Deuterated DMSO

Deuterated DMSO
Preferred IUPAC name Trideuterio(trideuteriomethylsulfinyl)methane
Systematic name (2H3)Methanesulfinyl(2H3)methane
Other names Deuterated dimethyl sulfoxide
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
SMILES [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H]
InChI InChI=1S/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3 Y Key: IAZDPXIOMUYVGZ-WFGJKAKNSA-N Y InChI=1S/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3 Key: IAZDPXIOMUYVGZ-WFGJKAKNSA-N InChI=1/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3 Key: IAZDPXIOMUYVGZ-WFGJKAKNEE
Properties
Molecular formula	C2D6OS
Molar mass	84.17 g/mol
Exact mass	84.051596 u
Y DMSO (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Deuterated DMSO, also knows 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

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