Deuterated DMSO

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 ‹See TfM›N
3D model (JSmol)	Interactive image
Abbreviations	DMSO-d6
Beilstein Reference	1237248
ChemSpider	67699 (anhydrate) Y
ECHA InfoCard	100.016.925
EC Number	218-617-0
PubChem CID	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).
‹See TfM›N verify (what is Y‹See TfM›N ?)
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. However commercially available samples are not 100% pure and a residual DMSO-d₆¹H NMR signal is observed at 2.50ppm (quintet, J_HD=1.9Hz). The ¹³C chemical shift of DMSO-d₆ is 39.52ppm (septet).^[2]

References

1. 
   ^ Fruhstorfer, Wolfgang; Hampel, Bruno, (E. Merck A.-G.); 1964; "Hexadeuterodimethyl sulfoxide."; DE 1171422 (B)
   


2. 
   ^ Hugo E. Gottlieb, Vadim Kotlyar, Abraham Nudelman, "NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities", J. Org. Chem., 1997, 62, 7512-7515 doi:10.1021/jo971176v
   

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

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