Cyclooctatetraene

Cyclooctatetraene
Names
Preferred IUPAC name
Cycloocta-1,3,5,7-tetraene[1]
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 Edit this at Wikidata
EC Number
  • 211-080-3
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- checkY
    Key: KDUIUFJBNGTBMD-BONZMOEMSA-N checkY
  • 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
  • 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
-53.9·10−6 cm3/mol
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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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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.

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.

  1. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. P001–P004. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.