| Revision as of 14:11, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 462655649 of page 1,3-Cyclohexadiene for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 03:26, 6 November 2024 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,495 edits →Occurrence: ''cis''-1,2-dihydrocatechol. |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 401757105 |
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| verifiedrevid = 477185725 |
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| ImageFile = 1-3-cyclohexadiene.png |
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| ImageFile = 1-3-Cyclohexadiene.svg |
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| ImageSize = 240px |
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| ImageSize1 = 100px |
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| ImageSize = 240px |
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| ImageFileL2 = 1,3-cyclohexadiene-3D-balls.png |
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| ImageSize1 = 100px |
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| ImageFileL2 = 1,3-cyclohexadiene-3D-balls.png |
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| ImageFileR2 = 1,3-cyclohexadiene-3D-vdW.png |
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| ImageFileR2 = 1,3-cyclohexadiene-3D-vdW.png |
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| IUPACName = Cyclohexa-1,3-diene |
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| PIN = Cyclohexa-1,3-diene |
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| OtherNames = 1,3-Cyclohexadiene, 1,2-Dihydrobenzene, 1,3-CHD |
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| OtherNames = 1,3-Cyclohexadiene, 1,2-Dihydrobenzene, 1,3-CHD |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 11117 |
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|ChemSpiderID = 11117 |
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| InChIKey = MGNZXYYWBUKAII-UHFFFAOYAH |
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|InChIKey = MGNZXYYWBUKAII-UHFFFAOYAH |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H8/c1-2-4-6-5-3-1/h1-4H,5-6H2 |
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|StdInChI = 1S/C6H8/c1-2-4-6-5-3-1/h1-4H,5-6H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = MGNZXYYWBUKAII-UHFFFAOYSA-N |
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|StdInChIKey = MGNZXYYWBUKAII-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 592-57-4 |
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|CASNo = 592-57-4 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 11605 |
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|UNII = JV5W0EG5BP |
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| SMILES = C\1=C\C=C/CC/1 |
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|PubChem = 11605 |
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| InChI = 1/C6H8/c1-2-4-6-5-3-1/h1-4H,5-6H2 |
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|EINECS = 209-764-1 |
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| RTECS = GU4702350 |
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| ChEBI = 37610 |
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|Gmelin = 1657 |
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|Beilstein = 506024 |
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}} |
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|UNNumber = 1993 |
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| Section2 = {{Chembox Properties |
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|SMILES = C\1=C\C=C/CC/1 |
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| Formula = C<sub>6</sub>H<sub>8</sub> |
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|InChI = 1/C6H8/c1-2-4-6-5-3-1/h1-4H,5-6H2 |
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| MolarMass = 80.13 g/mol |
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|RTECS = GU4702350 |
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| Appearance = Colourless liquid |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| Density = 0.841 g/cm³ |
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|ChEBI = 37610 |
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| MeltingPtC = −98 |
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| BoilingPtC = 80 |
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| Solubility = |
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}} |
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| Section7 = {{Chembox Hazards |
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| EUClass = Flammable ('''F''') |
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| MainHazards = |
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| RPhrases = {{R11}} |
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| SPhrases = {{S9}} {{S16}} {{S29}} {{S33}} |
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| FlashPt = 26 °C c.c. |
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| Autoignition = |
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| Section2 = {{Chembox Properties |
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|Formula = C<sub>6</sub>H<sub>8</sub> |
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|MolarMass = 80.13 g/mol |
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|Appearance = Colorless liquid |
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|Density = 0.841 g/cm<sup>3</sup> |
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|MeltingPtC = −98 |
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|BoilingPtC = 80 |
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|MagSus = -48.6·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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| Section3 = {{Chembox Hazards |
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|GHSPictograms = {{GHS02}}{{GHS07}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|225|335}} |
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|PPhrases = {{P-phrases|210|233|240|241|242|243|261|271|280|303+361+353|304+340|312|370+378|403+233|403+235|405|501}} |
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|FlashPtC = 26 |
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|FlashPt_notes = c.c. |
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'''Cyclohexa-1,3-diene''' is an ] with the formula (C<sub>2</sub>H<sub>4</sub>)(CH)<sub>4</sub>. It is a colorless, flammable liquid. Its refractive index is 1.475 (20 °C, D). It is one of two isomers of ], the other being ]. |
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==Synthesis== |
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Cyclohexadiene is prepared by the double ] of 1,2-dibromocyclohexane:<ref>{{cite journal|first1=John P.|last1=Schaefer|first2=Leland |last2=Endres|year=1967|title=1,3-Cyclohexadiene|page=31|journal=Organic Syntheses|volume=47|doi=10.15227/orgsyn.047.0031}}</ref> |
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:(CH<sub>2</sub>)<sub>4</sub>(CHBr)<sub>2</sub> + 2 NaH → (CH<sub>2</sub>)<sub>2</sub>(CH)<sub>4</sub> + 2 NaBr + 2 H<sub>2</sub> |
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==Reactions== |
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Useful reactions of this diene are ]s, such as the ].<ref>Sanjeeva Rao Guppi, George A. O'Doherty, "1,3-Cyclohexadiene" Encyclopedia of Reagents for Organic Synthesis, 2008 John Wiley & Sons. {{doi|10.1002/047084289X.rn00921}}</ref> |
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Conversion of cyclohexa-1,3-diene to benzene + hydrogen is exothermic by about 25 kJ/mol in the gas phase.<ref>US National Institute of Standards and Technology, NIST Chemistry WebBook </ref><ref>J. Sherman {{Webarchive|url=https://web.archive.org/web/20110714081315/http://resources.metapress.com/pdf-preview.axd?code=xg78062p2312q56g&size=largest |date=2011-07-14}} Journal of the American Oil Chemists' Society; Volume 16, Number 2 / February, 1939</ref> |
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:cyclohexane → cyclohexa-1,3-diene + 2 H<sub>2</sub> (Δ''H'' = +231.5 kJ/mol; endothermic) |
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:cyclohexane → benzene + 3 H<sub>2</sub> (Δ''H'' = +205 kJ/mol; endothermic) |
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:cyclohexa-1,3-diene → benzene + H<sub>2</sub> (Δ''H'' = -26.5 kJ/mol; exothermic) |
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Compared with its ] ], cyclohexa-1,3-diene is about 1.6 kJ/mol more stable.<ref>NIST Chemistry WebBook </ref> |
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Cyclohexadiene and its derivatives form ] complexes. Illustrative is , an orange liquid. This complex reacts with hydride-abstracting reagents to give the cyclohexadienyl derivative <sup>+</sup>.<ref>{{cite journal|title=Cyclohexadieneiron Tricarbonyl|first1=Anthony J.|last1=Pearson|first2=Huikai|last2=Sun|year=2008|doi=10.1002/047084289X.rn00791 |
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|journal=E-EROS Encyclopedia of Reagents for Organic Synthesis|isbn=978-0471936237 }}</ref> Cyclohexadienes react with ] to give ].<ref>{{cite book|last1=Bennett|first1=M. A.|last2=Huang|first2=T. N.|last3=Matheson|first3=T. W.|last4=Smith|first4=A. K.|title=(η{{sup|6}}-Hexamethylbenzene)ruthenium Complexes|chapter=16. (η6 -Hexamethylbenzene)Ruthenium Complexes |series=Inorganic Syntheses|year=1982|volume=21|pages=74–78|doi=10.1002/9780470132524.ch16|isbn=9780470132524 }}</ref> |
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==Occurrence== |
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Cyclohexa-1,3-diene itself is rare in nature, but the cyclohexa-1,3-diene motif is fairly common.<ref>{{cite book |doi=10.1016/B978-044453347-0.50066-5 |chapter=Natural Products Containing a Cyclohexane, Cyclohexene, or Cyclohexadiene Subunit |title=Second Supplements to the 2nd Edition of Rodd's Chemistry of Carbon Compounds |date=1991 |last1=Gribble |first1=G.W. |pages=375–445 |isbn=978-0-444-53347-0 }}</ref> One example is ], an intermediate in the ]. Of the several examples of the ]s and ]s, a prominent example is ]. An unusual derivative is ]. |
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]-conjugated to the 2-position of cyclohexadiene-2-carboxylic acid is an intermediate in the biodegradation of aromatic carboxylic acids.<ref name= Porter>{{cite journal |pmid=24767428 |date=2014 |last1=Porter |first1=A. W. |last2=Young |first2=L. Y. |title=Benzoyl-CoA, a Universal Biomarker for Anaerobic Degradation of Aromatic Compounds |journal=Advances in Applied Microbiology |volume=88 |pages=167–203 |doi=10.1016/B978-0-12-800260-5.00005-X |isbn=978-0-12-800260-5 }}</ref> |
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==See also== |
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* ] |
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* ] |
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==References== |
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{{reflist}} |
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{{Cycloalkenes}} |
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{{DEFAULTSORT:Cyclohexadiene, 1, 3-}} |
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] |
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] |