394-70-7

Usage

Uses

Used in Pharmaceutical Industry:
4-FLUOROQUINOLINE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds, particularly those belonging to the fluoroquinolone class of antibiotics. Its unique structure and properties make it a valuable building block in the development of new drugs with improved efficacy and reduced side effects.
Used in Research and Development:
In the field of research and development, 4-FLUOROQUINOLINE serves as a key compound for studying the effects of fluorination on the biological activity of quinilone derivatives. This helps researchers understand the structure-activity relationship and design more effective and safer drugs.
Used in Mutagenesis Studies:
4-FLUOROQUINOLINE is used as a mutagenic agent in Salmonella typhimurium TA100 for evaluating its potential mutagenic effects in the presence of microsomal activation. This information is crucial for assessing the safety and potential risks associated with the compound's use in various applications.
Used in Toxicology and Safety Assessment:
4-FLUOROQUINOLINE is also used in toxicology and safety assessment studies to determine its effects on unscheduled DNA synthesis (UDS) in rat hepatocytes. This helps in understanding the potential genotoxicity and overall safety profile of 4-FLUOROQUINOLINE, which is essential for its application in the pharmaceutical industry and other related fields.

InChI:InChI=1/C9H6FN/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H

Upstream product

• 578-68-7 4-aminoquinoline 
• 75-07-0 acetaldehyde 
• 88-17-5 2-(trifluoromethyl)benzenamine 
• 208934-37-6 quinolin-4-yl trifluoromethanesulfonate 
• 611-35-8 4-chloroquinoline 
• 3964-04-3 4-bromoquinoline 

Downstream Products

• 396-30-5 6-fluoroquinoline 
• 442-65-9 4-fluoro-benzenesulfonic acid-(6-fluoro-[8]quinolylamide) 
• 343-26-0 6-fluoro-8-nitroquinoline 
• 343-54-4 8-amino-6-fluoroquinoline 

Relevant academic research and scientific papers

Tetramethylammonium Fluoride Alcohol Adducts for SNAr Fluorination

Nucleophilic aromatic fluorination (SNAr) is among the most common methods for the formation of C(sp2)-F bonds. Despite many recent advances, a long-standing limitation of these transformations is the requirement for rigorously dry, aprotic conditions to maintain the nucleophilicity of fluoride and suppress the generation of side products. This report addresses this challenge by leveraging tetramethylammonium fluoride alcohol adducts (Me4NF·ROH) as fluoride sources for SNAr fluorination. Through systematic tuning of the alcohol substituent (R), tetramethylammonium fluoride tert-amyl alcohol (Me4NF·t-AmylOH) was identified as an inexpensive, practical, and bench-stable reagent for SNAr fluorination under mild and convenient conditions (80 °C in DMSO, without the requirement for drying of reagents or solvent). A substrate scope of more than 50 (hetero) aryl halides and nitroarene electrophiles is demonstrated.

Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands

Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.

Metal-Catalyzed Carbon-Fluorine Bond Formation

One aspect of the invention relates to a metal-catalyzed conversion of aryl halides and sulfonates to the corresponding aryl fluorides. Another aspect of the invention relates to a metal-catalyzed conversion of heteroaryl halides and sulfonates to the corresponding heteroaryl fluorides. Another aspect of the invention relates to a metal-catalyzed conversion of vinyl halides and sulfonates to the corresponding vinyl fluorides. In certain embodiments, simple fluoride sources, such as AgF and CsF, are used. In certain embodiments, the transformations tolerate a wide range of functional groups, allowing for introduction of fluorine atoms into highly functionalized organic molecules.

Accelerating palladium-catalyzed C-F bond formation: Use of a microflow packed-bed reactor

A flow process for Pd-catalyzed C-F bond formation is described. A microreactor with a packed-bed design allows for easy handling of large quantities of insoluble CsF with precise control over reaction times, efficient mixing, and the ability to safely handle elevated temperatures and pressures. A variety of aryl triflates, including heteroaryl ones, were converted into aryl fluorides in short reaction times (see scheme).

The o-Amino-Trifluoromethyl Functionality as a Novel Synthon for 4-Fluoroquinolines

2-Substituted 4-fluoroquinolines 3 are obtained by the reaction of 2-(trifluoromethyl)aniline (1) with lithium enolates 2 derived from methyl ketones.A similar reaction of 1 with lithium enolate of acetaldehyde produces 4-fluoroquinoline. 1-Fluoro-3-phenyl-4,6-phenanthroline (18) is obtained by treatment of lithium enolate of acetophenone with 4-(trifluoromethyl)quinolin-3-amine (17).By contrast, (Z)-N-carboxamides 10 and 12 are the products of the reaction of 1 with the respective enolate ions derived from 3-pentanone and isobutyl phenyl ketone.A unified mechanism for the formation of quinolines and carboxamides is proposed.