Deuterated DMSO

Deuterated DMSO

Wireframe of deuterated DMSO
Names
Preferred IUPAC name Trideuterio(trideuteriomethylsulfinyl)methane
Systematic IUPAC name (2H3)Methanesulfinyl(2H3)methane
Other names Deuterated dimethyl sulfoxide
Identifiers
CAS Number	2206-27-1 N
Abbreviations	DMSO-d6
Beilstein Reference	1237248
ChemSpider	67699 (anhydrate) Y
EC Number	218-617-0
Jmol 3D model	Interactive image
PubChem	75151 (anhydrate)
RTECS number	PV6210000
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)
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

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

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 residual DMSO-d₅ ¹H NMR signal is observed at 2.50ppm (quintet, J_HD=1.9Hz). The ¹³C chemical shift of DMSO-d₆ is 39.52ppm.