Iodomethane

Iodomethane, or methyl iodide, is a volatile organoiodine compound with formula CH₃I. It is an alkylating reagent in chemical synthesis and was formerly used as a soil fumigant.

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Nucleophilic substitution: A reaction in which a nucleophile replaces a leaving group attached to an electrophilic atom. Nucleophiles commonly displace iodide from iodomethane in carbon–carbon bond-forming reactions.
Methylation: The addition of a methyl group to a molecule. Iodomethane is used to methylate oxygen, nitrogen, sulfur, and carbon nucleophiles.
Organoiodine compound: An organic compound containing at least one carbon–iodine bond. Iodomethane is the simplest member of this family.
Methyl iodide toxicity: The harmful effects caused by exposure to iodomethane, especially through inhalation or skin contact. Its acute toxicity requires stringent precautions when the compound is handled.
SN2 reaction: A concerted substitution in which a nucleophile attacks as a leaving group departs. Iodomethane is a classic substrate for this one-step displacement mechanism.
Williamson ether synthesis: A method for preparing ethers by reacting an alkoxide with an alkyl halide. Iodomethane can supply the methyl group when an alkoxide is converted into a methyl ether.
Alkyl halide: An organic compound in which a halogen atom is bonded to an alkyl group. Its methyl group bonded to iodine makes iodomethane an alkyl halide.
Occupational exposure limit: A regulatory or recommended airborne concentration limit for workplace exposure to a hazardous substance. Exposure limits guide controls for workers handling volatile iodomethane.
Alkylation: The transfer of an alkyl group to a molecule or functional group. Iodomethane donates its methyl group to nucleophiles in laboratory synthesis.
Methylation of carboxylates: The conversion of carboxylate ions into methyl esters using a methylating agent. Iodomethane can methylate carboxylates through nucleophilic substitution.