Dimethyl sulfoxide

"DMSO" redirects here. For other uses, see DMSO (disambiguation).
Dimethyl sulfoxide
Stereo structural formula of dimethyl sulfoxide with an explicit electron pair and assorted dimensions
Stereo structural formula of dimethyl sulfoxide with an explicit electron pair and assorted dimensions
Spacefill model of dimethyl sulfoxide
Spacefill model of 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[1]
Identifiers
3D model (JSmol)
Abbreviations DMSO, Me2SO
506008
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.604 Edit this at Wikidata
EC Number
  • 200-664-3
1556
KEGG
MeSH Dimethyl+sulfoxide
RTECS number
  • PV6210000
UNII
  • InChI=1S/C2H6OS/c1-4(2)3/h1-2H3 checkY
    Key: IAZDPXIOMUYVGZ-UHFFFAOYSA-N checkY
  • InChI=1/C2H6OS/c1-4(2)3/h1-2H3
    Key: IAZDPXIOMUYVGZ-UHFFFAOYAR
  • CS(=O)C
  • CS(C)=O
Properties
C2H6OS
Molar mass 78.13 g·mol−1
Appearance Colourless liquid
Density 1.1004 g⋅cm−3
Melting point 19 °C (66 °F; 292 K)
Boiling point 189 °C (372 °F; 462 K)
Miscible
Solubility in Diethyl ether Not soluble
Vapor pressure 0.556 millibars or 0.0556 kPa at 20 °C[2]
Acidity (pKa) 35[3]
1.479
εr = 48
Viscosity 1.996 cP at 20 °C
Structure
Cs
Trigonal pyramidal
3.96 D
Pharmacology
G04BX13 (WHO) M02AX03 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Flash point 89 °C (192 °F; 362 K)
Safety data sheet (SDS) Oxford MSDS
Related 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).
checkY verify (what is checkY☒N ?)

Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula (CH3)2SO. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic 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 skin.[5]

In terms of chemical structure, the molecule has idealized Cs symmetry. It has a trigonal pyramidal molecular geometry consistent with other three-coordinate S(IV) compounds,[6] with a nonbonded electron pair on the approximately tetrahedral sulfur atom.

  1. ^ DMSO (medication)
  2. ^ "Dimethyl Sulfoxide (DMSO) -- Technical". Atofina Chemicals, inc. Retrieved 26 May 2007.
  3. ^ Matthews WS, Bares JE, Bartmess JE, Bordwell FG, Cornforth FJ, Drucker GE, Margolin Z, McCallum RJ, McCollum GJ, Vanier NR (1975). "Equilibrium acidities of carbon acids. VI. Establishment of an absolute scale of acidities in dimethyl sulfoxide solution". J. Am. Chem. Soc. 97 (24): 7006–7014. doi:10.1021/ja00857a010.
  4. ^ "Dimethyl sulfoxide". pubchem.ncbi.nlm.nih.gov.
  5. ^ Novak KM, ed. (2002). Drug Facts and Comparisons (56th ed.). St. Louis, Missouri: Wolters Kluwer Health. p. 2345. ISBN 978-1-57439-110-7.
  6. ^ Thomas R, Shoemaker CB, Eriks K (1966). "The Molecular and Crystal Structure of Dimethyl Sulfoxide, (H3C)2SO". Acta Crystallogr. 21 (1): 12–20. Bibcode:1966AcCry..21...12T. doi:10.1107/S0365110X66002263.