1199-03-7

Usage

Purification Methods

Purify the dithiol by repeated dissolution in alkali and re-precipitation by acetic acid. It complexes with Ag+, Cd2+ , Pb2+ , Bi3+ and Ni2+ in aqueous NH3. [Beilstein 24 III/IV 1428.]

InChI:InChI=1/C8H6N2S2/c11-7-8(12)10-6-4-2-1-3-5(6)9-7/h1-4H,(H,9,11)(H,10,12)

Upstream product

• 2213-63-0 2,3-dichloroquinoxaline 
• 17356-08-0 thiourea 
• 15804-19-0 quinoxaline-2,3-dione 
• 15804-19-0 2,3-dihydroxyquinoxaline 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 76261-60-4 2,3-bis(methylthio)quinoxaline 
• 73029-86-4 2,3-bis(hydrazino)quinoxaline 
• 13080-21-2 2-mercapto-3-hydrazinoquinoxaline 
• 86843-76-7 2-[3-(2-Oxo-2-phenyl-ethylsulfanyl)-quinoxalin-2-yl]-1-phenyl-ethanone 
• 84609-55-2 1-Phenyl-2-(2-phenyl-[1,3]dithiolo[4,5-b]quinoxalin-2-yl)-ethanone 

Relevant academic research and scientific papers

Synthesis and structure of the first ribbed-functionalized quinoxaline clathrochelate: Design of cage complexes for efficient intercalation into DNA structure

Condensation of the dichloride clathrochelate FeBd2(Cl 2Gm)(BF)2 precursor (Bd2- is the α-benzyl dioxime dianion, Gm is the glyoxime residue) with quinoxaline-2,3-dithiol in the presence of triethylamine afforded the ribbed-functionalized quinoxaline clathrochelate. The structure of this complex was established by X-ray diffraction analysis.

A family of molecular nickel hydrogen evolution catalysts providing tunable overpotentials using ligand-centered proton-coupled electron transfer paths

Two new nickel dithiolate derivatives have been examined for their electrocatalytic activity for the hydrogen evolution reaction (HER) in attempts to clarify whether the overpotential for the HER can be tuned upon varying the ligand-centered reduction potential that triggers the HER by the catalysts. We demonstrate the validity of this approach to achieve desirable tunability in the overpotential for the HER.

Thionations using a P4S10-pyridine complex in solvents such as acetonitrile and dimethyl sulfone

Tetraphosphorus decasulfide (P4S10) in pyridine has been used as a thionating agent for a long period of time. The moisture-sensitive reagent has now been isolated in crystalline form, and the detailed structure has been determined by X-ray crystallography. The thionating power of this storable reagent has been studied and transferred to solvents such as acetonitrile in which it has proven to be synthetically useful and exceptionally selective. Its properties have been compared with the so-called Lawesson reagent (LR). Particularly interesting are the results from thionations at relatively high temperatures (165 °C) in dimethyl sulfone as solvent. Under these conditions, for instance, acridone and 3-acetylindole could quickly be transformed to the corresponding thionated derivatives. Glycylglycine similarly gave piperazinedithione. At these temperatures, LR is inefficient due to rapid decomposition. The thionated products are generally cleaner and more easy to obtain because in the crystalline reagent, impurities which invariably are present in the conventional reagents, P4S 10 in pyridine or LR, have been removed. 2011 American Chemical Society.

Synthesis of novel oxidizable polymerization sensitizers based on the dithiinoquinoxaline skeleton

Novel dyes, based on the dithiinoquinoxaline skeleton, were synthesized and characterized using 1H NMR spectroscopy and chemical ionization mass spectroscopy. Their spectral properties, such as absorption, emission spectra and quantum yield of fluorescence, were also measured. Electron donating properties of the title compounds were estimated on the basis of DFT calculations. The studied dyes were used as oxidizable sensitizers for 2,4,6-tris(trichloromethyl)-1,3,5-triazine (Tz). The dye/Tz photoredox pairs were found to be effective visible-wavelength initiators of free radical polymerization. The ability of these systems to act as photoinitiators strongly depended upon the free energy change of the photoinduced electron transfer from the excited dyes to Tz. It has been shown that the intermolecular electron transfer is the limiting step in the photopolymerization initiated by these studied initiator systems.

A novel method for heterocyclic amide-thioamide transformations

In this paper, we introduce a novel and convenient method for the transformation of heterocyclic amides into heteocyclic thioamides. A two-step approach was applied for this transformation: Firstly, we applied a chlorination of the heterocyclic amides to afford the corresponding chloroheterocycles. Secondly, the chloroherocycles and N-cyclohexyl dithiocarbamate cyclohexylammonium salt were heated in chloroform for 12 h at 61°C to afford heteocyclic thioamides in excellent yields.

A THIONATION PROCESS AND A THIONATING AGENT

A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N

A thionation process and a thionating agent

A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N.

Efficient diverse approach for quinoxaline-derived glycosylated and morphinylated analogs

Sulfanyl-glycosides have been synthesized by reaction of 2,3-dimercaptoquinoxaline (1) with acetohalo sugars in presence of base to give the thioglycosides-derived quinoxalines 5-7 and 9. Similarly, the acyclic analogs 23-26 were prepared by coupling of 1 with different acyclo-alkylating agents. The preparation of 3-morpholinyl-quinoxalines 10 and 11 allowed the synthesis of 3-glycosylsulfanyl-2-morpholinyl-quinoxalines 12-14 and 17 as well as the acyclic analogs 27-29. Microwave irradiation of the reactants turned out to be preferred over the conventional method for achieving the synthetic goals. This study made an available venue to the synthesis of diverse quinoxaline derivatives.

Synthesis of novel diphenylamine-based fluorescent styryl colorants and study of their thermal, photophysical, and electrochemical properties

Three novel "Y"-shaped acceptor-π-donor-π-acceptor-type compounds were synthesized from 4,4′-(hexylimino)bis(benzaldehyde) as a donor and 2-methylthiazolo[4,5-b]quinoxaline derivatives as strong electron acceptors condensed by classical Knoevenagel condensation. Their absorption, emission, and thermal properties and electrochemical stability were investigated. It was found that the strong electron acceptor-donor chromophoric system of these compounds showed high Stokes shift, excellent thermal stability, and electrochemical reversibility. The solvatochromic behavior of these colorants was studied by using various solvents such as toluene, chloroform, ethyl acetate, tetrahydrofuran, methanol, and N,N-dimethylformamide in increasing order of polarity. The dyes were characterized by means of elemental analysis, 1H NMR, and mass spectrometry. Springer-Verlag 2010.

ESR-Untersuchungen an Thioamiden, 8. Radikalanionen der Imidazolidintrione, Piperazindione, Piperazintetraone und Chinoxalindione sowie ihrer Schwefel-Analoga.

Cyclische Oxamid-Derivate vom Typ des Imidazolidin-4,5-dions, Piperazin-2,3-dions, Piperazin-2,3,5,6-tetraons und Chinoxalin-2,3-dions sowie Thio-Analoga und mit 2H, 13C oder 15N markierte Vertreter werden dargestellt und durch in-situ-Elektroreduktion in die entsprechenden Radikalanionen uebergefuehrt.Aus deren isotropen und anisotropen ESR-Spektren sowie einer Analyse der Linienbreite und Linienform wird die Spindichteverteilung ermittelt und anhand MO-theoretisch berechneter Werte diskutiert.