1196-57-2

Basic information

• Product Name: 2-Quinoxalinone
• Synonyms: 2-QUINOXALINOL;2-Quinoxalinone;2-HYDROXYQUINOXALINE;QUINOXALIN-2-OL;1,2-Dihydroquinoxalin-2-one;2-(1H)-Quinoxalinone;2(1H)-Quinoxalinone;2-Quinoxalone
• CAS NO: 1196-57-2
• Molecular Formula: C₈H₆N₂O
• Molecular Weight: 146.15
• EINECS: 214-815-6
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Quinoxalines
• Mol File: 1196-57-2.mol
• Article Data: 97

Chemical Properties

• Melting Point: 271-272°C
• Boiling Point: 265.75°C (rough estimate)
• Flash Point: 173.6 °C
• Appearance: /
• Density: 1.2312 (rough estimate)
• Vapor Pressure: 8.65E-06mmHg at 25°C
• Refractive Index: 1.4900 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Very Slightly, Heated)
• PKA: 9.20±0.50(Predicted)
• CAS DataBase Reference: 2-Quinoxalinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Quinoxalinone(1196-57-2)
• EPA Substance Registry System: 2-Quinoxalinone(1196-57-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/39-37/39
• WGK Germany: 3
• RTECS: VD3630000
• Hazardous Substances Data: 1196-57-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Quinoxalinone is used as a key intermediate in the synthesis of various organic compounds and pharmaceuticals. Its reactivity and structural features make it a valuable building block for the development of new molecules with potential applications in medicine and materials science.
Used in Material Science:
In the field of material science, 2-Quinoxalinone plays a crucial role in the epitaxial crystallization of syndiotactic polypropylene on 2-quinoxalinol, yielding the isochiral form II of syndiotactic polypropylene. This process contributes to the development of advanced polymer materials with improved properties and performance.
Used in Environmental Applications:
2-Quinoxalinone is known for its photocatalytic properties, which enable it to destroy antioxidant vitamins and biogenic amines in vitro. This characteristic can be harnessed for environmental applications, such as the degradation of pollutants and the development of eco-friendly processes.
Used in Pharmaceutical Research:
As a metabolite of Quinalphos, 2-Quinoxalinone has been found to exhibit genotoxic effects on both lightand dark-exposed bacteria. This property makes it a valuable compound for studying the mechanisms of genotoxicity and the development of new drugs and therapies targeting bacterial infections.
Used in Chemical Coupling Reactions:
2-Quinoxalinone is utilized in direct dehydrative cross-coupling reactions with other organic compounds, such as p-tolylacetylene, via Pd/Cu-catalyzed phosphonium coupling. This reaction provides a convenient and efficient method for the synthesis of complex organic molecules with potential applications in various industries.

InChI:InChI=1/C8H6N2O/c11-8-5-9-6-3-1-2-4-7(6)10-8/h1-5H,(H,10,11)

Upstream product

• 6935-29-1 quinoxaline-N-oxide 
• 53374-52-0 1-nitroso-3-keto-1,2,3,4-tetrahydroquinoxaline 
• 302-17-0 chloral hydrate 
• 39145-59-0 o-phenylenediamine hydrochloride 
• 924-44-7 glyoxylic acid ethyl ester 
• 95-54-5 1,2-diamino-benzene 
• 57987-56-1 1,2-diethoxy-1,2-dichloro-ethane 
• 6295-06-3 butyl glyoxalate 
• 2810-42-6 N,N'-bis(chloroacetyl)-o-phenylenediamine 
• 106-49-0 p-toluidine 
• 59564-59-9 1,2,3,4-tetrahydroquinoxalin-2-one 
• 98-86-2 acetophenone 
• 67-64-1 acetone 
• 78-93-3 butanone 

Downstream Products

• 6479-18-1 1-methyl-2(1H)-quinoxalinone 
• 1448-87-9 2-chloroquinoxaline 
• 15804-19-0 quinoxaline-2,3-dione 
• 60943-26-2 3-[2-(2-Methoxy-phenyl)-2-oxo-ethyl]-1H-quinoxalin-2-one 
• 14003-37-3 3-(2-oxopropyl)-2(1H)-quinoxalinone 
• 35676-70-1 3-chloro-quinoxaline-2(1H)-one 
• 17508-35-9 3,4-dihydro-3-oxoquinoxaline-1-oxide 
• 90703-60-9 6-iodo-2(1H)-quinoxalinone 
• 82031-32-1 7-bromo-1H-quinoxalin-2-one 
• 55687-34-8 6-bromoquinoxalin-2(1H)-one 
• 13593-03-8 quinalphos 
• 36856-91-4 2-bromo-quinoxaline 
• 2213-63-0 2,3-dichloroquinoxaline 
• 39209-88-6 2-methoxy-quinoxaline 

Relevant articles and documents

Iodine-Catalyzed Oxidative Cross-Dehydrogenative Coupling of Quinoxalinones and Indoles: Synthesis of 3-(Indol-2-yl)quinoxalin-2-one under Mild and Ambient Conditions

A highly efficient iodine-catalyzed oxidative cross-dehydrogenative coupling reaction of quinoxalinones and indoles has been developed. Without the requirement of peroxide and acid, this reaction utilizes a catalytic amount of molecular iodine to facilitate the C-C bond formation under ambient air. This simple and easy-to-handle protocol represents an interesting synthetic alternative with a good scope and functional group compatibility.

Micellar effects upon the reaction of hydroxide ion with 2-phenoxyquinoxaline

Cationic micelles of alkyltrimethylammonium chloride and bromide (alkyl = n - C12H25, n - C14H29, and n - C16H33) catalyze and anionic micelles of sodium dodecyl sulfate inhibit the reaction of hydroxide ion with 2-phenoxyquinoxaline (1). Inert anions such as chloride, nitrate, mesylate, and n-butanosulfonate inhibit the reaction in CTABr by competing with OH- at the micellar surface. The overall micellar effects on rate in cationic micelles and dilute electrolyte can be treated quantitatively in terms of the pseudo-phase ion-exchange model. The determined second-order rate constants in the micellar pseudo-phase are smaller than the second-order constants in water.

Synthesis of 2-(4-nitrophenoxy)quinoxaline and its reactions with hydroxide ion in micellar systems

The synthesis of 2-(4-nitrophenoxy)quinoxaline (3) is described. The reaction of (3) with hydroxide ion was studied in the presence and absence of micellar systems. Cationic micelles of cetyltrimethylammonium chloride and bromide (CTACl and CTABr) and tetradecyltrimethylammonium chloride and bromide (MTACl and MTABr) speed the reaction of (3) with hydroxide ion. The second-order rate constants at the micellar pseudophase are smaller than the second-order rate constant in water.

Chemoselective synthesis of 3,6,7-trisubstituted 2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyloxy]- and 2-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)quinoxaline derivatives

[Figure not available: see fulltext.] A series of quinoxaline O-nucleosides, 3,6,7-trisubstituted 2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl-1-yl)quinoxalines and 2-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)quinoxalines, was prepared by the reaction of 3,6,7-trisubstituted quinoxalin-2(1H)-ones with the corresponding protected α-chlorosugars in the presence of NaH. The reaction proceeded chemoselectively to give products of O-substitution with β-configuration at anomeric carbon, as proved by NMR data. The deprotection of the 1-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)quinoxalines was achieved by stirring in ammonia-methanol mixture to afford free O-quinoxaline nucleoside analogs.

Synthesis of (E)-Quinoxalinone Oximes through a Multicomponent Reaction under Mild Conditions

Herein, a novel method for the gram-scale synthesis of (E)-quinoxalinone oximes through a multicomponent reaction under mild conditions is described. Such a transformation was performed under transition-metal-free conditions, affording (E)-oximes in a moderate-to-good yield through recrystallization. Our methodology demonstrates a successful combination of a Mannich-type reaction and radical coupling, providing a green and practical approach for the synthesis of potentially bioactive quinoxalinone-containing molecules.

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.

Tosvinyl and besvinyl as protecting groups of imides, azinones, nucleosides, sultams, and lactams. Catalytic conjugate additions to tosylacetylene

The use of the 2-(4-methylphenylsulfonyl)-ethenyl (tosvinyl, Tsv) group for the protection of the NH group of a series of imides, azinones (including AZT), inosines, and cyclic sulfonamides has been examined. The Tsvprotected derivatives are obtained in excellent yields by conjugate addition to tosylacetylene (ethynyl p-tolyl sulfone). The stereochemistry of the double bond can be controlled at will: with only 1 mol % of Et3N or with catalytic amounts of NaH, the Z stereoisomers are generated almost exclusively, while the E isomers are obtained using a stoichiometric amount of DMAP. Analogous phenylsulfonylvinyl-protected groups (with the besvinyl or Bsv group instead of Tsv) are obtained stereospecifically by reaction with (Z)- or (E)-bis(phenylsulfonyl)ethene. For lactams and oxazolidinones, this last method is much better. The Tsv and Bsv groups are stable in the presence of non-nucleophilic bases and to acids. They can be removed highly effectively via a conjugate addition-elimination mechanism using pyrrolidine or sodium dodecanethiolate as nucleophiles.

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.

UNPRODUCTIVE SIGMA AND PI COMPLEXES IN THE REACTION OF 2-CHLOROQUINOXALINE WITH PIPERIDINE IN DIMETHYL SULPHOXIDE

The rate of the reaction of 2-chloroquinoxaline with piperidine in dimethyl sulphoxide was measured over a wide range of amine concentrations and at several temperatures.It was found that the order with respect to the nucleophile is close to 1 between 300 and 320 K, but is definitely less at lower and higher temperatures.It is suggested that below 300 K an unreactive charge-transfer complex is formed between the reactants which dissociates at higher temperatures, whereas at temperatures higher than 320 K an unproductive ? complex is formed, the concentration of which increases with increase in temperature.

Surfactant effects on the reaction of 2-(4-cyano-phenoxy)-quinoxaline with hydroxide ion

A reaction of 2-(4-cyanophenoxy)quinoxaline 1 with hydroxide ion is accelerated by supramolecular aggregates of cetyltrialkylammonium chlorides (alkyl = Me. n-Pr. and n-Bu). In diluted surfactant solutions, with relatively high substrate concentration (7.0 × 10-5 M). rate constants go through double rate maxima with increase in the surfactant concentration. The first rate maximum is ascribed to a reaction occurring in premicellar aggregates and the second to reaction in micelles. At low substrate concentration (7×10-6 M), second-order rate constants in the micellar pseudophase are dependent on the surfactant head-group size, which is related to charge dispersion in the transition state. Nonmicellizing tri-n- octylmethylammonium ions (TOAMs) increase the reaction of 1 with hydroxide ion. The observed rate enhancements may be due to the formation of small. Hydrophobic aggregates which bind the substrate and promote the nucleophilic substitution reaction.