Cyclooctatetraene
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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.
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Names | |||
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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 | |||
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3D model (JSmol) |
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ChEBI | |||
ChemSpider |
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ECHA InfoCard | 100.010.074 | ||
EC Number |
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PubChem CID |
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UNII | |||
CompTox Dashboard (EPA) |
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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: | |||
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) | |||
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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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.