317-57-7

Basic information

• Product Name: 8-Trifluoromethylquinoline
• Synonyms: 8-(Trifluoromethyl)quinoline;8-Trifluoromethylquinoline;8-trifluoromethylQUINOLINE:8-(trifluoromethyl)QUINOLINE
• CAS NO: 317-57-7
• Molecular Formula: C10H6F3N
• Molecular Weight: 197.16
• EINECS: 197.2
• Mol File: 317-57-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 66 °C
• Boiling Point: 244 °C
• Flash Point: 101 °C
• Appearance: /Solid
• Density: 1.311
• Vapor Pressure: 0.049mmHg at 25°C
• Refractive Index: 1.54
• PKA: 2.72±0.17(Predicted)
• CAS DataBase Reference: 8-Trifluoromethylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Trifluoromethylquinoline(317-57-7)
• EPA Substance Registry System: 8-Trifluoromethylquinoline(317-57-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 317-57-7(Hazardous Substances Data)

Usage

General Description

8-Trifluoromethylquinoline is a chemical compound that belongs to the quinoline family and contains a trifluoromethyl group. It is primarily used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and fluorescent dyes. The trifluoromethyl group in the molecule makes it a versatile reagent for introducing fluorine atoms into organic compounds, which can enhance their biological activity or chemical properties. 8-Trifluoromethylquinoline has been studied for its potential applications in the development of new drugs and materials due to its unique chemical structure and properties. Additionally, 8-Trifluoromethylquinoline has shown promise as a fluorescent probe in bioimaging and diagnostic applications due to its ability to emit light in response to specific biological targets. Overall, 8-Trifluoromethylquinoline is a valuable chemical with diverse potential applications across various industries.

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

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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.

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.