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Author: Subject: Isocyanide Synthesis
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[*] posted on 12-1-2011 at 14:02


Thanks for the answers, when I will have some time, I will make:

Acetamide ---Hoffman degradation----> Methylamine Hydrochloride -----CHCl3+Base(Ca(OH)2 also works or just NaOH?)---> methyl isocyanide

I would perform the last synthesis in a test tube, just to see how smelly chemical compounds can be. I hope no isocyanate would form though.
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[*] posted on 12-1-2011 at 14:16


Make or buy some aniline and then react that with strong alkali eg alcoholic potash and chloroform.
You can do it on a test tube scale and it stinks like the devil's arse.
It is not toxic by inhalation in quantities that you can tolerate and in my experience it stinks far worse than the aliphatic isonitriles.
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[*] posted on 12-1-2011 at 14:51


I only have phenol, can I make aniline from that? I want to smell that stink :D
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[*] posted on 12-1-2011 at 15:20


Quote: Originally posted by Random  
I only have phenol, can I make aniline from that? I want to smell that stink :D


Not really, the easiest way is benzene -> nitrobenzene -> aniline.
Or you can buy toluene, nitrate it and reduce it to a mixture of tolylamines and then make the mixed isonitriles from them.
They smell pretty awful as well.
It is a lot of work for a nasty pong.
If you can buy or get someone to give you a few mls of aniline and chloroform plus some potassium hydroxide and industrial or bog standard methylated spirit you can do it on a test tube scale.
A couple of hundred mgs of aniline is enough to make a fairly disgusting and penetrating smell.
It was a standard test for arylamines at one time and with hydrogen sulphide et al it accounted for the stinks side of chemistry's bad reputation.
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[*] posted on 29-10-2014 at 09:45


Can urea be used? I tried searching about carbonyl diisocyanide but couldn't find anything
Also, how reactive are they? I read that during distillation there have been reports about explosions (distillation of ethyl isocyanide)
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[*] posted on 29-10-2014 at 13:00


I do not think urea will form isocyanides with those conditions, but likely to form other bad things. ethyl isocyanide should not explode during distillation unless it has been made wrong, it is quite stable albeit stinky as death. Amines like hexyl, benzyl and cyclohexyl make good isocyanides with either base/CHCl3 or TEA/POCl3. But everything they touch will stink. I have made a few of them, and they are some of the nastiest things to smell ever. You just want to vomit suddently when you smell them.
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[*] posted on 6-3-2015 at 23:15


Quote: Originally posted by Fleaker  
Isocyanides and isocyanates are both bad news. I'd keep the hell away from them in an amateur setting and avoid them if at all possible in a professional laboratory.

Methyl isocyanide is extremely poisonous.


The non-volatile isocyanates really are not all that bad to work with so long as you're working in a ventilated space. You just don't want to breath the stuff. Electrophiles of any kind will ravage your lungs. And often your DNA.




I weep at the sight of flaming acetic anhydride.
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