83842-55-1

Basic information

• Product Name: 2-Trifluoromethyl-1H-quinolin-4-one
• Synonyms: 2-Trifluoromethyl-1H-quinolin-4-one;2-(trifluoroMethyl)-1,4-dihydroquinolin-4-one;2-(trifluoromethyl)-4(1H)-Quinolinone
• CAS NO: 83842-55-1
• Molecular Formula: C10H6F3NO
• Molecular Weight: 213.1559496
• Mol File: 83842-55-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Trifluoromethyl-1H-quinolin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Trifluoromethyl-1H-quinolin-4-one(83842-55-1)
• EPA Substance Registry System: 2-Trifluoromethyl-1H-quinolin-4-one(83842-55-1)

Safety Data

• Hazardous Substances Data: 83842-55-1(Hazardous Substances Data)

Usage

General Description

2-Trifluoromethyl-1H-quinolin-4-one is a chemical compound belonging to the quinoline class. It is also known as CF3-quinolin-4-one or 2-trifluoromethylquinolin-4(1H)-one. 2-Trifluoromethyl-1H-quinolin-4-one has a molecular formula of C10H6F3NO and a molecular weight of 207.15 g/mol. It is a yellow solid with a melting point of 89-91°C. 2-Trifluoromethyl-1H-quinolin-4-one is used as a building block in the synthesis of pharmaceutical and agrochemical compounds. It has the potential to exhibit biological activity and may have applications in drug discovery and development.

Upstream product

• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 6141-26-0 2-Trifluoroacetylaminoacetophenone 
• 551-93-9 2-aminoacetophenone 
• 62-53-3 aniline 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 383-63-1 ethyl trifluoroacetate, 
• 535993-23-8 3,3-dihydroxy-1-(2-trifluoroacetamidophenyl)-4,4,4-trifluorobutan-1-one 

Downstream Products

• 587886-11-1 4-bromo-2-trifluoromethyl-3-quinolinecarboxylic acid 
• 587886-19-9 4-bromo-2-trifluoromethyl-3-quinolinecarboxylic acid methyl ester 
• 587886-26-8 2-trifluoromethyl-3-quinolinecarboxylic acid 
• 18706-39-3 2-(trifluoromethyl)quinoline-4-carboxylic acid 
• 18706-25-7 4-bromo-2-(trifluoromethyl)quinoline 

Relevant articles and documents

Quinoline and ferrocene conjugates: Synthesis, computational study and biological evaluations

Novel O-alkylated quinoline and N-alkylated 4-quinolone derivatives attached to the ferrocene moiety through 4,1- (7a–d, 8a–d and 12a–d) and 1,4-disubstituted (9a, 9b, 10a and 10b) 1,2,3-triazole moiety were synthesized. The observed regioselectivity of O- vs. N-alkylation was explored by the use of NMR and computational techniques. Among the N-alkylated derivatives, the quinolone-ferrocene conjugate 9a displayed marked activities against chronic myeloid leukemia in blast crisis (K562) and Burkitt lymphoma (Raji). The 6-chloroquinolone-ferrocene conjugate 12c, with selective inhibitory activity on Raji cells and no cytostatic effect on normal MDCK1 cells was highlighted as the most promising anticancer organometallic complex in a group of O-alkylated quinolines.

Mapping Dual-Base-Enabled Nickel-Catalyzed Aryl Amidations: Application in the Synthesis of 4-Quinolones

The C?N cross-coupling of (hetero)aryl (pseudo)halides with NH substrates employing nickel catalysts and organic amine bases represents an emergent strategy for the sustainable synthesis of (hetero)anilines. However, unlike protocols that rely on photoredox/electrochemical/reductant methods within NiI/III cycles, the reaction steps that comprise a putative Ni0/II C?N cross-coupling cycle for a thermally promoted catalyst system using organic amine base have not been elucidated. Here we disclose an efficient new nickel-catalyzed protocol for the C?N cross-coupling of amides and 2′-(pseudo)halide-substituted acetophenones, for the first time where the (pseudo)halide is chloride or sulfonate, which makes use of the commercial bisphosphine ligand PAd2-DalPhos (L4) in combination with an organic amine base/halide scavenger, leading to 4-quinolones. Room-temperature stoichiometric experiments involving isolated Ni0, I, and II species support a Ni0/II pathway, where the combined action of DBU/NaTFA allows for room-temperature amide cross-couplings.

New trifluoromethyl quinolone derivatives: Synthesis and investigation of antimicrobial properties

A series of quinolone derivatives, containing different heterocyclic amines were prepared. Synthesized compounds were evaluated for their in vitro antimicrobial activities against two Gram-positive bacteria, three Gram-negative bacteria as well as four fungi. All the derivatives showed good activity towards Gram-positive bacteria and less activity towards Gram-negative bacteria. They also showed moderate to comparable activity against Aspergillus niger and Candida albicans and low to moderate antifungal activity against Aspergillus fumigatus and Aspergillus flavus.