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Deuterated DMSO

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Deuterated DMSO
Wireframe of deuterated DMSO
Names
Preferred IUPAC name (H3)methane
Other names Deuterated dimethyl sulfoxide, DMSO-d6
Identifiers
CAS Number
3D model (JSmol)
Abbreviations DMSO-d6
Beilstein Reference 1237248
ChemSpider
ECHA InfoCard 100.016.925 Edit this at Wikidata
EC Number
  • 218-617-0
PubChem CID
RTECS number
  • PV6210000
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3Key: IAZDPXIOMUYVGZ-WFGJKAKNSA-N
  • InChI=1S/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3Key: IAZDPXIOMUYVGZ-WFGJKAKNSA-N
  • InChI=1/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3Key: IAZDPXIOMUYVGZ-WFGJKAKNEE
SMILES
  • C()()S(=O)C()()
Properties
Chemical formula C2D6OS
Molar mass 84.17 g/mol
Density 1.19 g/cm (20 °C)
Melting point 20.2 °C (68.4 °F; 293.3 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Deuterated DMSO, also known as dimethyl sulfoxide-d6, is an isotopologue of dimethyl sulfoxide (DMSO, (CH3)2S=O)) with chemical formula ((CD3)2S=O) in which the hydrogen atoms ("H") are replaced with their isotope deuterium ("D"). Deuterated DMSO is a common solvent used in NMR spectroscopy.

Production

Deuterated DMSO is produced by heating DMSO in heavy water (D2O) with a basic catalyst such as calcium oxide. The reaction does not give complete conversion to the d6 product, and the water produced must be removed and replaced with D2O several times to drive the equilibrium to the fully deuterated product.

Use in NMR spectroscopy

C NMR Spectrum of DMSO-d6

Pure deuterated DMSO shows no peaks in H NMR spectroscopy and as a result is commonly used as an NMR solvent. However commercially available samples are not 100% pure and a residual DMSO-d5 H NMR signal is observed at 2.50ppm (quintet, JHD=1.9Hz). The C chemical shift of DMSO-d6 is 39.52ppm (septet).

References

  1. DE application 1171422B, Fruhstorfer, Wolfgang & Hampel, Bruno, "Process for the production of hexadeuterodimethyl sulfoxide", published 1964-06-04, assigned to E. Merck A.G. 
  2. Chandak, MS; Nakamura, T; Takenaka, T; Chaudhuri, TK; Yagi-Utsumi, M; Chen, J; Kuwajima, K (22 January 2013). "The use of spin desalting columns in DMSO-quenched H/D-exchange NMR experiments". Protein Sci. 22 (4). Hoboken, New Jersey, USA: Wiley-Blackwell: 486–91. doi:10.1002/pro.2221. PMC 3610054. PMID 23339068. Retrieved 2 June 2023.
  3. Gottlieb, Hugo E.; Kotlyar, Vadim; Nudelman, Abraham (17 October 1997). "NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities". The Journal of Organic Chemistry. 62 (21). Washington, D.C., USA: American Chemical Society: 7512–7515. doi:10.1021/jo971176v. PMID 11671879. Retrieved 18 June 2011.
Deuterated NMR solvents
Reference
1H and 13C chemical shifts
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