Tetracyanoquinodimethane

Tetracyanoquinodimethane (TCNQ) is an organic compound with the chemical formula (N≡C−)2C=C6H4=C(−C≡N)2. It is an orange crystalline solid. This cyanocarbon, a relative of para-quinone, is an electron acceptor that is used to prepare charge transfer salts, which are of interest in molecular electronics.

Tetracyanoquinodimethane (TCNQ)

Sample of TCNQ
Names
Preferred IUPAC name
2,2′-(Cyclohexa-2,5-diene-1,4-diylidene)dipropanedinitrile
Other names
(2,5-Cyclohexadiene-1,4-diylidene)
-dimalononitrile, 7,7,8,8-Tetracyanoquinodimethane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.014.704
EC Number
  • 216-174-8
UNII
  • InChI=1S/C12H4N4/c13-5-11(6-14)9-1-2-10(4-3-9)12(7-15)8-16/h1-4H Y
    Key: PCCVSPMFGIFTHU-UHFFFAOYSA-N Y
  • InChI=1S/C12H4N4/c13-5-11(6-14)9-1-2-10(4-3-9)12(7-15)8-16/h1-4H
  • c1cc(=C(C#N)C#N)ccc1=C(C#N)C#N
Properties
C12H4N4
Molar mass 204.192 g·mol−1
Appearance green colored powder or orange crystals
Melting point 293.5 to 296 °C (560.3 to 564.8 °F; 566.6 to 569.1 K)
Boiling point Sublimes
Hazards
GHS labelling:
Danger
H302, H311, H312, H331
P261, P264, P270, P271, P280, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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