Dimethyl sulfite

Dimethyl sulfite
IUPAC name Methoxysulfinyloxymethane
Other names Dimethyl sulphite Sulfurous acid, dimethyl ester DMSO3[1]
Identifiers
CAS number	616-42-2
PubChem	69223
ChemSpider	62436 Y
EC number	210-481-0
ChEBI	CHEBI:48858 Y
Jmol-3D images	Image 1 Image 2
SMILES COS(=O)OC O=S(OC)OC
InChI InChI=1S/C2H6O3S/c1-4-6(3)5-2/h1-2H3 Y Key: BDUPRNVPXOHWIL-UHFFFAOYSA-N Y InChI=1/C2H6O3S/c1-4-6(3)5-2/h1-2H3 Key: BDUPRNVPXOHWIL-UHFFFAOYAF
Properties
Molecular formula	C2H6O3S
Molar mass	110.088 g/mol
Appearance	Clear liquid
Density	1.29 g/cm3
Boiling point	126 °C, 399 K, 259 °F
Y sulfite (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

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.

Preparation

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

OSCl₂ + 2CH₃OH → OS(OCH₃)₂ + 2HCl

See also

• Methyl methanesulfonate, a chemical with the same molecular formula but different arrangement of atoms
• Diethyl sulfite, a similar sulfite ester
• Dimethyl sulfoxide
• Dimethyl sulfate, a sulfate ester

References

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

• WebBook page for C2H6SO3

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