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Dimethyl sulfoxide : ウィキペディア英語版
Dimethyl sulfoxide

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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,〔R. Thomas, C. B. Shoemaker and K. Eriks "The molecular and crystal structure of dimethyl sulfoxide, (H3C)2SO" Acta Cryst. 1966. vol. 21, pp. 12-20. 〕 with a nonbonded electron pair on the approximately tetrahedral sulfur atom.
==Synthesis and production==
It was first synthesized in 1866 by the Russian scientist Alexander Zaytsev, who reported his findings in 1867.〔A. Saytzeff (1867) ("Ueber die Einwirkung von Saltpetersäure auf Schwefelmethyl und Schwefeläthyl" ) (On the effect of nitric acid on methyl sulfide and ethyl sulfide) ''Annalen der Chemie und Pharmacie'', 144: 148–156; see page 150, where dimethyl sulfoxide is called "Dimethylschwefeloxyd".〕 Dimethyl sulfoxide is produced from dimethyl sulfide, a by-product of kraft pulping. It is industrially produced by oxidation of dimethyl sulfide with oxygen or nitrogen dioxide.〔Kathrin-Maria Roy "Sulfones and Sulfoxides" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2002, Wiley-VCH, Weinheim. 〕

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