158871-28-4

Basic information

• Product Name: 4,5-BIS(2-CYANOETHYLTHIO)-1,3-DITHIOL-2-ONE
• Synonyms: RARECHEM AR PA 0056;4,5-BIS(2-CYANOETHYLTHIO)-1,3-DITHIOL-2-;4,5-BIS(2''-CYANOETHYLTHIO)-1,3-DITHIOLE-2-ONE 97%;4,5-BIS(2-CYANOETHYLTHIO)-1,3-DITHIOL-2-ONE;4,5-BIS(2'-CYANOETHYLTHIO)1-3-DITHIOL-2-ONE;4,5-BIS(2'-CYANOETHYLTHIO)-1,3-DITHIOLE-2-ONE
• CAS NO: 158871-28-4
• Molecular Formula: C₉H₈N₂OS₄
• Molecular Weight: 288.43
• Product Categories: Sulphur Derivatives;Heterocyclic Compounds;Charge Transfer Complexes (Synthetic Intermediates);Charge Transfer Complexes for Organic Metals;Functional Materials
• Mol File: 158871-28-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 84-87 °C(lit.)
• Boiling Point: 511.6°C at 760 mmHg
• Flash Point: 263.2°C
• Appearance: /
• Density: 1.49g/cm³
• Vapor Pressure: 1.4E-10mmHg at 25°C
• Refractive Index: 1.684
• CAS DataBase Reference: 4,5-BIS(2-CYANOETHYLTHIO)-1,3-DITHIOL-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-BIS(2-CYANOETHYLTHIO)-1,3-DITHIOL-2-ONE(158871-28-4)
• EPA Substance Registry System: 4,5-BIS(2-CYANOETHYLTHIO)-1,3-DITHIOL-2-ONE(158871-28-4)

Safety Data

• RIDADR: UN 3439 6.1/PG III
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 158871-28-4(Hazardous Substances Data)

Usage

General Description

4,5-BIS(2-CYANOETHYLTHIO)-1,3-DITHIOL-2-ONE is a chemical compound with the molecular formula C10H8N2S2O2. It is a dithiolone derivative with two cyanoethylthio groups attached to a 1,3-dithiol-2-one ring. 4,5-BIS(2-CYANOETHYLTHIO)-1,3-DITHIOL-2-ONE is commonly used in organic synthesis as a reagent for the preparation of various organic compounds. It has also been studied for its potential biological activities, including its antimicrobial and antiviral properties. Additionally, 4,5-BIS(2-CYANOETHYLTHIO)-1,3-DITHIOL-2-ONE has been investigated for its potential use in the development of new materials with specific functional properties.

InChI:InChI=1/C9H8N2OS4/c10-3-1-5-13-7-8(14-6-2-4-11)16-9(12)15-7/h1-2,5-6H2

Upstream product

• 132765-35-6 4,5-bis((2-cyanoethyl)thio)-1,3-dithiole-2-thione 
• 1600-27-7 mercury(II) diacetate 
• 72022-68-5 bis(tetraethylammonium)bis(2-thioxo-1,3-dithiole-4,5-dithiolate)zincate 

Downstream Products

• 132765-36-7 2,3,6,7-tetrakis(2-cyanoethylthio)tetrathiafulvalene 
• 1204138-61-3 2,3-bis(2-cyanoethylthio)-6,7-bis(3,5-di-tert-butylbenzylthio)-1,4,5,8-tetrathiafulvalene 
• 891848-04-7 tetracyanodibenzotetrathiafulvalene 
• 1604841-94-2 C₄₄H₃₄N₈O₂S₁₂ 
• 97942-32-0 bis-(pyrazino)-tetrathiafulvalene 
• 186139-70-8 4,5-bis(2-cyanoethylsulfanyl)tetrathiafulvalene 
• 1389330-60-2 2,3-bis[2-(2-tosyloxyethoxy)ethylsulfanyl]-6,7-bis(methylthio)tetrathiafulvalene 
• 1321625-06-2 2-[4,5-bis(2-cyanoethylthio)-1,3-dithiol-2-ylidene]-5-(3,5-di-tert-butylbenzyl)-5H-1,3-dithiolo[4,5-c]pyrrole 
• 232587-08-5 C₆₈H₆₈N₆O₁₀S₁₆ 
• 232587-07-4 C₆₃H₅₈N₆O₉S₁₆ 

Relevant articles and documents

Fabrication and operation of monolayer mott FET at room temperature

Self-assembled monolayer FET based on a TTF derivative is described (FET = field-effect-transistor, TTF = tetrathiafulvalene). The molecule is anchored on an alumina dielectric layer through covalent bonding of a phosphonic acid linker. A p-type monolayer FET device is achieved and subsequent chemical doping of this monolayer with F4TCNQ dopants results in an ambipolar device. (F4TCNQ = 2,3,5,6-Tetrafluoro- 7,7,8,8-tetracyanoquinodimethane) Several strange behaviors including a gate voltage shift upon doping seem to be consistent with organic monolayer Mott FET. Finally, temperature dependence of the FET performance, which also fit the anticipated Mott FET behavior, is discussed.

Luminescence switching of a cyclometalated iridium(III) complex through a redox-active tetrathiafulvalene-based ligand

A tetrathiafulvalene (TTF) moiety through an acetyl acetonate bridge to a phosphorescent Iridium (Ir) core with a luminescent active MLCT excited state to observe redox controlled electronic coupling between the inorganic metal luminophore and TTF spacer through distinct luminescent behaviours has been reported. The TTF structure was confirmed by mass spectrometry and NMR spectrocopy. The phosphorescence property of complexes can be modulated by ET-acac ligand, which exhibits different photo-induced electron transfer efficiencies of TTF in distinct oxidation states. The target compound may serve as a novel model compound to investigate the mechanism of charge transfer between Ir based luminescent layer and conductive layer, such as derivative, in OLED materials. The singlet-triplet interactions at excited states contribute to the dynamic π-d coupling in TTF-based metal compounds.

Synthesis, structure and electrochemical properties of two new unsymmetrical tetrathiafulvalene derivatives

Two new unsymmetrical tetrathiafulvalene (TTF) derivatives, 2,3-bis(cyanoethylthio)-6,7-(methylethylenedithio)tetrathiafulvalene (6a) and 2,3-bis(cyanoethylthio)-6,7-(cyclopentodithio)tetrathiafulvalene (6b), have been prepared and characterized by NMR, MS, IR and Elemental analyses. The molecular structures have been determined by X-ray crystallography. Their redox properties have been investigated by cyclic voltammetry in dichloromethane solution and each compound shows two reversible single-electron redox couples.