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Author: Subject: Phenyl isonitrile: the worst stench ever.
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[*] posted on 8-10-2005 at 14:05
Phenyl isonitrile: the worst stench ever.


Man was that horrible... this stench is so vile, words fail to describe it. Without fume hood I would have thrown up for sure.

I just tried out the isonitrile test for primary arylamines with procedure from Organikum.
5ml Ethanol were put into a small vessel, about 2ml 20% NaOH solution added to it, a few drops of aniline and a few drops of chloroform.
Upon heating the mix quickly became cloudy and separated into two layers, the bottom layer being a small one. I don't know if this is the isonitrile or if the isonitrile is contained in the upper layer.
Then I took the stopper, carefully wafted it
and was greeted with a smell resembling nothing I have ever smelled before, but very bad and absolutely unbearable.

Now I need to know two things: first, how can I completely destroy this substance? Any means of dumping it is out of question. I do NOT want to take it out of my fume hood.

Second, is it toxic and if yes, how much?

I have not been able to find an answer to these questions on google.
Can somebody with access to the right references look it up? That would be very kind.
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[*] posted on 8-10-2005 at 19:00


http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=v82...
Section 2 line 14. It may be of some help. No idea of the toxicity.

[Edited on 9-10-2005 by Mr. Wizard]
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[*] posted on 9-10-2005 at 12:00


Thanks for the link.
I also looked up the original procedure for the isonitrile test (it works with every primary amine of not too high boiling point, so you can use e.g. methylamine, ethylamine or butylamine if you wish to create the stench in your lab) and it told that the isonitrile should be hydrolyzed with conc. HCl after a positive test.

It also said that isonitriles were very toxic!:o
I'm theorizing that this is due to the -NC group being loosely attached and having a considerably higher energy than the nitrile.
The resulting cyanide ion could be the source of the toxicity.
Or the isonitrile adds to random functional groups in the body and causes long- lasting organ or nerve damage...

I really need more infos about isonitriles... google turns up almost nothing useful.
The toxicity wasn't mentioned in any search result!
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[*] posted on 12-10-2005 at 05:15


Adding some HCl and shaking the vial completely decomposed the isonitrile in a matter of seconds.
It was really surprising to note how the smell of the substance went from absolutely horrible before the addition to almost odorless after the addition and shaking.
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[*] posted on 9-6-2006 at 11:48


The worst stench ever huh….
Last night after reading that, I thought well of course we must make it! In retrospect I wish I hadn’t.

The smell is indescribable. Not that it is so ungodly beyond all expected levels of stink, which it approaches, but more it is like nothing you have ever experienced and your brain while certainly repulsed to the extream, struggles to define it. A double assault at your senses. It has a persistent linger on everything that comes near it including your neurons. Much like a horrible picture you see that can’t be purged from your mind. Even after the scene changes you are left with a ghost difficult to eradicate.
While HCL + alcohol cleans off hard surfaces well, it does nothing for your memory.

[Edited on 9-6-2006 by ordenblitz]

[Edited on 10-6-2006 by ordenblitz]

[Edited on 10-6-2006 by ordenblitz]
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[*] posted on 9-6-2006 at 15:27


I'd like to find more about this, applications, uses of isonitriles. Very interesting, because of hte nice negative charge the N+ of -NC puts on the neighbouring carbon. But you are right, there is very little info on this on the net.

Anyway, here is another reaction mechanism to isonitrile, using cyanide and halogenoalkane:

The main product is the nitrile, however, while the isonitrile should be noticable by smell. Remarkably the reaction can occur in water/EtOH mixture. I imagine, this equilibrium between the isonitrile is similar to the reaction of CH3I and NaNO2, where you get the nitrite and nitromethane at the same time.

I am also curious as to the stench, can you describe it somewhat? Damn I have to make it.
The reason why I am asking, why would something that the body during evolution is never exposed to, develop a sense of smell for R-NC?
In other words, if you can smell something, it is likely a combination of several smell receptors that are triggered at the same time, so the smell must remind you of *something*!
Or more to the point, are smells of 100% unnatural substances truly unique, or just unique concoction of certain triggered neurons which normally respond to other stimuli?

[Edited on 9-6-2006 by chemoleo]




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[*] posted on 9-6-2006 at 16:55


I have no good description for it.

Besides me, the two other people nearby, who were brave enough to try it (one an inorganic chemist, the other a pyro) had the same thing to say, "I can't describe it but it sure is horrible".

There does not seem to be a way to smell it only slightly from the vial or stopper. I mean if you get enough of it to register, it’s enough to saturate your senses. Very strange threshold. Initial exposure goes like this…You know it’s going to smell so you try very hard to not get a big whiff by waving the stopper or wafting the air near the flask with your hand, getting braver every attempt until.. Bingo! It’s actually funny to watch someone’s reaction when it finally sets in. It’s a very strange face. Best description would be incredulous repulsion! Possibly dilution in some other solvent would provide a means of smelling it without all the mental fireworks.

It took an hour and a half gallon of IPA99%/HCL32% to clean that smell out of my hood. If you do it, plan to spend some time de-stinking after. The smell is something you don’t want to ever enjoy again. Tiny whiffs of remnant traces on the hood tended remind my nose of the full scale event and I dreaded it.
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[*] posted on 9-6-2006 at 17:55
Phenyl isonitrile: the worst stench ever.


As an ER physician for the past 20 years I have encountered some amazingly hellish aromas. Your desciption of the monster you created in your lab is quite vivid and delightful. Could your product smell worse than some of the champion stinks of biological origin? Among the worst I can remember include the pus from large peri-rectal abscesses (but-boils), or other case where anaerobic microbes work on proteinaceous detritus at body temperature. Equally horrendous but subtly different is the stink of melena - stool containing fermenting blood from hemorrhage within the lower GI tract. Something about the action of gut bacteria upon the hemoglobin molecule releases a volatile product so exquisitely stinky that I am wondering if it could be in any way chemically related to your product.
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[*] posted on 9-6-2006 at 19:04


It's hard to characterize worst but this stuff probably can’t be called the most awful. Mainly its effects are mental not physical. In my opinion there are more fowl smells like mercaptans, pentamethylenediamine, butanediamine etc. Said nasties are, in terms of your immediate response; gagging, choking, retching, evoke greater physiological effects that make them largely more repellant. So in that regard isonitrile is not going to win the title but certainly is heinous.
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[*] posted on 12-6-2006 at 03:58


Orderblitz, you've made me very anxious about this substance. I have the chemicals for making this. What about making a ml or so in my backyard? At least the stink then is not inside and does not cling to all kind of items in my lab and/or house. Doing this outside seems to be a fairly good way of trying this.

I've no other intentions with this chemical than just experiencing what you describe. What is your opinion on this? Do you expect any problems if I do this outside? My nearest neighbours are about 30 meters from my house, but if wind is from the right direction, then the air is blown towards a meadow on the other side of the house.




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[*] posted on 12-6-2006 at 05:59


Concerning toxicity:

from http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV6...:

"Many isocyanides are reported to exhibit no appreciable toxicity to mammals. See J. A. Green II and P. T. Hoffmann in "Isonitrile Chemistry," I. Ugi, Ed., Academic Press, New York, 1971, p. 2. However, since certain isocyanides are highly toxic (e.g., 1,4-diisocyanobutane), the checkers recommend that all isocyanides be handled with due caution. "

Apparantly methyl isonitrile binds with hemoglobin beta chains according to Journal of Molecular Biology 81, 2 (1973) 199-205




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[*] posted on 12-6-2006 at 06:42


OK, I exaggerated about the stench... but its still something you don't want to spill.

As it isn't a gas, but a high- boiling liquid, the stench will stay inside the test tube if not spilled or boiled excessively.
I did the preparation inside my fume hood, and didn't have to clean it afterwards. The smell didn't cling to the walls. Only the reaction mix smelled, nothing else afterwards.




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[*] posted on 12-6-2006 at 09:18


Oh, stenches. I've never smelled said isonitrile, but the worst stench I have ever smelled is something that emanates from my lab's refrigerator. I have no clue what the stuff is, but good grief, it's foul. Think fishy vomit on a hot July day. One of the professors told me they inherited the fridge from another lab, and in the process of moving, it sat outside in the sun for a while with some sort of real stinkoid in it. And the fact that we keep pyridine, acetaldehyde, and 2,3-butanedione in this thing does not help. *shiver*
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[*] posted on 12-6-2006 at 17:07


Cleaning of my hood was only necessarybecause I used a small flask and heated with a torch. Hot spots caused some spattering from the mouth of the erlenmeyer, so I had some destinking to do.

If done properly one only has to clean the glassware.
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[*] posted on 26-5-2013 at 22:45
An Olfactory Challenge


Could anybody mix a drop of chloroform with some aniline in a test tube, and add a drop of alcoholic potassium hydroxide? And describe the smell to me?

[Edited on 27-5-2013 by Polesch]
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[*] posted on 27-5-2013 at 12:25


This experiment already is described here (I think by user garage chemist) and the effect was not fun at all. Based on that description I dared not repeat that experiment, the smell apparently is sooooo bad, that it will make you vomit. You could use the search engine to find thread which I mention.

EDIT: Found the thread: http://www.sciencemadness.org/talk/viewthread.php?tid=4621#p...



[Edited on 27-5-13 by woelen]




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[*] posted on 27-5-2013 at 12:51


AFter reading the thread I have a question. Woelen, did you smell it??



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[*] posted on 27-5-2013 at 14:19


What are the reaction products?



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[*] posted on 27-5-2013 at 14:44


Phenyl isocyanide, apparently. I'm not interested in trying it- I remember having to work with phenyl isothiocyanide once, and that was enough for me.



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[*] posted on 27-5-2013 at 23:43


Quote: Originally posted by Eddygp  
AFter reading the thread I have a question. Woelen, did you smell it??
No, I did not do that experiment, although I have the reagents. I do not want to vomit, and I do not want to stink up the neighbourhood.



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[*] posted on 8-12-2013 at 18:04


Phenyl isocyanide smells awful but it is not really revolting.
MeSeH smells far worse in my opinion.
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[*] posted on 8-12-2013 at 22:10


All of the isonitriles have a bad smell, but they are pussycats compared with some other compounds. Phenyl isonitrile does not have a particularly low level of detection so you can do this experiment outside without difficulty. As a schoolboy, long ago it seems, I used to annoy my sisters with it, and I took every excuse that I could find to make it during my education, as it is a diagnostic test for primary amines.

But you should never sniff a reaction. Waft some air over it or pour some out into a watch glass.

Another one. Take some iodine saturated in acetone, say 4 ml, and add a drop of concentrated nitric acid. Warm it a bit and after a minute the iodine colour will disappear. If not, then add another drop. When clear pour some out where it can evaporate. I did this one during my education too, and they never discovered who did it.
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[*] posted on 10-12-2013 at 10:36


What would the last one form, Paddywhacker?
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[*] posted on 10-12-2013 at 10:58


Iodoacetone:

http://www.sciencemadness.org/talk/viewthread.php?tid=12193




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[*] posted on 10-12-2013 at 15:56


Oh im excited. I have all the reagents for this.. Ill make a video of my lab mates trying to describe the smell if it is as bad as you say.



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