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Methyl Iodide (Makin' methyls)

By moleculeoftheday on October 31, 2006.

Methyl iodide is another simple organoiodide:

Methyl Iodide: InChI=1/CH3I/c1-2/h1H3

Probably the most common lab use is tacking a methyl group onto something; MeI is a great substrate for the SN2 reaction.

Despite its ubiquity, methyl iodide isn't nearly the best alkylating agent. It's cheap and simple, so it sees a lot of use, but there are many things that are better, such as dimethyl sulfate (used a lot industrially, from what I've read), methyl triflate (PDF) (toxic and great), trimethyloxonium salts (my favorite), and the so-called "magic methyl," methyl fluorosulfonate, which has a pretty good vapor pressure (being volatile and such a good methylating agent, magic methyl methylates you,). The latter has been banned in a lot of universities (which is saying a lot, considering how the toxic stuff gets a by in academia).

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Synthesis

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There's icilin, [1.1.1]propellane, helicenes, twistane and its ridiculously large optical rotation absent any chromophores, boromycin, bullvalene and its two-step synthesis, superphane, triquinacene and its non-olefinic properties, tetracyclones plus diaryl acetylenes [4+2] into chicken wire (when was the last time you did a condensed phase reaction at near red heat?), cruise missile fuel, Phil Eaton's momma in the hospital setting up the synthesis of cubane... and you did methyl iodide? Feh.