1644-14-0

Basic information

• Product Name: 6-Fluoroquinoxaline
• Synonyms: Quinoxaline, 6-fluoro-
• CAS NO: 1644-14-0
• Molecular Formula: C₈H₅FN₂
• Molecular Weight: 148.14
• Mol File: 1644-14-0.mol

Chemical Properties

• Melting Point: 33-35 °C
• Boiling Point: 241.9°C at 760 mmHg
• Flash Point: 100.1°C
• Appearance: /
• Density: 1.297g/cm³
• Vapor Pressure: 0.0543mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.11±0.30(Predicted)
• CAS DataBase Reference: 6-Fluoroquinoxaline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Fluoroquinoxaline(1644-14-0)
• EPA Substance Registry System: 6-Fluoroquinoxaline(1644-14-0)

Safety Data

• Hazardous Substances Data: 1644-14-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Fluoroquinoxaline is utilized as a key intermediate in the synthesis of various pharmaceutical compounds for its potential to enhance the pharmacological properties of the final products. The incorporation of a fluorine atom can significantly alter the lipophilicity, metabolic stability, and receptor binding affinity of the resulting molecules, thereby improving their therapeutic efficacy.
Used in Antimicrobial Applications:
6-Fluoroquinoxaline is employed as an antimicrobial agent, leveraging its ability to inhibit the growth of various microorganisms. Its unique structure allows it to target specific cellular processes in bacteria and other pathogens, making it a promising candidate for the development of new antimicrobial drugs to combat drug-resistant infections.
Used in Antiviral Applications:
6-Fluoroquinoxaline is also being studied for its potential as an antiviral agent, with the capacity to interfere with viral replication and assembly processes. Its unique chemical properties enable it to target specific viral enzymes or receptors, offering a new approach to treating viral infections and mitigating the emergence of drug-resistant strains.
Used in Drug Discovery and Development:
6-Fluoroquinoxaline serves as a valuable tool in drug discovery and development, providing researchers with a versatile compound that can be modified and optimized to create new therapeutic agents. Its unique structural features and potential pharmacological properties make it an attractive starting point for the design of novel drugs targeting a wide range of medical conditions.

InChI:InChI=1/C8H5FN2/c9-6-1-2-7-8(5-6)11-4-3-10-7/h1-5H

Upstream product

• 131543-46-9 Glyoxal 
• 367-31-7 4-fluoro-1,2-phenylenediamine 
• 50998-17-9 6-bromoquinoxaline 
• 364-78-3 2-nitro-4-fluoroaniline 
• 852432-98-5 (quinoxalin-6-yl)boronic acid 

Relevant articles and documents

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.

Aqueous hydrofluoric acid catalyzed facile synthesis of 2,3,6-substituted quinoxalines

A versatile synthetic route for the preparation of 2,3,6-trisubstituted quinoxalines in excellent yield is developed from θ-diamines and 1,2-dicarbonyl compounds in which aqueous hydrofluoric acid was employed as the medium and catalyst. Other salient features of this protocol include milder conditions, absence of coupling agents, and easy workup procedures.

Pd-catalyzed nucleophilic fluorination of aryl bromides

On the basis of mechanism-driven reaction design, a Pd-catalyzed nucleophilic fluorination of aryl bromides and iodides has been developed. The method exhibits a broad substrate scope, especially with respect to nitrogen-containing heteroaryl bromides, and proceeds with minimal formation of the corresponding reduction products. A facilitated ligand modification process was shown to be critical to the success of the reaction.

FLUORINATION OF ORGANIC COMPOUNDS

Methods for fluorinating organic compounds are described herein.

Fluorination of boronic acids mediated by silver(I) Triflate

A regiospecific Ag-mediated fluorination reaction of aryl- and alkenylboronic acids and esters Is reported. The fluorination reaction uses commercially available reagents, does not require the addition of exogenous ligands, and can be performed on a multigram scale. This report discloses the first practical reaction sequence from arylboronic acid to aryl fluorides.

Preparation of 6-substituted quinoxaline JSP-1 inhibitors by microwave accelerated nucleophilic substitution

A small library of 6-aminoquinoxalines has been prepared by nucleophilic substitution of 6-fluoroquinoxaline with amines and nitrogen-containing heterocycles under computer-controlled microwave irradiation. Some compounds were found to be potent inhibitors of JNK Stimulatory Phosphatase-1 (JSP-1) in an in vitro biological assay.