317-57-7

Usage

Uses

Used in Pharmaceutical Industry:
8-Trifluoromethylquinoline is used as a building block for the synthesis of various pharmaceuticals due to its ability to improve the biological activity of compounds by introducing fluorine atoms.
Used in Agrochemical Industry:
8-Trifluoromethylquinoline is used as a building block for the synthesis of agrochemicals, where its introduction of fluorine atoms can enhance the effectiveness of these compounds in agricultural applications.
Used in Fluorescent Dyes:
8-Trifluoromethylquinoline is used as a building block for the synthesis of fluorescent dyes, leveraging its unique chemical properties to create dyes with specific characteristics.
Used in Drug Development:
8-Trifluoromethylquinoline is used as a reagent in the development of new drugs, capitalizing on its potential to enhance the properties of drug candidates through the introduction of fluorine atoms.
Used in Bioimaging and Diagnostic Applications:
8-Trifluoromethylquinoline is used as a fluorescent probe for bioimaging and diagnostic applications, taking advantage of its ability to emit light in response to specific biological targets, which aids in visualizing and diagnosing various conditions.

InChI:InChI=1/C10H6F3N/c11-10(12,13)8-5-1-3-7-4-2-6-14-9(7)8/h1-6H

Upstream product

• 56-81-5 glycerol 
• 88-17-5 2-(trifluoromethyl)benzenamine 
• 1006-47-9 iodo-8 quinoleine 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 578-66-5 8-amino quinoline 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 887144-94-7 Togni's reagent II 
• 91-22-5 quinoline 
• 421-83-0 trifluoromethane sulfonyl chloride 

Downstream Products

• 75414-10-7 8-trifluoromethyl-5,6,7,8-tetrahydroquinoline 
• 75414-01-6 8-trifluoromethyl-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

The effect of photocatalyst excited state lifetime on the rate of photoredox catalysis

Four different iridium(iii) polypyridyl complexes with varying excited state lifetimes are used as photocatalysts to study the effect of excited state lifetime on the rate of a prototypical photoredox-catalyzed reaction, the trifluoromethylation of quinoline. An improved mechanistic understanding of the photocatalysis is achieved, enabling guided optimization of reaction conditions and elucidating the role of the photocatalyst excited state lifetime on the rate of photocatalysis.

Copper-catalyzed trifluoromethylation of organic zinc reagents with an electrophilic trifluoromethylating reagent

A copper-catalyzed trifluoromethylation of aryl, vinyl and alkyl zinc reagents with Togni's reagent was described. Mechanistic studies indicated that the aryl group is initially transferred from the zinc reagent to hypervalent iodine to form a tri-substituted hypervalent iodine intermediate. Consequent reductive-elimination via a concerted bond-forming step and/or radical pathway from this intermediate generates the trifluoromethylated arenes.

One-pot sandmeyer trifluoromethylation and trifluoromethylthiolation

Practical one-pot procedures were developed for both Sandmeyer-type trifluoromethylations and trifluoromethylthiolations. Starting from broadly available (hetero)aromatic amines, various benzotrifluorides were synthesized in high yields via in situ diazotization and copper-mediated trifluoromethylation using the inexpensive Ruppert-Prakash trifluoromethylating reagent. In the presence of sodium thiocyanate as a sulfur source, aryl trifluoromethyl thioethers are exclusively formed.

Sandmeyer trifluoromethylation of arenediazonium tetrafluoroborates

Copper capabilities: Diazonium salts are converted into the corresponding trifluoromethyl derivatives in the presence of a trifluoromethyl-copper complex generated in situ from CuSCN and the inexpensive, easy-to-use trifluoromethylating reagent Me3Si-CF3 (see scheme). This Sandmeyer-type reaction allows the straightforward synthesis of trifluoromethylated arenes and heteroarenes from the corresponding amines. Copyright

Copper-promoted sandmeyer trifluoromethylation reaction

A copper-promoted trifluoromethylation reaction of aromatic amines is described. This transformation proceeds smoothly under mild conditions and exhibits good tolerance of many synthetically relevant functional groups. It provides an alternative approach for the synthesis of trifluoromethylated arenes and heteroarenes. It also constitutes a new example of the Sandmeyer reaction.

A ligand-free copper-catalyzed decarboxylative trifluoromethylation of aryliodides with sodium trifluoroacetate using Ag2O as a promoter

A practical and ligand-free Cu-catalyzed decarboxylative trifluoromethylation of aryl iodides with sodium trifluoroacetate using Ag 2O as a promoter was reported. A variety of trifluoromethyl- substituted aromatics are synthesized in moderate to excellent yields and with wide functional-group tolerance under relatively mild reaction conditions. Georg Thieme Verlag Stuttgart · New York.