Deuterated DMSO

Deuterated DMSO
Names
	Preferred IUPAC name [(2H3)Methanesulfinyl](2H3)methane
	Other names Deuterated dimethyl sulfoxide, DMSO-d6
Identifiers
CAS Number	2206-27-1 ;
3D model (JSmol)	Interactive image;
Abbreviations	DMSO-d6
Beilstein Reference	1237248
ChemSpider	67699 (anhydrate) ;
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 Key: IAZDPXIOMUYVGZ-WFGJKAKNSA-N ; 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). verify (what is ?) 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.^[1]

Use in NMR spectroscopy

Pure deuterated DMSO shows no peaks in ¹H NMR spectroscopy and as a result is commonly used as an NMR solvent.^[2] 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へるつ). The ¹³C chemical shift of DMSO-d₆ is 39.52ppm (septet).^[3]

References

^ DE application 1171422B, Fruhstorfer, Wolfgang & Hampel, Bruno, "Process for the production of hexadeuterodimethyl sulfoxide", published 1964-06-04, assigned to E. Merck A.G.
^ 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. Retrieved 2 June 2023.
^ 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. Retrieved 18 June 2011.

[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. Retrieved 2 June 2023.

[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. Retrieved 18 June 2011.

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v t e Deuterated NMR solvents
Deuterated acetone - (CD₃)₂C=O Deuterated benzene - C₆D₆ Deuterated chloroform - CDCl₃ Deuterated dichloromethane - CD₂Cl₂ Deuterated DMF - (CD₃)₂NCOD Deuterated DMSO - (CD₃)₂S=O Deuterated ethanol - C₂D₅OD Deuterated methanol - CD₃OD Deuterated THF - (C₄D₈)O Deuterated water - D₂O
Reference 1H and 13C chemical shifts