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== <!--This article uses the Cite.php citation mechanism. If you would like more information on how to add references to this article, please see http://meta.wikimedia.org/wiki/Cite/Cite.php --> <div class="references-small" style="-moz-column-count:2; column-count:2;"> <references/> </div> [[Category:Cycloalkenes|Cyclohexadiene, 1,3-]] {{hydrocarbon-stub}} {{cycloalkenes}} [[vi:1,3-Cyclohexadien]]