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Dimethylsulfoxide

Dimethyl sulfoxide
Dimethylsulfoxid.svg
Stereo structural formula of dimethyl sulfoxide with an explicit electron pair and assorted dimensions
Spacefill model of dimethyl sulfoxide
Sample of Dimethyl sulfoxide 01.jpg
A sample of dimethyl sulfoxide
Names
IUPAC name
Dimethyl sulfoxide
Systematic IUPAC name
Methanesulfinylmethane (substitutive)
Dimethyl(oxido)sulfur (additive)
Other names
Methylsulfinylmethane
Methyl sulfoxide
Identifiers
3D model (Jmol)
Abbreviations DMSO, Me2SO
506008
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.000.604
EC Number 200-664-3
1556
KEGG
MeSH Dimethyl+sulfoxide
PubChem CID
RTECS number PV6210000
UNII
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 very soluble
Acidity (pKa) 35
1.479
εr = 48
Viscosity 1.996 cP at 20 °C
Structure
Cs
trigonal pyramidal
3.96 D
Pharmacology
G04BX13 (WHO) M02AX03 (WHO)
Hazards
Main hazards Irritant and flammable
Safety data sheet See: data page
Oxford MSDS
R-phrases R36/37/38
S-phrases S26, S37/39
NFPA 704
Flammability code 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 fuel Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 89 °C
Related compounds
Related sulfoxides
diethyl sulfoxide
Related compounds
sodium methylsulfinylmethylide,
dimethyl sulfide,
dimethyl sulfone,
acetone
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula (CH3)2SO. This colorless liquid 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 melting point. DMSO has the unusual property that many individuals perceive a garlic-like taste in the mouth after contact with the skin.

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, with a nonbonded electron pair on the approximately tetrahedral sulfur atom.

It was first synthesized in 1866 by the Russian scientist Alexander Zaytsev, who reported his findings in 1867. Dimethyl sulfoxide is produced industrially from dimethyl sulfide, a by-product of the Kraft process, by oxidation with oxygen or nitrogen dioxide.

The sulfur center in DMSO is nucleophilic toward soft electrophiles and the oxygen is nucleophilic toward hard electrophiles. With methyl iodide it forms trimethylsulfoxonium iodide, [(CH3)3SO]I:


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