Tetrathiafulvalene

Base Information

• Chemical Name: Tetrathiafulvalene
• CAS No.: 31366-25-3
• Deprecated CAS: 143413-93-8,56243-32-4,56481-75-5,87891-32-5,56243-32-4,56481-75-5,87891-32-5
• Molecular Formula: C6H4 S4
• Molecular Weight: 204.362
• Hs Code.: 29309090
• European Community (EC) Number: 250-593-7
• NSC Number: 222862
• UNII: HY1EN16W9T
• DSSTox Substance ID: DTXSID6067620
• Nikkaji Number: J316F
• Wikipedia: Tetrathiafulvalene
• Wikidata: Q2179180
• Metabolomics Workbench ID: 58264
• Mol file: 31366-25-3.mol

Synonyms:1,4,5,8-tetrathiafulvalene;2-(1,3-dithiol-2-ylidene)-1,3-dithiole;bis-1,3-dithiole;delta-2,2'-bi-1,3-dithiole;NSC-222862;tetrathiafulvalene

Chemical Property of Tetrathiafulvalene

Chemical Property:

• Vapor Pressure: 0.107mmHg at 25°C
• Melting Point: 116-119 °C(lit.)
• Refractive Index: 1.879
• Boiling Point: 229°Cat760mmHg
• Flash Point: 120.9°C
• PSA: 101.20000
• Density: 1.636g/cm³
• LogP: 4.01540
• Storage Temp.: 2-8°C
• Sensitive.: Air & Light Sensitive
• Water Solubility.: It is insoluble in water. Soluble in organic solvents.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 203.91958482
• Heavy Atom Count: 10
• Complexity: 182

Purity/Quality:

98%,99%, ^*data from raw suppliers

Tetrathiafulvalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43-52/53
• Safety Statements: 36/37-61-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: C1=CSC(=C2SC=CS2)S1
• Uses: Electron donor for supramolecular synthesis,1 charge-transfer complex synthesis2 with 7,7,8,8-tetracyanoquinodimethane (cat. no. 157635), and for electron transfer to diazonium salts.3 Molecular sensors; radical catalyst. Tetrathiafulvalene, holds wide application in HPLC, NMR. This heterocyclic compound contributed to the development of molecular electronics. They are used as a organic super conductors.

Technology Process of Tetrathiafulvalene

There total 51 articles about Tetrathiafulvalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

4-bromotetrathiafulvalene (57223-41-3) → tetrathiafulvalene (31366-25-3)

Guidance literature:

With n-butyllithium; In diethyl ether; for 3h; Heating;

DOI:10.3987/R-1986-04-1145

Reference yield: 99.0%

1,4,5,8-tetrathianaphthalene (255-55-0) → tetrathiafulvalene (31366-25-3)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; for 0.5h; Heating;

Reference yield: 90.0%

1,3-Dithiolium iodide (1863-66-7) + triphenyl[4,5-bis(2'-cyanoethylsulfanyl)-1,3-dithiol-2-yl]phosphonium tetrafluoroborate → tetrathiafulvalene (31366-25-3) + 4,5-bis(2-cyanoethylsulfanyl)tetrathiafulvalene (186139-70-8)

Guidance literature:

With triethylamine; In acetonitrile; at 0 - 5 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tet.2016.08.001

upstream raw materials:

1,3-dithiol-2-one

4,5-ethylenedioxy-1,3-dithiole-2-thione

1,3-dithiol-2-thione

4,5-Ethylenedithio-1,3-dithiole-2-thione

Downstream raw materials:

tetrathiafulvalenium radical cation

7,7,8,8-tetracyanoquinodimethane radical anion

tetrathiafulvalene 7,7,8,8-tetracyanoquinodimethane salt

C₂₇H₁₈S₁₅

Refernces

• 1、 Tatemitsu, Hitoshi,Nishikawa, Etsushi,Sakata, Yoshiteru,Misumi, Soichi. "Synthesis of Unsymmetrical Tetrathiafulvalenes and Electrical Conductivities of Their Tetracyanoquinodimethane Complexes". . p. 106 - 107. Retrieved 1985.
• 2、 Wudl et al.. "". . p. 3608. Retrieved 1974.
• 3、 Gemmer et al.. "". . p. 3544,3546, 3547. Retrieved 1975.
• 4、 Marouille, J.Y. Le,Lelay, C.,Benoit, A.,Grandjean, D.,Touchard, D.,at al.. "SULFUR-CONTAINING CARBENE-METAL COMPOUNDS: GENERAL ROUTE FROM CARBON DISULFIDE MANGANESE COMPLEXES; X-RAY STRUCTURE OF 1,3-DITHIOL-2-YLIDENEMANGANESE(I) DERIVATIVE". . p. 133 - 142. Retrieved 1980.
• 5、 Callaghan, Owen,Franck, Xavier,Murphy, John A.. "Unprecedented electrophilic behaviour of tetrathiafulvalenium salts". . p. 1923 - 1924. Retrieved 1997.
• 6、 Bespalov et al.. "". . . Retrieved 1976.
• 7、 Kato, Reizo,Kobayashi, Hayao,Kobayashi, Akiko. "Dimensionality Examination of Cation Radical Salts Based on EDT-TTF (EDT-TTF = Ethylenedithiotetrathiafulvalene)". . p. 781 - 784. Retrieved 1989.
• 8、 Iida, Yoichi. "One-electron Reduction Potentials of Several Electron Acceptor Molecules and Cation Radicals of Donors". . p. 2673 - 2674. Retrieved 1980.
• 9、 Moore, Adrian J.,Bryce, Martin R.. "Tetrathiafulvalene: A convenient large-scale (20 g) synthesis". . p. 407 - 409. Retrieved 1997.
• 10、 Wudl,Kaplan. "". . p. 27,31. Retrieved 1979.