Smelliest Compound

If you make your own perfume or solid perfume, the goal is to make something that smells pretty. However, some perfumes smell truly horrible. What do you think you could add to your perfume to make it as bad-smelling as possible? How about thioacetone? Here's an email I received regarding the smelliest compound:

Hi Anne Marie,

I retired about 8 years ago, but I still enjoy reading your "about chemistry" articles.

You may be interested in the history of the worst-smelling compound known, thioacetone.

Thioacetone (CH₃)₂C=S was first produced in Freiburg, Germany in 1889 by pyrolysis of its cyclic trimer. The laboratory workers were protected by their efficient fume hoods, but people were fainting in the streets about two miles away. The City Council ordered that the laboratory be shut down!

However, it is not quite true that the whole city had to be evacuated, although there was certainly plenty of panic. You can read about in the following (page 4). You will note that the suggestion that the smelly material was propane-2,2-dithiol doesn't fit the stoichiometry. That would require a source of hydrogen sulfide.

http://www.oup.co.uk/pdf/bt/orgchem/chapter01.pdf

I first found out about thioacetone from the original German as a PhD student. I was searching for something to disrupt an undergraduate function, but decided thioacetone was just too dangerous (we settled for bromoacetone).

I actually experienced its unbelievable odour, far worse than that of any skunk, while Safety Officer in the Chemistry Department at Monash University, Melbourne, Australia.

It turned out that the spectroscopists were working with a rather unusual sulfur-boron compound which had reacted with the residual acetone used to clean some large ground glass joints. The amount of thioacetone that could be produced in this way was miniscule, but it affected the whole campus.

Mick Fuller

Ok, maybe thioacetone wouldn't be a good compound to synthesize and play with, but bromoacetone... hmm. Thanks for the email, Mick.

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