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) ;
EC Number	218-617-0;
PubChem CID	75151 (anhydrate);
RTECS number	PV6210000;
	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)
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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	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 deuterium ("D") isotope. Deuterated DMSO is a common solvent used in nuclear magnetic resonance spectroscopy (NMR).

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

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]

References

↑ & Hampel, Bruno"Process for the production of hexadeuterodimethyl sulfoxide" DE patent application 1171422B, 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" (in en). Protein Sci (Hoboken, New Jersey, USA: Wiley-Blackwell) 22 (4): 486–91. doi:10.1002/pro.2221. PMID 23339068.
↑ Gottlieb, Hugo E.; Kotlyar, Vadim; Nudelman, Abraham (17 October 1997). "NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities" (in en). The Journal of Organic Chemistry (Washington, D.C., USA: American Chemical Society) 62 (21): 7512–7515. doi:10.1021/jo971176v. PMID 11671879.
↑ 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. PMID 34076925.

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[1] & Hampel, Bruno"Process for the production of hexadeuterodimethyl sulfoxide" DE patent application 1171422B, 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" (in en). Protein Sci (Hoboken, New Jersey, USA: Wiley-Blackwell) 22 (4): 486–91. doi:10.1002/pro.2221. PMID 23339068.

[3] Gottlieb, Hugo E.; Kotlyar, Vadim; Nudelman, Abraham (17 October 1997). "NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities" (in en). The Journal of Organic Chemistry (Washington, D.C., USA: American Chemical Society) 62 (21): 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. PMID 34076925.

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v t e Deuterated NMR Solvents
Deuterated	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