Deuterated DMSO

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 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.

References

References

1. "Process for the production of hexadeuterodimethyl sulfoxide".
2. Chandak, MS. (22 January 2013). "The use of spin desalting columns in DMSO-quenched H/D-exchange NMR experiments". [[Wiley-Blackwell]].
3. Gottlieb, Hugo E.. (17 October 1997). "NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities". [[American Chemical Society]].
4. (2021). "The Deuterated "Magic Methyl" Group: A Guide to Site-Selective Trideuteromethyl Incorporation and Labeling by Using CD₃ Reagents". Chemistry – A European Journal.