Dimethyl sulfite

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Dimethyl sulfite
Dimethyl-sulfite-2D-semi-structural-formula.png
Dimethyl-sulfite-GG-conformer-Spartan-MP2-3D-balls.png
Names
IUPAC name
Methoxysulfinyloxymethane
Other names
Dimethyl sulphite
Sulfurous acid, dimethyl ester
DMSO3[1]
Identifiers
616-42-2 YesY
ChEBI CHEBI:48858 YesY
ChemSpider 62436 YesY
EC number 210-481-0
Jmol-3D images Image
Image
PubChem 69223
Properties
C2H6O3S
Molar mass 110.13 g·mol−1
Appearance Clear liquid
Density 1.29 g/cm3
Boiling point 126 °C (259 °F; 399 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Dimethyl sulfite is a sulfite ester with the chemical formula (CH3O)2SO.

Dimethyl sulfite is used as an additive in some polymers to prevent oxidation.[2] It is also a potentially useful high energy battery electrolyte solvent.[3]

Structure and conformation[edit]

The dimethyl sulfite molecule can adopt several conformations. The most stable is the GG conformer.[1] Each C–O bond is gauche to the S=O bond, depicted below.

Structural formula of the GG conformation of dimethyl sulfite

Preparation[edit]

Although formally derived from sulfurous acid, dimethyl sulfite is prepared from thionyl chloride and methanol.

OSCl2 + 2CH3OH → OS(OCH3)2 + 2HCl

See also[edit]

References[edit]

  1. ^ a b Borba, A.; Gómez-Zavaglia, A.; Simões, P. N. N. L.; Fausto, R. (2005). "Matrix Isolation FTIR Spectroscopic and Theoretical Study of Dimethyl Sulfite". J. Phys. Chem. A 109 (16): 3578–3586. doi:10.1021/jp050020t. 
  2. ^ Guenther, A.; Koenig, T.; Habicher, W. D.; Schwetlick, K. (1997). "Antioxidant action of organic sulfites. I. Esters of sulfurous acid as secondary antioxidants". Polymer Degradation and Stability 55 (2): 209–216. doi:10.1016/S0141-3910(96)00150-4. 
  3. ^ N. P. Yao, E. D'Orsay, and D. N. Bennion (1968). "Behavior of Dimethyl Sulfite as a Potential Nonaqueous Battery Solvent". J. Electrochem. Soc. 115 (10): 999–1003. doi:10.1149/1.2410917. 

External links[edit]