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Topic summary

Dimethyl sulfoxide

Dimethyl sulfoxide
A sample of dimethyl sulfoxide
Names Preferred IUPAC name
(Methanesulfinyl)methane
Systematic IUPAC name
(Methanesulfinyl)methane (substitutive)
Dimethyl(oxido)sulfur (additive)
Other names
Methylsulfinylmethane
Methyl sulfoxide (2:1), Dermasorb
Identifiers
3D model (JSmol)
Abbreviations DMSO, Me2SO 506008 ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.000.604EC Number
  • 200-664-3
1556 KEGG
MeSHDimethyl+sulfoxide
RTECS number
  • PV6210000
UNII
  • InChI=1S/C2H6OS/c1-4(2)3/h1-2H3
    Key: IAZDPXIOMUYVGZ-UHFFFAOYSA-N
  • InChI=1/C2H6OS/c1-4(2)3/h1-2H3
    Key: IAZDPXIOMUYVGZ-UHFFFAOYAR
  • CS(=O)C
  • CS(C)=O
Properties C2H6OSMolar mass78.13 g·mol Appearance Colourless liquid Density1.1004g⋅cm Melting point19 °C (66 °F; 292 K) Boiling point189 °C (372 °F; 462 K) Miscible Solubility in Diethyl etherNot soluble Vapor pressure0.556 millibars or 0.0556 kPa at 20 °C Acidity (pKa) 35 1.479
εr = 48 Viscosity1.996cP at 20 °C Structure CsTrigonal pyramidal 3.96DPharmacology G04BX13 (WHO) M02AX03 (WHO) Hazards Occupational safety and health (OHS/OSH):
Main hazards
Irritant NFPA 704 (fire diamond)
1
2
0
Flash point89 °C (192 °F; 362 K) Safety data sheet (SDS) Sigma-Aldrich SDSRelated compounds
Related sulfoxides
Diethyl sulfoxide
Related compounds
Supplementary data page Dimethyl sulfoxide (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula(CH3)2S=O. This colorless liquid is the sulfoxide most widely used commercially. It is an important polaraprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. It has a relatively high boiling point. DMSO is metabolised to compounds that leave a garlic-like taste in the mouth after DMSO is absorbed by the skin.

In terms of chemical structure, the molecule has idealized Cssymmetry. It has a trigonal pyramidal molecular geometry consistent with other three-coordinate S(IV) compounds, with a nonbonded electron pair on the approximately tetrahedral sulfur atom.

Wikipedia source