Tetrathiafulvalene

Tetrathiafulvalene
Names
	Preferred IUPAC name 2,2′-Bi(1,3-dithiolylidene)
	Other names Δ2,2-Bi-1,3-dithiole
Identifiers
CAS Number	31366-25-3 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1282106
ChEBI	CHEBI:52444 ;
ChemSpider	89848 ;
ECHA InfoCard	100.045.979
EC Number	250-593-7;
PubChem CID	99451;
UNII	HY1EN16W9T ;
CompTox Dashboard (EPA)	DTXSID6067620 ;
	InChI InChI=1S/C6H4S4/c1-2-8-5(7-1)6-9-3-4-10-6/h1-4H Key: FHCPAXDKURNIOZ-UHFFFAOYSA-N ; InChI=1/C6H4S4/c1-2-8-5(7-1)6-9-3-4-10-6/h1-4H Key: FHCPAXDKURNIOZ-UHFFFAOYAZ;
	SMILES S1C=CSC1=C2SC=CS2;
Properties
Chemical formula	C6H4S4
Molar mass	204.34 g·mol−1
Appearance	Yellow solid
Melting point	116 to 119 °C (241 to 246 °F; 389 to 392 K)
Boiling point	Decomposes
Solubility in water	Insoluble
Solubility in organic solvents	Soluble[vague]
Structure
Dipole moment	0 D
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	combustible
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H317
Precautionary statements	P261, P280, P302+P352, P333+P313, P363, P501
Related compounds
Related compounds	TCNQ; Thiophene; Tetracyanoethylene;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Tetrathiafulvalene (TTF) is an organosulfur compound with the formula (C₃H₂S₂)₂. Studies on this heterocyclic compound contributed to the development of molecular electronics. TTF is related to the hydrocarbon fulvalene, (C₅H₄)₂, by replacement of four CH groups with sulfur atoms. Over 10,000 scientific publications discuss TTF and its derivatives.^[2]

^ "Tetrathiafulvalene". pubchem.ncbi.nlm.nih.gov.
^ Bendikov, M; Wudl, F; Perepichka, D F (2004). "Tetrathiafulvalenes, Oligoacenenes, and Their Buckminsterfullerene Derivatives: The Brick and Mortar of Organic Electronics". Chemical Reviews. 104 (11): 4891–4945. doi:10.1021/cr030666m. PMID 15535637.

[1] "Tetrathiafulvalene". pubchem.ncbi.nlm.nih.gov.

[Bendikov-2] Bendikov, M; Wudl, F; Perepichka, D F (2004). "Tetrathiafulvalenes, Oligoacenenes, and Their Buckminsterfullerene Derivatives: The Brick and Mortar of Organic Electronics". Chemical Reviews. 104 (11): 4891–4945. doi:10.1021/cr030666m. PMID 15535637.

[1]

[2]