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Topic: Destroying methyl iodide in reaction  (Read 7707 times)

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Offline africanol1

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Destroying methyl iodide in reaction
« on: August 29, 2015, 03:52:57 PM »
Dear community,


i had a reaction, in which i used methyl iodide. the corresponding reaction was an methylation reaction of activated enolates via LDA in THF. To get rid of the unreacted MeI i used a saturated ammonium chloride solution (i used 0.5 ml MeI and to be sure i put 10 ml of that saturated solution into the reaction mixture).
after sepratation of both phases, i evapotaed the THF. i know that in general, methyl iodide can be destroyed with every amine. but because of the high toxicity of MeI i am not entirely sure, that the saturated NH4Cl solution and the amount i used was enough to quench it. now i am scared, that i inhalated something of the MeI ^^".


Are my worries for no reason?

Best

Offline phth

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Re: Destroying methyl iodide in reaction
« Reply #1 on: August 30, 2015, 06:18:57 PM »
Just run it through a column.  It's a labile SN2 electrophile and will react with nucleophilic SiO2 unless you're trying to generate the enol ether

Offline Archer

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Re: Destroying methyl iodide in reaction
« Reply #2 on: September 01, 2015, 10:23:57 PM »

Are my worries for no reason?


When you are handling substances like this, worries are never for no reason. If people are not worried about handling methylation agents I tend to point them in the direction of reported injuries etc.

You probably didn't inhale a great deal of MeI, look at worst case scenario. No reaction, no destruction of MeI during work up so all MeI going in may come out again.

Most of the residue would have ended up in the solvent trap for the distillation.

I tend to use freebase amines to quench methylation reactions. I avoid MeI because it disproportionates during storage and prior to use you have to remove the I2 before you can begin the reaction.

If you are concerned, speak with a Doctor of Medicine.
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