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Thiophene (Sulfur, not quite stinky)

Category: Synthesis
Posted on: October 17, 2007 7:27 PM, by Molecule of the Day

Thiophene is a simple five-membered sulfur-containing heterocycle - it's the sulfur analogue of furan.

InChI: InChI=1/C4H4S/c1-2-4-5-3-1/h1-4H InChIKey: InChIKey=YTPLMLYBLZKORZ-UHFFFAOYAY


It's an interesting heterocycle in its own right but it's probably best known as a contaminant in benzene - almost all the bottles you get a hold of today proclaim they're "thiophene free."


It wasn't always the case, as chemists who were trained more than a decade or two ago will tell you. My advisor in undergrad told me stories about having to remove the thiophene from benzene, which entailed shaking the benzene with concentrated sulfuric acid in a giant separatory funnel. Pressure builds up as you use them, so you have to open the valve to vent them. Inevitably this releases some liquid; in this case a caustic/carcinogenic sulfuric acid/benzene mixture.


My boss was, generally, far from cavalier about chemical hazards, but his quips were the best. "You'll get hit by a bus before this stuff gets you." "We all have to go sometime!" Or, when wiping up (gloveless) a concentrated (deep red) ethidium bromide spill, "I'm too old to worry about this intercalator shit!"


For the record, he was a careful guy in general (and all in all, pretty safe). Hi, if you're reading :) The ethidium one even made my jaw drop a bit, though (and I'm skeptical about the level of risk 1 micromolar ethidium stain really poses, as I mentioned). I still wear gloves, though!

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Comments

Look at the ages of chemists dying today. Benzene and carbon tet won't kill you before the EPA and Homeland Severity make suicide a joyful contemplation.

Uncle Al, "I'm homicidally depressed."
Psychologist, "You mean 'suicidally depressed'."
Uncle Al , "(waits the beat)... my way is better."

Posted by: Uncle Al | October 17, 2007 8:56 PM

Man if only I knew what terrible things I've spilled on myself during my brief time as a chemist....Makes me worried. But I find I still have less chemophobia than most.

Posted by: Vince Noir | October 18, 2007 2:09 AM

I worked in as lab in which a PhD student made selenophene as a starting product for a heavy metal precipitant. Did that ever stink!!! I emigrated shortly after the boss suggested that I might do my PhD on the tellurium analog.

Posted by: killlinchy | October 20, 2007 12:21 PM

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