Deuterated DMSO

Names
Preferred IUPAC name

[(2H3)Methanesulfinyl](2H3)methane

Other names

Deuterated dimethyl sulfoxide, DMSO-d6

Identifiers

CAS Number

* 2206-27-1 Y

3D model (JSmol)

* Interactive image

Abbreviations  | DMSO-d6

Beilstein Reference

| 1237248
ChemSpider |

* 67699 (anhydrate) Y

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)
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).

N verify (what is YN ?)
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).

## Contents

* 1 Production
* 2 Applications
* 2.1 NMR spectroscopy
* 3 Trideuteromethyl donor
* 4 References

## 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

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

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

## References

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 34076925.3+Reagents&rft.jtitle=Chemistry+–+A+European+Journal&rft.aulast=Steverlynck&rft.aufirst=Joost&rft.au=Steverlynck, Joost&rft.au=Sitdikov, Ruzal&rft.au=Rueping, Magnus&rft.date=2021&rft.volume=27&rft.issue=46&rft.pages=11751–11772&rft_id=info:doi/10.1002/chem.202101179&rft_id=info:pmid/34076925&rfr_id=info:sid/en.wikibooks.org:Chemistry:Deuterated_DMSO">

* 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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