Molecules: You'd better learn to live with them.
Methyl iodide is another simple organoiodide:
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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Comments
MeI as Molecule of the Day? Feh. At least mention the tuft of copper Brillo in the bottle.
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.
Posted by: Uncle Al | October 31, 2006 9:32 PM