Deuterated DMSO

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Deuterated DMSO
Wireframe of deuterated DMSO
Wireframe of deuterated DMSO
Names
Preferred IUPAC name
[(2H3)Methanesulfinyl](2H3)methane
Other names
Deuterated dimethyl sulfoxide, DMSO-d6
Identifiers
3D model (JSmol)
Abbreviations DMSO-d6
1237248
ChemSpider
ECHA InfoCard 100.016.925 Edit this at Wikidata
EC Number
  • 218-617-0
RTECS number
  • PV6210000
  • InChI=1S/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3 checkY
    Key: IAZDPXIOMUYVGZ-WFGJKAKNSA-N checkY
  • 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
  • [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H]
Properties
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).
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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).

Production

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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

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NMR spectroscopy

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

Trideuteromethyl donor

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

References

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  1. ^ DE application 1171422B, Fruhstorfer, Wolfgang & Hampel, Bruno, "Process for the production of hexadeuterodimethyl sulfoxide", published 1964-06-04, assigned to E. Merck A.G. 
  2. ^ Chandak, MS; Nakamura, T; Takenaka, T; Chaudhuri, TK; Yagi-Utsumi, M; Chen, J; Kuwajima, K (22 January 2013). "The use of spin desalting columns in DMSO-quenched H/D-exchange NMR experiments". Protein Sci. 22 (4). Hoboken, New Jersey, USA: Wiley-Blackwell: 486–91. doi:10.1002/pro.2221. PMC 3610054. PMID 23339068.
  3. ^ Gottlieb, Hugo E.; Kotlyar, Vadim; Nudelman, Abraham (17 October 1997). "NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities". The Journal of Organic Chemistry. 62 (21). Washington, D.C., USA: American Chemical Society: 7512–7515. doi:10.1021/jo971176v. PMID 11671879.
  4. ^ Steverlynck, Joost; Sitdikov, Ruzal; Rueping, Magnus (2021). "The Deuterated "Magic Methyl" Group: A Guide to Site-Selective Trideuteromethyl Incorporation and Labeling by Using CD3 Reagents". Chemistry – A European Journal. 27 (46): 11751–11772. doi:10.1002/chem.202101179. PMC 8457246. PMID 34076925.