| Revision as of 13:39, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 472194609 of page Deuterated_DMSO for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 15:40, 3 May 2024 edit Xiongu (talk | contribs)443 edits Source info. |
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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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| verifiedrevid = 443585497 |
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| Watchedfields = changed |
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| ImageFile = Deuterated DMSO.svg |
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| verifiedrevid = 477002518 |
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| ImageSize = 200px |
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| ImageName = Wireframe of deuterated DMSO |
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| ImageFile = DMSO deuterated structure.png |
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| ImageSize = |
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| PIN = Trideuterio(trideuteriomethylsulfinyl)methane |
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| ImageName = Wireframe of deuterated DMSO |
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| SystematicName = (<sup>2</sup>''H''<sub>3</sub>)Methanesulfinyl(<sup>2</sup>''H''<sub>3</sub>)methane |
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| ImageFile2 = DMSO-d6.jpg |
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| OtherNames = Deuterated dimethyl sulfoxide |
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| PIN = (<sup>2</sup>H<sub>3</sub>)methane |
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|Section1= {{Chembox Identifiers |
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| Abbreviations = DMSO-d6 |
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| OtherNames = Deuterated dimethyl sulfoxide, DMSO-d6 |
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|Section1={{Chembox Identifiers |
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| InChI1 = 1/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3 |
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| Abbreviations = DMSO-d6 |
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| InChI1 = 1/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3 |
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| InChIKey1 = IAZDPXIOMUYVGZ-WFGJKAKNEE |
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| InChIKey1 = IAZDPXIOMUYVGZ-WFGJKAKNEE |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 2206-27-1 --> |
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| CASNo = 2206-27-1 |
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| PubChem = 75151 |
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| PubChem = 75151 |
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| PubChem_Comment = (anhydrate) |
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| PubChem_Comment = (anhydrate) |
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| ChemSpiderID = 67699 |
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| PubChem_Ref = {{Pubchemcite}} |
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| ChemSpiderID_Comment = (anhydrate) |
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| ChemSpiderID = 67699 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Comment = (anhydrate) |
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| EINECS = 218-617-0 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| EINECS = 218-617-0 |
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| RTECS = PV6210000 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| RTECS = PV6210000 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3 |
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| StdInChI = 1S/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = IAZDPXIOMUYVGZ-WFGJKAKNSA-N |
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| StdInChIKey = IAZDPXIOMUYVGZ-WFGJKAKNSA-N |
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| SMILES = C()()S(=O)C()() |
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| SMILES = C()()S(=O)C()() |
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| InChI = 1S/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3 |
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| InChI = 1S/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3 |
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| InChIKey = IAZDPXIOMUYVGZ-WFGJKAKNSA-N |
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| InChIKey = IAZDPXIOMUYVGZ-WFGJKAKNSA-N |
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| Beilstein = 1237248}} |
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| Beilstein = 1237248}} |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>2</sub>D<sub>6</sub>OS |
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| Formula = C<sub>2</sub>D<sub>6</sub>OS |
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| MolarMass = 84.17 g/mol |
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| MolarMass = 84.17 g/mol |
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| ExactMass = 84.051596 u |
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| Appearance = |
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| Appearance = |
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| Density = |
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| Density = 1.19 g/cm<sup>3</sup> (20 °C) |
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| MeltingPtC = 20.2 |
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| MeltingPt = <!-- °C --> |
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| BoilingPt = <!-- °C --> |
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'''Deuterated DMSO''', also known as '''dimethyl sulfoxide-d<sub>6</sub>''', is an ] of ] (DMSO, (CH<sub>3</sub>)<sub>2</sub>S=O)) with chemical formula ((CD<sub>3</sub>)<sub>2</sub>S=O) in which the ] atoms ("H") are replaced with their ] ] ("D"). Deuterated DMSO is a common ] used in ]. |
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==Production== |
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Deuterated DMSO is produced by heating DMSO in ] (D<sub>2</sub>O) with a basic catalyst such as ]. The reaction does not give complete conversion to the d<sub>6</sub> product, and the ] produced must be removed and replaced with D<sub>2</sub>O several times to drive the ] to the fully deuterated product.<ref>{{cite patent |country= DE|number= 1171422B|status= application|title= Process for the production of hexadeuterodimethyl sulfoxide|pubdate= 1964-06-04|fdate= 1962-10-25|pridate= 1962-10-25|invent1= Fruhstorfer, Wolfgang|invent2= Hampel, Bruno|assign1= E. Merck A.G.}}</ref> |
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==Use in NMR spectroscopy== |
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Pure deuterated DMSO shows no peaks in <sup>1</sup>H ] and as a result is commonly used as an NMR solvent.<ref>{{Cite journal |last=Chandak |first=MS |last2=Nakamura |first2=T |last3=Takenaka |first3=T |last4=Chaudhuri |first4=TK |last5=Yagi-Utsumi |first5=M |last6=Chen |first6=J |last7=Kuwajima |first7=K |date=22 January 2013 |title=The use of spin desalting columns in DMSO-quenched H/D-exchange NMR experiments |url=https://onlinelibrary.wiley.com/doi/10.1002/pro.2221 |journal=] |language=en |location=Hoboken, New Jersey, USA |publisher=] |volume=22 |issue=4 |pages=486–91 |doi=10.1002/pro.2221 |pmc=3610054 |pmid=23339068 |url-access=subscription |access-date=2 June 2023}}</ref> However commercially available samples are not 100% pure and a residual DMSO-d<sub>5</sub> <sup>1</sup>H NMR signal is observed at 2.50ppm (quintet, J<sub>HD</sub>=1.9Hz). The <sup>13</sup>C chemical shift of DMSO-d<sub>6</sub> is 39.52ppm (septet).<ref>{{Cite journal |last=Gottlieb |first=Hugo E. |last2=Kotlyar |first2=Vadim |last3=Nudelman |first3=Abraham |date=17 October 1997 |title=NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities |url=https://pubs.acs.org/doi/full/10.1021/jo971176v |journal=] |language=en |location=Washington, D.C., USA |publisher=] |volume=62 |issue=21 |pages=7512–7515 |doi=10.1021/jo971176v |pmid=11671879 |url-access=subscription |access-date=18 June 2011}}</ref> |
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==References== |
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{{reflist}} |
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{{List of NMR solvents}} |
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] |