| Revision as of 16:42, 23 May 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_t← Previous edit |
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{{Unreferenced|date = February 2007}} |
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{{Chembox |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 430465662 |
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| verifiedrevid = 430535242 |
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| ImageFileL1 = Deuterated benzene.svg |
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| ImageFileL1 = Deuterated benzene.svg |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageSizeL1 = 121 |
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| ImageNameL1 = Kekulé, skeletal formula of deuterated benzene |
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| ImageNameL1 = Kekulé, skeletal formula of deuterated benzene |
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| ImageFileR1 = Benzene-3D-vdW.png |
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| ImageFileR1 = Benzene-3D-vdW.png |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| ImageSizeR1 = 121 |
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| ImageNameR1 = Spacefill model of deuterated benzene |
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| ImageNameR1 = Spacefill model of deuterated benzene |
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| ImageFile2 = Benzene-aromatic-3D-balls.png |
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| ImageFile2 = Benzene-aromatic-3D-balls.png |
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| ImageSize2 = 121 |
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| ImageSize2 = 121 |
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| ImageName2 = Ball and stick model of deuterated benzene |
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| ImageName2 = Ball and stick model of deuterated benzene |
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| PIN = (<sup>2</sup>H<sub>6</sub>)Benzene<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=1142 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 1076-43-3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 71601 |
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| CASNo = 1076-43-3 |
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| PubChem_Ref = {{Pubchemcite|correct|pubchem}} |
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| ChemSpiderID = 64671 |
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| PubChem = 71601 |
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| ChemSpiderID = 64671 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| EINECS = 214-061-8 |
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| UNNumber = 1114 |
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| ChEBI = 193039 |
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| Beilstein = 1905426 |
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| EINECS = 214-061-8 |
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| UNNumber = 1114 |
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| SMILES = c1c()c()c()c()c1 |
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| Beilstein = 1905426 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| SMILES = c1c()c()c()c()c1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H6/c1-2-4-6-5-3-1/h1-6H/i1D,2D,3D,4D,5D,6D |
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| StdInChI = 1S/C6H6/c1-2-4-6-5-3-1/h1-6H/i1D,2D,3D,4D,5D,6D |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = UHOVQNZJYSORNB-MZWXYZOWSA-N |
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| StdInChIKey = UHOVQNZJYSORNB-MZWXYZOWSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>6</sub><sup>2</sup>H<sub>6</sub> |
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| Formula = C<sub>6</sub><sup>2</sup>H<sub>6</sub> or C<sub>6</sub>D<sub>6</sub> |
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| MolarMass = 84.1488 g mol<sup>−1</sup> |
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| MolarMass = 84.1488 g mol<sup>−1</sup> |
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| ExactMass = 84.084610668 g mol<sup>−1</sup> |
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| Density = 0.950 g cm<sup>−3</sup> |
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| MeltingPtK = 280 |
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| Density = 0.950 g cm<sup>−3</sup> |
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| MeltingPtK = 280 |
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| BoilingPtK = 352 |
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| BoilingPtK = 345 |
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}} |
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| Section3 = {{Chembox Thermochemistry |
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|Section3={{Chembox Thermochemistry |
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| HeatCapacity = 152.46 J K<sup>−1</sup> mol<sup>−1</sup> |
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| HeatCapacity = 152.46 J K<sup>−1</sup> mol<sup>−1</sup> |
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}} |
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| Section4 = {{Chembox Hazards |
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|Section4={{Chembox Hazards |
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| EUClass = {{Hazchem F}} {{Hazchem T}} |
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| GHSPictograms = {{GHS05}}{{GHS07}}{{GHS08}} |
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| GHSSignalWord = Danger |
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| RPhrases = {{R45}}, {{R46}}, {{R11}}, {{R36/38}}, {{R48/23/24/25}}, {{R65}} |
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| HPhrases = {{H-phrases|225|304|315|319|340|350|372}} |
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| SPhrases = {{S53}}, {{S45}} |
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| PPhrases = {{P-phrases|201|202|210|233|240|241|242|243|260|264|270|280|281|301+310|302+352|303+361+353|305+351+338|308+313|314|321|331|332+313|337+313|362|370+378|403+235|405|501}} |
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| NFPA-H = 2 |
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| NFPA-F = 3 |
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| NFPA-H = 2 |
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| NFPA-R = 0 |
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| NFPA-F = 3 |
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| NFPA-R = 0 |
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| FlashPt = −11 °C |
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| FlashPtC = −11 |
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}} |
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}} |
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| Section5 = {{Chembox Related |
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|Section5={{Chembox Related |
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| OtherCpds = ] |
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| OtherCompounds = ] |
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'''Deuterated benzene''' (C<sub>6</sub>D<sub>6</sub>), is a form (called an ]) of ] (C<sub>6</sub>H<sub>6</sub>)in which the ] atom ("H") is replaced with ] (heavy hydrogen) ] ("D"). Deuterated benzene is a common ] used in ]. |
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'''Deuterated benzene''' (C<sub>6</sub>D<sub>6</sub>) is an ] of ] (C<sub>6</sub>H<sub>6</sub>) in which the ] atom ("H") is replaced with ] (heavy hydrogen) ] ("D"). |
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==Properties== |
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The properties of deuterated benzene are very similar to those of normal benzene, however, the increased atomic weight of deuterium relative to protium means that the melting point of C<sub>6</sub>D<sub>6</sub> is about 1.3 °C higher than that of the nondeuterated analogue. The boiling points of both compounds, however, are the same: 80 °C.<ref>{{cite web | website=sigmaaldrich.com|title=Benzene-d6| url=https://www.sigmaaldrich.com/CA/en/product/aldrich/151815?context=product | access-date=4 August 2023}}</ref> |
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==Applications== |
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Deuterated benzene is a common ] used in ]. It is widely used for taking spectra of ], which often react with the cheaper deuterated chloroform.<ref>{{cite journal|doi=10.1021/om100106e|title=NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist|journal=Organometallics|volume=29|issue=9|pages=2176–2179|year=2010|last1=Fulmer|first1=Gregory R.|last2=Miller|first2=Alexander J. M.|last3=Sherden|first3=Nathaniel H.|last4=Gottlieb|first4=Hugo E.|last5=Nudelman|first5=Abraham|last6=Stoltz|first6=Brian M.|last7=Bercaw|first7=John E.|last8=Goldberg|first8=Karen I.|url=https://authors.library.caltech.edu/18475/2/om100106e_si_001.pdf}}</ref> |
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A slightly more exotic application of C<sub>6</sub>D<sub>6</sub> is in the synthesis of molecules containing a deuterated ] group. Deuterated benzene will undergo all the same reactions its normal analogue will, just a little more slowly due to the ]. For example, deuterated benzene could be used in the synthesis of deuterated ], if desired: |
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] |
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Many simple monosubstituted aromatic compounds bearing the deuterated phenyl (C<sub>6</sub>D<sub>5</sub>) group may be purchased commercially, such as ], ], ], ], and more. |
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==References== |
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{{Reflist}} |
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{{List of NMR solvents}} |
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{{List of NMR solvents}} |
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{{DEFAULTSORT:Deuterated Benzene}} |
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{{DEFAULTSORT:Deuterated Benzene}} |
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] |
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] |
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