Deuterated DMSO

Deuterated DMSO
Identifiers
Abbreviations DMSO-d6
CAS number 2206-27-1 Y
PubChem 75151 (anhydrate) Y
ChemSpider 67699 (anhydrate) Y
EC number 218-617-0
RTECS number PV6210000
Beilstein Reference 1237248
Jmol-3D images Image 1
Properties
Molecular formula C2D6OS
Molar mass 84.17 g/mol
Exact mass 84.051596 u
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.[1]

Use in NMR Spectroscopy

Pure deuterated DMSO shows no peaks in 1H NMR spectroscopy so is commonly used as an NMR solvent. However commercially available samples are not 100% pure and a DMSO quintet peak will be observed in the regions 2.54ppm for 1H NMR and 40.45ppm in 13C NMR.[2]

References

  1. ^ Fruhstorfer, Wolfgang; Hampel, Bruno, (E. Merck A.-G.); 1964; "Hexadeuterodimethyl sulfoxide."; DE 1171422 (B)
  2. ^ Hugo E. Gottlieb, Vadim Kotlyar, Abraham Nudelman, "NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities", J. Org. Chem., 1997, 62, 7512-7515