66946-48-3

Basic information

• Product Name: BIS(ETHYLENEDITHIO)TETRATHIAFULVALENE
• Synonyms: BIS-ETHYLENDITHIO-TETRATHIAFULVALENE;BI[5,6-DIHYDRO-1,3-DITHIOLO[4,5-B][1,4]-DITHIINE-2-YLIDENE];BIS(ETHYLENEDITHIO)TETRATHIAFULVALENE, 9 8%;Bis(ethylenedithia)tetrathiafulvalene;BEDT-TIF;Bis(ethylenedithio)tetrathiafulvalene [Organic Electronic Material];BEDT-TTF, Bi[5,6-dihydro-1,3-dithiolo[4,5-b][1,4]-dithiine-2-ylidene];2-(5,6-Dihydro-1,3-dithiolo[4,5-b][1,4]dithiin-2-ylidene)-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiin
• CAS NO: 66946-48-3
• Molecular Formula: C₁₀H₈S₈
• Molecular Weight: 384.69
• Product Categories: Sulphur Derivatives;Donors (Charge Transfer Complexes);TTF Derivatives;Charge Transfer Complexes for Organic Metals;Functional Materials
• Mol File: 66946-48-3.mol

Chemical Properties

• Melting Point: ~260 °C (dec.)(lit.)
• Boiling Point: 471.31°C (rough estimate)
• Flash Point: 268.416°C
• Appearance: /Powder
• Density: 1.9349 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Solubility: Soluble in organic solvents.
• BRN: 1653830
• CAS DataBase Reference: BIS(ETHYLENEDITHIO)TETRATHIAFULVALENE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(ETHYLENEDITHIO)TETRATHIAFULVALENE(66946-48-3)
• EPA Substance Registry System: BIS(ETHYLENEDITHIO)TETRATHIAFULVALENE(66946-48-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 8-9-23
• Hazardous Substances Data: 66946-48-3(Hazardous Substances Data)

Usage

Chemical Properties

RED LUSTROUS NEEDLES

Uses

It is used as a component for organic superconductors.

General Description

Bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF) is an organic superconducting polymer that is used as an electron donor with a superconducting transition temperature (Tc) of 10K.

InChI:InChI=1/C10H8S8/c1-2-12-6-5(11-1)15-9(16-6)10-17-7-8(18-10)14-4-3-13-7/h1-4H2

Upstream product

• 930-35-8 1,3-dithiol-2-thione 
• 59089-89-3 4,5-Ethylenedithio-1,3-dithiole-2-thione 
• 74962-29-1 2,5,7,9-tetrathiabicyclo[4.3.0]non-1⁽⁶⁾-en-8-one 
• 53808-62-1 4,5-dimethyl-2-selenoxo-1,3-diselenole 
• 53059-75-9 1,3-Dithiolium tetrafluoroborate 
• 144868-69-9 4,5-bis(p-acetoxybenzylsulfanyl)-1,3-dithiol-2-one 
• 158871-28-4 4,5-bis(2-cyanoethylthio)-1,3-dithiol-2-one 
• 16005-62-2 bis-4,5-(trifluoromethyl)-1,3-dithiole-2-thione 
• 337533-84-3 5-(4'-bromophenyl)-[1,3]dithiolo[4,5-b][1,4]dithiin-2-one 
• 337533-81-0 5-(4'-methoxyphenyl)-[1,3]dithiolo[4,5-b][1,4]dithiin-2-one 
• 625851-31-2 6-(4'-methoxyphenyl)thieno[2,3-d][1,3]dithiol-2-one 
• 337533-79-6 5-phenyl-[1,3]dithiolo[4,5-b][1,4]dithiin-2-one 
• 307543-49-3 5-(tert-butyldiphenylsilyloxymethyl)-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiin-2-one 
• 177544-77-3 5-phenyl-1,3-dithiolo<4,5-b>-1,4-dithiin-2-thione 

Relevant articles and documents

Fluorine segregation in crystalline materials: Structural control and solid-state [2+2] cycloaddition in CF3-substituted tetrathiafulvalene derivatives

The well-known influence of long perfluorinated chains on the structures and stability of amphiphilic molecules in liquid crystalline mesophases or mesoscopic micellar arrangements is evaluated here in the realm of crystalline materials based on rigid aro

An in depth study of the formation of new tetrathiafulvalene derivatives from 1,8-diketones

A detailed study of the reactions of phosphorus pentasulfide and Lawesson's reagent with a series of 4,5-bis(RCOCH 2S)-1,3-dithiole-2-thiones (R=Ph, 4-MeOC6H4, 4-Br C6H4, Me) has been carried out. These reactions lead to fusion of either an unsaturated 1,4-dithiin ring or a thiophene to the dithiole; the former in higher yield, while the latter is a significant product in the reactions with Lawesson's reagent; as well as small amounts of minor products. A mechanistic rationalization of these products is discussed in some detail. The new fused dithioles have been converted to novel series of fused TTF derivatives.

Functionalised organosulfur donor molecules: Synthesis of racemic hydroxymethyl-, alkoxymethyl- and dialkoxymethyl-bis(ethylenedithio)tetrathiafulvalenes

Short synthetic routes to racemic derivatives of bis(ethylenedithio)tetrathiafulvalene carrying one hydroxymethyl (HMET), alkoxymethyl or dialkoxymethyl side chain are reported along with cyclic voltammetry measurements and conversion of HMET to (2:1) radical cation salts.

Electron Transfer from Tetrathiafulvalenes to Photoexcited C70 Studied by Observing Transient Absorption in the Near-IR Region

The photoinduced electron transfer between C70 and tetrathiafulvalene or bis(ethylenedithio)tetrathiafulvalene in polar and nonpolar solvents and their mixture has been investigated by nanosecond laser photolysis/transient absorption spectroscopy in the visible and near-IR regions.The transient absorption bands of the triplet state of C70 observed in polar solvents decayed upon addition of tetrathiafulvalenes accompanied by the appearance of the transient absorption bands of the radical anion of C70.In benzene, the quenching of the triplet state of C70 was observed without the appearance of the radical anion of C70 within a nanosecond laser pulse, suggesting a collisional quenching of the triplet state of C70 with tetrathiafulvalenes.The quantum yield for the formation of the radical anion via the triplet state of C70 was about 1 for tetrathiafulvalene in benzonitrile.The quantum yield decreased in less polar solvents.The back electron transfer rates were also evaluated in polar solvents.

An unusual reaction of Lawesson's reagent with 1,8-diketones: A synthesis of fused 1,4-dithiins and thiophenes

Reaction of 1,8-diketones 3 with Lawesson's reagent 8 resulted in the formation of five and six-membered rings 5-7, 18, depending on the nature of the substituents. Product 6 is converted in two steps to the unsymmetric 'ET' analogue 20, containing an extra double bond.

Synthesis of New 2H-1,3-Dithiol-2-thiones and -2H-1,3-Dithiol-Ones, the Intermediates for Tetrathiafulvalenes and Metal Dithiolates

The synthesis of 2H-1,3-dithiol-2-thiones substituted in positions 4 and 5 was performed by the ring cleavage in 2,5,7,9-tetrathiobicyclonon-1(6)en-3-on-8-thione by sodium methoxide followed by alkylation of the obtained thiolate.The reactions of 2,4,5-tetrahydro-1,3-dithiol-2,4,5-trithione with cyclopentadiene, indene, diethylvinyldithiocarbamate, and allyl bromide, resulting new, earlier unaccessible, 2H-1,3-dithiol-2-thiones were carried out.Synthesis of new 2H-1,3-dithiol-3-thiones with substituents in 4 and 5 positions is performed; some of these compounds were transformed into related diketones by reacting with mercury acetate.New tetrathiofulvalenes are obtained.

Synthesis of Unsymmetrical Tetrakis(alkylsulfanyl)tetrathiafulvalene Derivatives

The p-acetoxybenzylsulfanyl protecting group is compatible with the triethylphosphite mediated cross-coupling of 4,5-bis(alkylsulfanyl)-1,3-dithiol-2-ones, providing access to bis(protected)tetrathiafulvalenes, and thus to tetrathiafulvalenedithiolate dia

Synthesis of New Unsymmetrical Multi-Sulfur TTF Derivatives

Multi-sulfur TTF derivatives with eight or nine sulfur atoms were synthesized for the development of new conducting organic salts.Their oxidation potentials were measured, and compared with those of the related donor molecules.The electrical conductivities of some of the ion radical salts were measured.

4,5-Ethylenedioxy-4',5'-ethylenedithiotetrathiafulvalene (EOET): a New Unsymmetrical Electron Donor

The synthesis, characterization, electrochemical properties, and preliminary X-ray structural data of the title electron donor, a hybrid of bis(ethylenedithio)tetrathiafulvalene and bis(ethylenedioxy)tetrathiafulvalene, are presented.

Unsymmetrically Substituted Ethylenedioxytetrathiafulvalenes

Seven new electron donors, 4,5-ethylenedioxytetrathiafulvalenes where 4',5'-substituents are trimethylenedithio, ethylenedithio, methylenedithio, 2-oxatrimethylenedithio, methylthio, hydrogen and methyl carboxylate, are prepared, and their electrochemical properties are investigated.