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
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 H₂C₂S₂C=CS₂C₂H₂. It is the parent of many tetrathiafulvenes. Studies on these heterocyclic compound contributed to the development of molecular electronics, although no practical applications of TTF emerged. TTF is related to the hydrocarbon fulvalene (H₄C₄C=CC₄H₄) by replacement of four CH groups with sulfur atoms. Over 10,000 scientific publications discuss TTF and its derivatives.

Names



Preferred IUPAC name 2,2′-Bi(1,3-dithiolylidene)
Other names Δ^2,2′-Bi-1,3-dithiole
Identifiers
CAS Number	31366-25-3^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1282106
ChEBI	CHEBI:52444^Y
ChemSpider	89848^Y
ECHA InfoCard	100.045.979
EC Number	250-593-7
PubChem CID	99451
UNII	HY1EN16W9T^Y
CompTox Dashboard (EPA)	DTXSID6067620
InChI InChI=1S/C6H4S4/c1-2-8-5(7-1)6-9-3-4-10-6/h1-4H^Y Key: FHCPAXDKURNIOZ-UHFFFAOYSA-N^Y 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
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). Y verify (what is ^YN ?) Infobox references