Pyridine (Smellier benzene)

Pyridine is simply benzene with a nitrogen substituted for one of the CHs:

i-0959281379377338b509df8ceeb395db-pyridine.gif

Such a simple change has myriad effects. The addition of the electronegative nitrogen makes pyridine a good base (it's commonly used in reactions that generate protons to mop up the acid as you go). The same change makes it miscible with water (benzene is only about 0.2% soluble).

Most importantly, however, pyridine stinks. Even at high dilution. It's not a normal piercing chemical scent, either, it has a distinct biological richness that the nitrogenous heterocycles seem to deliver on especially well (witness the intensely fecal indole, for another example). Benzene smells rather pleasantly like gasoline (Both are pretty toxic, by the way), but pyridine smells like an unventilated room full of the infirm and dying.

It's been awhile since we got into stink and I don't want you to walk away thinking this is the worst stuff ever, so expect a few more this week!

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Vince, I wonder how cool you think this is: Pyridine is known to reduce male fertility!

By olchemist (not verified) on 25 Sep 2007 #permalink

Pyridine at high concentrations will fatigue your nose and smell vaguely sweet, ditto H2S. Isonitriles will seize your guts and squeeze hard all the way to your grave. They generally don't make pretty colors with middle and late transition metals, either.

Yah, but, c'mon. It's still fun. And when things smell really bad (ie, pyridine) I try not to inhale a whole butt load.

By Vince Noir (not verified) on 25 Sep 2007 #permalink

I recall finding the benzinous smell of gasoline quite pleasant as a child. I am now well on my way to becoming an attorney . . . although I don't think this is causal at all.

Oh man that stuff's nasty-smelling. Those two or three of you who are hard-core Mark Leyner fans will recognize the phrase "Lincoln's morning breath" -- that about sums it up.

olchmist:

The 'ability' of pyridine to reduce male fertility is nothing more than an urban myth. I'd like to see a legitimate reference that accurately describes this...

By around the cor… (not verified) on 26 Sep 2007 #permalink

@the guy down the hall

I want to see the one who volunteers for some accurate tests. In any case the myth is strong enough to be mentioned on safety data sheets and I am not taking the chance ;o)

By olchemist (not verified) on 27 Sep 2007 #permalink

Oh man, I was using pyridine the other day and my lab's post-doc walked in, took one sniff, and left. He then called me on my cellphone and told me that he wasn't going to be back until the next day because he couldn't stand the stench.

want to see the one who volunteers for some accurate tests. In any case the myth is strong enough to be mentioned on safety data sheets and I am not taking the chance ;o

We used pyridine a lot in my days as a lab technician. I say 'a lot', we used it for one test that we drew lots for, in order to avoid doing. Open the bottle and you would clear the room of people. The smell really did grab you hard and took a while to let go.

Probably exposed to it once a week for three years.

I have had six children since so I guess the 'fertility loss' is a bit of a myth.

By Phil Jones (not verified) on 26 Jan 2010 #permalink

Pyridine is reduce male-fertility?!if reduce then how much time take for this process because iam always done reactions using the pyridine., lease tell answer..,.

By laxminarayana.b (not verified) on 20 May 2010 #permalink