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Unfortunately, it is a relatively weak methylating agent compared to these traditional reagents.
MeSO is mainly used as a methylating agent in organic synthesis.
The rate of reaction is even faster with stronger methylating agents, such as methyl trifluoromethanesulfonate.
For example, S-adenosylmethionine acts as a methylating agent in biological S2 reactions.
Dimethyl carbonate is a mild methylating agent as well.
Compared to other methylating agents, dimethyl sulfate is preferred by the industry because of its low cost and high reactivity.
Methylating agents attack the amine to give the quaternary ammonium salt:
In general, the toxicity of methylating agents is correlated with their efficiency as methyl transfer reagents.
It is a potent carcinogen that acts as a DNA methylating agent.
Milder methylating agents include tetramethyltin, dimethylzinc, and trimethylaluminium.
The compound is a popular methylating agent in the laboratory, but it is too hazardous to be employed on an industrial scale without special precautions.
Demethylation (the transfer of the methyl group to another compound) is a common process, and reagents that undergo this reaction are called methylating agents.
These compounds alkylate faster and with wider range of substrates than traditional methylating agents such as methyl iodide.
Induction of sister chromatid exchange in multiple murine tissues in vivo by various methylating agents.
Common methylating agents are dimethyl sulfate, methyl iodide, and methyl triflate.
Trimethyl phosphate is a mild methylating agent, useful for dimethylation of anilines and related heterocyclic compounds.
Four genes have been identified that contribute to the adaptive response against methylating agents: ada, alkA, alkB and aidB.
Unexpectedly, methyl methanesulphonate, a DNA methylating agent and mutagen, was a potent inducer of catalase (8 fold).
Bromomethane is also a precursor in the manufacture of other chemicals as a methylating agent, and has been used as a solvent to extract oil from seeds and wool.
The largest use of dimethyl ether is as the feedstock for the production of the methylating agent, dimethyl sulfate, which entails its reaction with sulfur trioxide:
Trimethyloxonium tetrafluoroborate MeOBF (sometimes called the "Meerwein salt" after Hans Meerwein) is a strong methylating agent.
Ethylene carbonate (and propylene carbonate) may be converted to dimethyl carbonate (a useful solvent and a mild methylating agent) via transesterification by methanol:
Strongly nucleophilic methylating agents include methyllithium (CHLi) or Grignard reagents methylmagnesium bromide (CHMgX).
It may be produced by accident when methamphetamine is synthesised by methylation of amphetamine if the reaction temperature is too high or an excess of methylating agent is used.
This compound has found use as a methylating agent and more recently as a solvent that is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the US.