Dimethyl sulfite is a sulfite ester with the

chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

(CH₃O)₂SO. Dimethyl sulfite is used as an additive in some polymers to prevent oxidation. It is also a potentially useful high energy battery electrolyte solvent.

Structure and conformation

The dimethyl sulfite molecule can adopt several conformations. The most stable is the ''GG'' conformer. Each C–O bond is gauche to the S=O bond, depicted below. Dimethyl-sulfite-GG-conformer-2D

Preparation

Dimethyl sulfite is prepared from a 1:2 ratio of

thionyl chloride Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately per year bein ...

and methanol. The reaction can be catalyzed by tertiary amine bases and likely proceeds via the chlorosulfinate (MeOS(O)Cl), this intermediate will exist only fleetingly in the presence of methanol and as such its decomposition to

methyl chloride Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula . One of the haloalkanes, it is a colorless, odorless, flammable gas. Methyl chloride is a crucial reagent in industrial ...

and

sulfur dioxide Sulfur dioxide (IUPAC-recommended spelling) or sulphur dioxide (traditional Commonwealth English) is the chemical compound with the formula . It is a toxic gas responsible for the odor of burnt matches. It is released naturally by volcanic activ ...

(via the slower

SNi SNI may refer to: Science and technology * Substitution nucleophilic internal, a chemistry reaction mechanism * Swedish Standard Industrial Classification, a Swedish economic classification system * Server Name Indication, an extension to the ...

mechanism) is not observed to any great extent. :

Methyl methanesulfonate Methyl methanesulfonate (MMS), also known as methyl mesylate, is an alkylating agent and a carcinogen. It is also a suspected reproductive toxicant, and may also be a skin/sense organ toxicant. It is used in cancer treatment.Diethyl sulfite Diethyl sulfite (C4H10O3S) is an ester of sulfurous acid. Among other properties, diethyl sulfite inhibits the growth of mold spores during grain storage. Diethyl sulfite is used as an additive in some polymers to prevent oxidation. See also ...

, a similar sulfite ester *

Dimethyl sulfoxide Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula ( CH3)2. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds a ...

Dimethyl sulfate Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as ( CH3)2 SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent ...

, a sulfate ester

References

{{Reflist

External links

WebBook page for C2H6SO3
Organosulfites Methyl esters