Deuterated DMSO

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

Wireframe of 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.^[1]

Applications

NMR spectroscopy

¹³C NMR Spectrum of DMSO-d₆

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.^[2] 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 (J_HD=1.9Hz). In ¹³C-NMR, the chemical shift of DMSO-d₆ is 39.52 ppm, and appears as a septet.^[3]

Trideuteromethyl donor

Deuterated DMSO is used as a reagent for the introduction of a trideuteromethyl group (CD₃) onto organic structures.^[4]