394-70-7

Basic information

• Product Name: 4-FLUOROQUINOLINE
• Synonyms: 4-FLUOROQUINOLINE
• CAS NO: 394-70-7
• Molecular Formula: C9H6FN
• Molecular Weight: 147.1490432
• Product Categories: Aromatics;Heterocycles;Mutagenesis Research Chemicals
• Mol File: 394-70-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 180-195 °C
• Boiling Point: 238.4°Cat760mmHg
• Flash Point: 98°C
• Appearance: /
• Density: 1.216g/cm³
• Vapor Pressure: 0.0654mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 3.87±0.13(Predicted)
• CAS DataBase Reference: 4-FLUOROQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-FLUOROQUINOLINE(394-70-7)
• EPA Substance Registry System: 4-FLUOROQUINOLINE(394-70-7)

Safety Data

• Hazardous Substances Data: 394-70-7(Hazardous Substances Data)

Usage

Description

4-FLUOROQUINOLINE is a fluorinated quinilone compound that has been found to exhibit some mutagenic activity in the presence of microsomal activation in Salmonella typhimurium TA100. However, it has shown no significant effect on unscheduled DNA synthesis (UDS) in rat hepatocytes when compared to other fluoroquinones.

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 
• 3964-04-3 4-bromoquinoline 
• 208934-37-6 quinolin-4-yl trifluoromethanesulfonate 
• 611-35-8 4-chloroquinoline 

Downstream Products

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

Relevant articles and documents

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.

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.

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.