Dimethyl sulfite

Dimethyl sulfite
Names
	IUPAC name Methoxysulfinyloxymethane
	Other names Dimethyl sulphite; Sulfurous acid, dimethyl ester; DMSO3
Identifiers
CAS Number	616-42-2;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:48858 ;
ChemSpider	62436 ;
ECHA InfoCard	100.009.529
EC Number	210-481-0;
PubChem CID	69223;
CompTox Dashboard (EPA)	DTXSID3060665 ;
	InChI InChI=1S/C2H6O3S/c1-4-6(3)5-2/h1-2H3 Key: BDUPRNVPXOHWIL-UHFFFAOYSA-N ; InChI=1/C2H6O3S/c1-4-6(3)5-2/h1-2H3 Key: BDUPRNVPXOHWIL-UHFFFAOYAF;
	SMILES COS(=O)OC; O=S(OC)OC;
Properties
Chemical formula	C2H6O3S
Molar mass	110.088 g/mol
Appearance	Clear liquid
Density	1.29 g/cm3
Boiling point	126 °C (259 °F; 399 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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

References

^ ^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.
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

External links

WebBook page for C2H6SO3

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[Fausto-1] 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[1]

[2]

[3]

Structure and conformation

Preparation

See also

References

External links