Deuterated DMSO

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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 deuterium ("D") isotope. Deuterated DMSO is a common solvent used in nuclear magnetic resonance spectroscopy (NMR).

Deuterated DMSO
Names
Preferred IUPAC name
[(2H3)Methanesulfinyl](2H3)methane
Other names
Deuterated dimethyl sulfoxide, DMSO-d6
Identifiers
CAS Number
  • 2206-27-1 Y
3D model (JSmol)
  • Interactive image
Abbreviations DMSO-d6
Beilstein Reference
 1237248
ChemSpider
  • 67699 (anhydrate) Y
ECHA InfoCard 100.016.925
EC Number
  • 218-617-0
PubChem CID
  • 75151 (anhydrate)
RTECS number
  • PV6210000
CompTox Dashboard (EPA)
  • DTXSID90944686
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
SMILES
  • [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H]
Properties
Chemical formula
 C2D6OS
Molar mass 84.17 g/mol
Density 1.19 g/cm3 (20 °C)
Melting point 20.2 °C (68.4 °F; 293.3 K)
Boiling point 189 °C (372 °F; 462 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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.

Applications

NMR spectroscopy

DMSO is a good solvent for many organic compounds. Because deuterated DMSO does not contain any 1</1H atoms, it produces no peaks in 1H-NMR and as a result is commonly used as a solvent for NMR experiments. Commercially available deuteriated DMSO is not isotopically pure. The residual DMSO-d5 produces a 1H-NMR signal observed at 2.50 ppm, which appears as a quintet (JHD=1.9Hz). In 13C-NMR, the chemical shift of DMSO-d6 is 39.52 ppm, and appears as a septet.

Trideuteromethyl donor

Deuterated DMSO is used as a reagent for the introduction of a trideuteromethyl group (CD3) onto organic structures.

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