55687-23-5

Basic information

• Product Name: 6-Fluoroquinoxalin-2(1H)-one
• Synonyms: 6-Fluoroquinoxalin-2(1H)-one;6-fluoro-1,2-dihydroquinoxalin-2-one;6-fluoroquinoxalin-2-ol
• CAS NO: 55687-23-5
• Molecular Formula: C₈H₅FN₂O
• Molecular Weight: 164.14
• Mol File: 55687-23-5.mol

Chemical Properties

• Melting Point: 300-302 °C(Solv: tetrahydrofuran (109-99-9))
• Appearance: /
• Density: 1.442g/cm³
• Refractive Index: 1.642
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 7.92±0.70(Predicted)
• CAS DataBase Reference: 6-Fluoroquinoxalin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Fluoroquinoxalin-2(1H)-one(55687-23-5)
• EPA Substance Registry System: 6-Fluoroquinoxalin-2(1H)-one(55687-23-5)

Safety Data

• Hazardous Substances Data: 55687-23-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
6-Fluoroquinoxalin-2(1H)-one is utilized as a key intermediate in the synthesis of pharmaceuticals and medicinal compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications, including treatments for various diseases and conditions.
Used in Organic Synthesis:
In the field of organic synthesis, 6-Fluoroquinoxalin-2(1H)-one is employed as a versatile building block for the preparation of diverse organic compounds. Its reactivity and structural features enable the synthesis of a wide range of molecules with different properties, making it a valuable component in the development of new materials and chemical products.
Used in Research and Development:
6-Fluoroquinoxalin-2(1H)-one is also used in research and development settings to explore its potential uses and properties in various fields. Further studies and investigations may reveal its applications in areas such as drug discovery, material science, and other emerging technologies.

InChI:InChI=1/C8H5FN2O/c9-5-1-2-6-7(3-5)10-4-8(12)11-6/h1-4H,(H,11,12)

Upstream product

• 145323-37-1 N-(4-fluoro-2-nitrophenyl)sarcosine ethyl ester 
• 148010-65-5 6-fluoro-1,2,3,4-tetrahydroquinoxalin-2-one 
• 98416-74-1 6-Fluoro-4-oxy-1H-quinoxalin-2-one 
• 446-35-5 2,4-Difluoronitrobenzene 
• 55687-24-6 N-(5-fluoro-2-nitrophenyl)glycine ethyl ester 
• 96089-45-1 N-(4-Fluoro-2-nitro-phenyl)-3-oxo-butyramide 
• 924-44-7 glyoxylic acid ethyl ester 
• 367-31-7 4-fluoro-1,2-phenylenediamine 
• 364-78-3 2-nitro-4-fluoroaniline 

Downstream Products

• 55687-33-7 2-chloro-6-fluoro-quinoxaline 
• 934690-32-1 6-fluoro-7-nitroquinoxalin-2⁽¹⁾-one 
• 1233932-59-6 2-chloro-7-fluoroquinoxaline 

Relevant articles and documents

Electro-reductive C-H cyanoalkylation of quinoxalin-2(1H)-ones

Herein, we report a practical electro-reductive protocol for the direct C–H cyanoalkylation of quinoxalin-2(1H)-ones via iminyl radical-mediated ring opening. These mild reactions proceed under metal-, reductant-, and reagent-free conditions to provide synthetically useful cyanoalkylated quinoxalin-2(1H)-ones.

Electro-oxidative C-H alkylation of quinoxalin-2(1: H)-ones with organoboron compounds

Radical cleavage of C-B bonds to accomplish C-H functionalization is synthetically appealing but practically challenging. We report herein a mild electro-oxidative method for efficient C-H alkylation of quinoxalin-2(1H)-ones by means of radical addition reactions of alkyl boronic acids and esters and alkyl trifluoroborates to afford C-C coupled products. This journal is

Electro-oxidative C-H azolation of quinoxalin-2(1H)-ones

We have developed a practical, general protocol for direct C-H azolation reactions of quinoxalin-2(1H)-ones by electro-oxidative cross-coupling. These mild reactions proceed under metal-, oxidant-, and reagent-free conditions to provide synthetically useful azolated quinoxalin-2(1H)-ones. Furthermore, the reactions can be carried out with a pencil lead as an electrode and a 3 V battery as a power source, revealing the remarkable flexibility of this protocol.

N, N, N', N'-Tetramethylethylenediamine-Enabled Photoredox-Catalyzed C-H Methylation of N-Heteroarenes

Aiming at the valuable methylation process, readily available and inexpensive N,N,N′,N′-tetramethylethylenediamine (TMEDA) was first identified as a new methyl source in photoredox-catalyzed transformation in this work. By virtue of this simple methylating reagent, a facile and practical protocol for the direct C-H methylation of N-heteroarenes was developed, featuring mild reaction conditions, broad substrate scope, and scalability. Mechanistic studies disclosed that a sequential photoredox, base-assisted proton shift, fragmentation, and tautomerization process was essentially involved.

Visible Light-Promoted Radical Relay Cyclization/C-C Bond Formation of N-Allylbromodifluoroacetamides with Quinoxalin-2(1 H)-ones

A visible light-promoted radical relay of N-allylbromodifluoroacetamide with quinoxalin-2(1H)-ones was developed in which 5-exo-trig cyclization and C-C bond formation were involved. This protocol was performed under mild conditions to facilely offer a variety of hybrid molecules bearing both quinoxalin-2(1H)-one and 3,3-difluoro-γ-lactam motifs. These prepared novel skeletons would expand the accessible chemical space for structurally complex heterocycles with potential biological activities.

Palladium-catalyzed direct Hiyama arylation of quinoxalin-2(1H)-ones with aryl siloxanes in water

An efficient method for palladium-catalyzed direct Hiyama coupling of various quinoxalin-2(1H)-ones with aryl siloxanes has been developed. The protocol provides a convenient access to a variety of useful C3-arylated 1-methylquinoxalin-2(1H)-one derivatives in reasonable yields by using low cost water as a solvent and oxygen as an oxidant.

Electrochemically C-H/S-H Oxidative Cross-Coupling between Quinoxalin-2(1 H)-ones and Thiols for the Synthesis of 3-Thioquinoxalinones

An electrochemical method for the C(sp2)-H thioetherification of quinoxalin-2(1H)-ones with primary, secondary, and tertiary thiols has been reported. Various quinoxalin-2(1H)-ones underwent this thioetherification smoothly under metal- A nd chemical oxidant-free conditions, affording 3-alkylthiol-substituted quinoxalin-2(1H)-ones in moderate to good yields.

Electrochemical decarboxylative C3 alkylation of quinoxalin-2(1: H)-ones with N -hydroxyphthalimide esters

We have developed a protocol for electrochemical decarboxylative C3 alkylation of a wide range of quinoxalin-2(1H)-ones under metal- and additive-free conditions. N-Hydroxyphthalimide esters derived from chain, cyclic, primary, secondary, and tertiary carboxylic acids with a broad scope proved to be suitable substrates. This operationally simple protocol performed in an undivided cell under constant-current conditions is suitable for late-stage functionalization of quinoxalin-2(1H)-ones. The reactions can even be carried out with a 3 V battery as a power source, which demonstrates that organic electrosynthesis can be accomplished without the need for specialized equipment.

Construction of C(sp2)?C(sp3) Bond between Quinoxalin-2(1H)-ones and N-Hydroxyphthalimide Esters via Photocatalytic Decarboxylative Coupling

A novel visible-light-driven decarboxylative coupling of alkyl N-hydroxyphthalimide esters (NHP esters) with quinoxalin-2(1H)-ones has been developed. This C(sp2)?C(sp3) bond-forming transformation exhibits excellent substrate generality with respect to both the coupling partners. Of note, a series of 3-primary alkyl-substituted quinoxalin-2(1H)-ones that were difficult to synthesize by previous methods could be obtained in moderate to excellent yields. Additionally, the mild conditions, easy availability of substrates, wide functional group tolerance and operational simplicity make this protocol practical in the synthesis of 3-alkylated quinoxalin-2(1H)-ones.

Electrochemically dehydrogenative C-H/P-H cross-coupling: Effective synthesis of phosphonated quinoxalin-2(1: H)-ones and xanthenes

An efficient electrochemical approach for the C(sp2)-H phosphonation of quinoxalin-2(1H)-ones and C(sp3)-H phosphonation of xanthenes has been developed. The chemistry was performed in an undivided cell under constant current conditions and features a wide range of substrates, up to 99% yield and it is free of transition-metal catalysts- A nd external oxidants, thereby providing a straightforward approach for dehydrogenative C-H/P-H cross-coupling. In addition, control experiments disclose that some of the reactions may involve a radical pathway.