Dimetyylisulfaatin

Dimetyylisulfaatin, known in English as dimethyl sulfate (DMS), is an organosulfur compound with the chemical formula C₂H₆O₄S. It is a clear, colorless to yellowish liquid that evaporates quickly and has a sweet, menthol‑like odor. DMS is a highly reactive alkylating agent and one of the most potent, ominously capable of transferring a methylene group to a wide range of nucleophiles, including amines, alcohols, carboxylates and thiols. Its electrophilic center is the sulfur atom bonded to two methoxy groups, which can be hydrolysed to produce methanesulfonic acid and methanol in the presence of nucleophiles.

The compound has been used extensively in laboratory and industrial settings. In organic synthesis it serves as a methylating reagent for the preparation of methyl esters, ethers, amides and numerous alkylated aromatics. In the pharmaceutical industry it enables late‑stage methylation steps that are difficult to achieve by other reagents. DMS is also employed in the vapor phase as a fumigant for pest control and works as an explosive ingredient in high‑energy propellants because of its high propellant value and oxygen content.

Handling dimetyylisulfaatin requires stringent safety measures. It is acutely toxic if swallowed or absorbed through the skin and can cause severe irritation of the eyes and respiratory tract. Inhalation of vapour or dust can lead to systemic toxicity, including kidney and liver damage. Laboratories that use DMS must employ proper ventilation, personal protective equipment, and containment systems, and waste must be neutralised with aqueous base before disposal.

In addition to synthetic applications, dimetyylisulfaatin has been investigated as a reagent for DNA alkylation studies, for developing new covalent organometallic catalysts, and for environmental remediation processes such as the methylation of organophosphate pesticides. Its high reactivity also underpins several therapeutic strategies where controlled alkylation of biological molecules is required.