1,3-Cyclohexadiene
1077465
225808353
2008-07-15T14:32:33Z
128.253.43.48
[[WP:UNDO|Undid]] revision 225808013 by [[Special:Contributions/128.253.43.48|128.253.43.48]] ([[User talk:128.253.43.48|talk]])
{{Chembox new
| ImageFile = 1-3-cyclohexadiene.png
| ImageSize = 240px
| IUPACName = Cyclohexa-1,3-diene
| OtherNames = 1,3-Cyclohexadiene, 1,2-Dihydrobenzene, 1,3-CHD
| Section1 = {{Chembox Identifiers
| CASNo = 592-57-4
| PubChem = 11605
| SMILES = C1CC=CC=C1
| InChI = 1/C6H8/c1-2-4-6-5-3-1/h1-4H,5-6H2
| RTECS = GU4702350
| ChEBI = 37610
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>6</sub>H<sub>8</sub>
| MolarMass = 80.13 g/mol
| Appearance = Colourless liquid
| Density = 0.841 g/cm³
| MeltingPt = -98 °C
| BoilingPt = 80 °C
| Solubility =
}}
| Section7 = {{Chembox Hazards
| EUClass = Flammable ('''F''')
| MainHazards =
| RPhrases = {{R11}}
| SPhrases = {{S9}}, {{S16}}, {{S29}}, {{S33}}
| FlashPt = 26 °C c.c.
| Autoignition =
}}
}}
'''1,3-Cyclohexadiene''' is a highly [[flammable]] [[cycloalkene]] that occurs as a colorless clear liquid. Its refractive index is 1.475 (20 °C, D).
It can be used as a hydrogen donor in [[transfer hydrogenation]], since its conversion to benzene + hydrogen is in fact exothermic (-24.3 kJ/mol in the gas phase, as indicated by heats of hydrogenation).<ref name="NIST_Cyclohexadiene">{{cite web|url=http://webbook.nist.gov/cgi/cbook.cgi?ID=C592574&Units=SI&Mask=8#Thermo-React|title=1,3-Cyclohexadiene|publisher=US National Institute of Standards and Technology|date=2007-04-13|accessdate=2007-04-13}}</ref><ref name="NIST_Benzene">{{cite web|url=http://webbook.nist.gov/cgi/cbook.cgi?ID=C71432&Units=SI&Mask=8&StartReac=50#Thermo-React|title=Benzene|publisher=US National Institute of Standards and Technology|date=2007-04-13|accessdate=2007-04-13}}</ref> Despite this apparent instability with respect to benzene, the 1,3-cyclohexadiene motif is found in several natural products such as α-[[terpinene]].
==See also==
* [[Benzene]]
* [[Cyclohexane]]
* [[1,2-Cyclohexadiene]]
* [[1,4-Cyclohexadiene]]
* [[Cyclohexene]]
==References==
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[[Category:Cycloalkenes|Cyclohexadiene, 1,3-]]
{{hydrocarbon-stub}}
{{cycloalkenes}}
[[vi:1,3-Cyclohexadien]]