483-69-2

Usage

Uses

Used in Pharmaceutical Industry:
5-trifluoroMethyl-8-quinolinaMine is utilized as a building block in organic synthesis for the development of new drugs and agrochemicals. Its incorporation into molecules can enhance biological activity and metabolic stability, making it a valuable tool in drug discovery and design.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5-trifluoroMethyl-8-quinolinaMine is employed for its potential biological properties and versatile applications. Its unique structure allows for the creation of compounds with improved pharmacological profiles, contributing to advancements in therapeutic agents.

Upstream product

• 316-76-7 8-nitro-5-trifluoromethyl-quinoline 
• 402-14-2 2-nitro-5-(trifluoromethyl)aniline 
• 578-66-5 8-amino quinoline 
• 2314-97-8 iodotrifluoromethane 
• 1961266-44-3 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate 
• 33757-48-1 N-quinolin-8-yl-benzamide 
• 454-79-5 2-Bromo-5-trifluoromethylaniline 
• 917251-92-4 8-bromo-5-(trifluoromethyl)quinoline 
• 170891-76-6 α,α,α-trimethyl-N-(quinolin-8-yl)acetamide 
• 887144-94-7 Togni's reagent II 

Downstream Products

• 342-30-3 5-(trifluoromethyl)quinolone 
• 316-99-4 N-(5-(trifluoromethyl)quinolin-8-yl)acetamide 

Relevant academic research and scientific papers

Systematic ligand variation to modulate the electrochemical properties of iron and manganese complexes

A series of iron(+iii) and manganese(+ii) complexes based on the dpaqR-ligand system (dpaq = 2-[bis(pyridine-2-ylmethyl)]amino-N-quinolin-8-yl-acetamide) were investigated using cyclic voltammetry (CV) to elucidate how the electronic properties of the ligands influence the overpotential and catalytic current in the context of water oxidation catalysis. For the Fe-complexes an electron withdrawing NO2 or CF3 group attached to the 5-position of the quinoline unit increased the catalytic current, but only with a simultaneous increase of the overpotential. However, when a pyrene moiety was attached to the dipicolylamine unit of the ligand, the overpotential decreased with concomitant increase of the catalytic current. Although the manganese complexes showed no reversible formation of a molecular catalytically active species for water oxidation, the variations of the ligand scaffold affected largely the same trends in their electrochemical behavior.

Simple Photo-Induced Trifluoromethylation of Aromatic Rings

The trifluoromethylation of various aromatic compounds with Umemoto reagent II (2,8-difluoro-5-(trifluoromethyl)-5 H -dibenzo[ b, d ]thiophen-5-ium triflate) proceeded in moderate to good yields under simple photo-irradiation conditions without any cataly

Auxiliary-Directed C(sp3)?H Arylation by Synergistic Photoredox and Palladium Catalysis

Herein we describe the auxiliary-directed arylation of unactivated C(sp3)?H bonds with aryldiazonium salts, which proceeds under synergistic photoredox and palladium catalysis. The site-selective arylation of aliphatic amides with α-quaternary centres is achieved with high selectivity for β-methyl C(sp3)?H bonds. This operationally simple method is compatible with carbocyclic amides, a range of aryldiazonium salts and proceeds at ambient conditions.

5-Position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives

We developed a copper-catalyzed 5-position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives. The reaction proceeded with high functional group tolerance under mild conditions. In the case of quinolines with an amide, carbamate, urea, or sulfonamide group at the 8-position of quinoline moieties, a radical scavenger experiment indicated that the reaction proceeded via a radical pathway. The protecting group of an 8-amidoquinoline derivative could be removed by hydrolysis. On the other hand, the trifluoromethylation of 8-aminoquinolines was also promoted by other Lewis acids as well as a copper catalyst and proceeded even in the presence of a radical scavenger. These results indicated that the trifluoromethylation of 8-aminoquinolines proceeded via a Friedel-Crafts-type reaction. Interestingly, the copper salt works as either a catalyst for the formation of a CF3 radical or a Lewis acid to promote a Friedel-Crafts-type reaction, depending on the substrate.

Heterogeneous Chitosan@Copper(II)-Catalyzed Remote Trifluoromethylation of Aminoquinolines with the Langlois Reagent by Radical Cross-Coupling

The first remote C?H trifluoromethylation of N-(quinolin-8-yl)benzamide derivatives was accomplished with a user-friendly chitosan-based heterogeneous copper catalyst under mild conditions. The position-selective C?H activation protocol afforded the corresponding coupling products in good to excellent yields with excellent reusability of the catalyst by using the low-costing and stable Langlois reagent (CF3SO2Na) as the “CF3” source. Furthermore, control experiments suggested a single-electron-transfer process played a vital role in the heterogeneous C?CF3 cross-coupling.

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.

Trifluoromethylation of various aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide

Trifluoromethylation of aromatic and hetero-aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide was investigated. Various trifluoromethylated benzene derivatives, six-membered nitrogen-containing aromatic compounds and five-membered hetero-aromatic compounds were obtained under mild conditions. General orientation of electrophilic substitution of aromatic compounds was observed similarly as reported in other radical trifluoromethylation previously.

Experimental and Computational Studies of Trifluoromethylation of Aromatic Amines by the System Trifluoroiodomethane-Zinc-Sulfur Dioxide

Several trifluoromethyl-substituted aromatic and heteroaromatic amines have been obtained by the reactions of the corresponding amines with the title reagent system.Computational results provide rationalization for the observed regioselectivities and support a mechanism in which the electrophilic trifluoromethyl radicals interact with the aromatic ring at the sites with the greatest electron density of the HOMO orbitals, and then the resultant adducts are oxidized to cations.The products obtained are potential building blocks for a number of heterocyclic systems.