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

Uses

A fluorinated quinilone that in the presence of microsomal activation exhibits some mutagenic activity in Salmonella typhimurium TA100 but showed no significant effect on unscheduled DNA synthesis (UDS) in rat hepatocytes compared to other fluoroquinones.

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

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 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.

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.