. Its presence in these molecules can potentially influence their pharmacological profiles, making it an important component in drug discovery and development processes.

Upstream product

• 134219-71-9 1-trifluoromethyl-3-(phenylamino)prop-2-en-1-one 
• 155495-61-7 2,2,2-Trifluoro-1-(4-trifluoromethyl-quinolin-3-yl)-ethanone 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 3964-04-3 4-bromoquinoline 
• 1895006-01-5 dimesityl(trifluoromethyl)sulfonium trifluoromethanesulfonate 
• 91-22-5 quinoline 
• 2806-29-3 2-chloro-4-(trifluoromethyl)quinoline 
• 62-53-3 aniline 
• 142503-36-4 1,1,1,5,5,5-Hexafluoro-3-phenylaminomethylene-pentane-2,4-dione 
• 25199-84-2 4-(trifluoromethyl)quinolin-2(1H)-one 
• 590372-17-1 2-bromo-4-(trifluoromethyl)quinoline 

Downstream Products

• 155495-82-2 4-trifluoromethyl-3-quinolinecarboxylic acid 

Relevant articles and documents

Metallaphotoredox Perfluoroalkylation of Organobromides

Ruppert-Prakash type reagents (TMSCF3, TMSC2F5, and TMSC3F7) are readily available, air-stable, and easy-to-handle fluoroalkyl sources. Herein, we describe a mild, copper-catalyzed cross-coupling of these fluoroalkyl nucleophiles with aryl and alkyl bromides to produce a diverse array of trifluoromethyl, pentafluoroethyl, and heptafluoropropyl adducts. This light-mediated transformation proceeds via a silyl-radical-mediated halogen atom abstraction pathway, which enables perfluoroalkylation of a broad range of organobromides of variable steric and electronic demand. The utility of the method is demonstrated through the late-stage functionalization of several drug analogues.

A radical approach to the copper oxidative addition problem: Trifluoromethylation of bromoarenes

Transition metal–catalyzed arene functionalization has been widely used for molecular synthesis over the past century. In this arena, copper catalysis has long been considered a privileged platform due to the propensity of high-valent copper to undergo reductive elimination with a wide variety of coupling fragments. However, the sluggish nature of oxidative addition has limited copper’s capacity to broadly facilitate haloarene coupling protocols. Here, we demonstrate that this copper oxidative addition problem can be overcome with an aryl radical–capture mechanism, wherein the aryl radical is generated through a silyl radical halogen abstraction. This strategy was applied to a general trifluoromethylation of aryl bromides through dual copper-photoredox catalysis. Mechanistic studies support the formation of an open-shell aryl species.

Borazine-CF3? Adducts for Rapid, Room Temperature, and Broad Scope Trifluoromethylation

A fluoroform-derived borazine CF3? transfer reagent is used to effect rapid nucleophilic reactions in the absence of additives, within minutes at 25 °C. Inorganic electrophiles spanning seven groups of the periodic table can be trifluoromethylated in high yield, including transition metals used for catalytic trifluoromethylation. Organic electrophiles included (hetero)arenes, enabling C?H and C?X trifluoromethylation reactions. Mechanistic analysis supports a dissociative mechanism for CF3? transfer, and cation modification afforded a reagent with enhanced stability.

4-Position-Selective C-H Perfluoroalkylation and Perfluoroarylation of Six-Membered Heteroaromatic Compounds

The first 4-position-selective C-H perfluoroalkylation and perfluoroarylation of six-membered heteroaromatic compounds were achieved using nucleophilic perfluoroalkylation and perfluoroarylation reagents. The regioselectivity was controlled by electrophilically activating the heteroaromatic rings, while sterically hindering the 2-position, with a sterically bulky borane Lewis acid. The reaction proceeded in good yield, even in gram scale, and by a sequential reaction without isolating the intermediates. This reaction could be applied to late-stage trifluoromethylation of a bioactive compound.

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.

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.

Synthesis of some fluorinated nitrogen heterocycles from (diethylaminomethylene) hexafluoroacetylacetone (DAMFA)

Simple and highly efficient syntheses of the title compounds from DAMFA are described in the quinoline, azepinonaphtalene, azaphenanthrene(s), pyridopyridine, pyrazole, pyrrole and pyrimidine series.

Regioselective synthesis of trifluoromethyl substituted quinolines from trifluoroacetyl acetylenes

Trifluoromethyl substituted quinolines have been prepared by 1,2- or 1,4-addition of anilines to trifluoroacetyl acetylenes followed by intramolecular acid catalyzed ring closure.