580-21-2

Basic information

• Product Name: 2-FLUOROQUINOLINE
• Synonyms: 2-FLUOROQUINOLINE
• CAS NO: 580-21-2
• Molecular Formula: C₉H₆FN
• Molecular Weight: 147.1490432
• Mol File: 580-21-2.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 241.9 °C at 760 mmHg
• Flash Point: 100.1 °C
• Appearance: /
• Density: 1.216 g/cm³
• Vapor Pressure: 0.0544mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: Room temperature.
• PKA: -0.68±0.40(Predicted)
• CAS DataBase Reference: 2-FLUOROQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-FLUOROQUINOLINE(580-21-2)
• EPA Substance Registry System: 2-FLUOROQUINOLINE(580-21-2)

Safety Data

• Hazardous Substances Data: 580-21-2(Hazardous Substances Data)

Usage

General Description

2-Fluoroquinoline is a chemical compound belonging to the class of quinoline derivatives, which are heterocyclic aromatic compounds containing a benzene ring fused to a pyridine ring. It is characterized by the presence of a fluorine atom at the 2-position of the quinoline ring. 2-Fluoroquinoline has found applications in the pharmaceutical and agrochemical industries as a building block for the synthesis of various bioactive molecules, including pharmaceutical drugs and agrochemicals. It is also used as a precursor in the production of fluorescent dyes and as a reagent in organic synthesis. Additionally, 2-Fluoroquinoline has been studied for its potential biological activities, including antibacterial, antifungal, and anti-inflammatory properties, making it a subject of interest in medicinal chemistry and drug discovery.

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

Upstream product

• 580-22-3 2-aminoquinoline 
• 612-62-4 2-Chloroquinoline 
• 91-22-5 quinoline 
• 67-56-1 methanol 
• 2005-43-8 2-bromoquinoline 
• 93-10-7 quinoline-2-carboxylic acid 

Downstream Products

• 59-31-4 2-quinolone 
• 7783-54-2 nitrogen trifluoride 
• 128676-86-8 (2-fluoro-3-quinolyl)phenylmethanol 
• 128676-87-9 (2-fluoro-3-quinolyl) phenyl ketone 
• 7596-64-7 6-Hydroxychinolinsaeure 
• 59-31-4 2-hydroxyquinoline 

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.

Nucleophilic Fluorination of Heteroaryl Chlorides and Aryl Triflates Enabled by Cooperative Catalysis

Aryl and heteroaryl fluorides are growing to be dominant motifs in pharmaceuticals and agrochemicals, yet they are rare in both nature and commodity chemicals. As a consequence, there is an increasingly urgent need to develop mild, cost-effective, and scalable methods for fluorination. The most straightforward route to synthesize aryl fluorides is through the halide exchange "halex"reaction, but conditions, cost, and atom economy preclude most available methods from large-scale manufacturing processes. We report a new approach that leverages the cooperative action of 18-crown-6 ether and tetramethylammonium chloride to catalytically access the reactivity of tetramethylammonium fluoride and achieve halex fluorinations under mild conditions with operational ease. The described methodology readily converts both heteroaryl chlorides and aryl triflates to their corresponding (hetero)aryl fluorides in high yields and purities.

PROCESS FOR FLUORINATING COMPOUNDS

Disclosed are mild temperature (e.g., from 0 to 80°C) SNAr fluorinations of a variety of halide and sulfonate substituted aryl and heteroaryl substrates using NMe4F.