Cyclooctatetraene

1,3,5,7-Cyclooctatetraene (COT) is an unsaturated derivative of cyclooctane, with the formula C8H8. It is also known as [8]annulene. This polyunsaturated hydrocarbon is a colorless to light yellow flammable liquid at room temperature. Because of its stoichiometric relationship to benzene, COT has been the subject of much research and some controversy.

Cyclooctatetraene
Names
Preferred IUPAC name
Cycloocta-1,3,5,7-tetraene
Other names
[8]Annulene
(1Z,3Z,5Z,7Z)-Cycloocta-1,3,5,7-tetraene
1,3,5,7-Cyclooctatetraene
COT
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.074
EC Number
  • 211-080-3
PubChem CID
UNII
  • InChI=1S/C8H8/c1-2-4-6-8-7-5-3-1/h1-8H/b2-1-,3-1-,4-2-,5-3-,6-4-,7-5-,8-6-,8-7- Y
    Key: KDUIUFJBNGTBMD-BONZMOEMSA-N Y
  • InChI=1/C8H8/c1-2-4-6-8-7-5-3-1/h1-8H/b2-1-,3-1-,4-2-,5-3-,6-4-,7-5-,8-6-,8-7-
    Key: KDUIUFJBNGTBMD-BONZMOEMBR
SMILES
  • C1=C\C=C/C=C\C=C1
Properties
C8H8
Molar mass 104.15 g/mol
Appearance Clear yellow
Density 0.9250 g/cm3, liquid
Melting point −5 to −3 °C (23 to 27 °F; 268 to 270 K)
Boiling point 142 to 143 °C (288 to 289 °F; 415 to 416 K)
immiscible
Magnetic susceptibility (χ)
 -53.9·10−6 cm3/mol
Hazards
GHS labelling:
Danger
H225, H304, H315, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P331, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
3
3
0
Flash point −11 °C (12 °F; 262 K)
561 °C (1,042 °F; 834 K)
Related compounds
Related hydrocarbons
 Cyclooctane
Tetraphenylene
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

Unlike benzene, C6H6, cyclooctatetraene, C8H8, is not aromatic, although its dianion, C
8H2−
8 (cyclooctatetraenide), is. Its reactivity is characteristic of an ordinary polyene, i.e. it undergoes addition reactions. Benzene, by contrast, characteristically undergoes substitution reactions, not additions.

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