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DBL%20Hendrix%20small.png College chemistry, 1983

Derek Lowe The 2002 Model

Dbl%20new%20portrait%20B%26W.png After 10 years of blogging. . .

Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: derekb.lowe@gmail.com Twitter: Dereklowe

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May 13, 2014

How Many Elements Have You Used, As Elements?

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Posted by Derek

I've written before about how many different elements I've used over the course of my chemical career, but here's a more demanding variant of that question: how many elements have you used in their elemental form? Here's my list - I'm including things that have been transformed, and some that haven't, but I'm not counting structural metals:

Hydrogen (hydrogenations, naturally)
Helium (carrier gas in GC)
Lithium (Barbier reactions, Birch reduction, etc.)
Carbon (decolorizing)
Nitrogen (inert gas)
Oxygen (oxidized a couple of anions over the years, etc.)
Sodium (making alkoxides, Birch reduction)
Magnesium (Grignard formation)
Phosphorus (red phosphorus in a halogenation)
Sulfur (cleaning up mercury!)
Argon (inert gas)
Potassium (drying solvents)
Iron (reduction of nitro groups)
Nickel (as Raney nickel)
Copper (making carbenes, among other things)
Zinc (reductions, zinc-copper couple)
Selenium (as a catalyst in a Kjeldahl, years ago as an undergraduate)
Bromine (many nasty brominations)
Ruthenium (hydrogenation catalyst)
Rhodium (high-pressure hydrogenation, once)
Palladium (hydrogenation)
Silver (well, produced some in a Tollens)
Tin (reduction)
Iodine (Grignard initiation, TLC)
Platinum (hydrogenation)
Mercury (vacuum lines, etc.)

So that takes me to 24 26 elements used in their pure forms, 21 of them as part of actual chemical transformations, more or less. Notable omissions are sulfur, which I don't think I've actually used as elemental sulfur, and chlorine (not quite). There are a few other opportunities (silver, samarium, and indium I've seen used as the metals, for example), but not that many, at least for an organic chemist.

Updates are due to people reminding me of things in the comments! And no, I don't think I've ever used samarium metal itself, although that's certainly another easy one to rack up. As for Raney nickel, it starts out being an aluminum/nickel alloy, but my impression was that the aluminum got pretty well eaten out of it by all that sodium hydroxide. I've made the stuff (once), and a more tedious experience I do not wish for. I've also realized that I used elemental sulfur one time as an undergrad, along with elemental copper, to make cupric sulfide, which is perhaps a more elevated activity than cleaning up mercury spills.

Comments (51) + TrackBacks (0) | Category: Life in the Drug Labs


COMMENTS

1. Alex Whiteside on May 13, 2014 10:42 AM writes...

I assume it's cheating to be a computational chemist in this instance.

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2. Gyges on May 13, 2014 11:07 AM writes...

" assume it's cheating to be a computational chemist in this instance."

Not if you wrote your software from scratch ..

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3. AnonChem on May 13, 2014 11:08 AM writes...

What, no bismuth? :)

From my experiences, bismuth-mediated allylations in water can work okay if the powder mesh size and stirring are optimized.

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4. Anonymous on May 13, 2014 11:10 AM writes...

Derek, I would have figured you would have made Samarium Iodide at some point. No?

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5. Justin Peukon on May 13, 2014 11:11 AM writes...

And what about Al? (so useful as an universal stopper for Erlenmeyer).

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6. Pete on May 13, 2014 11:13 AM writes...

I can't approach your elemental diversity although I did use sulfur to mop up the mercury after I managed to destroy a McLeod gauge. As a teenager, I did use chlorine to gas some flies in a chamber of my own design.

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7. sam adams the dog on May 13, 2014 11:21 AM writes...

Indium, for high-pressure seals.

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8. MTK on May 13, 2014 11:30 AM writes...

Never used sulfur for a mercury spill, Derek?

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9. A Nonny Mouse on May 13, 2014 11:32 AM writes...

Lead??

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10. David Borhani on May 13, 2014 11:37 AM writes...

Hydrogen (hydrogenations)
Helium (carrier gas in GC, degassing in HPLC)
Lithium (making alkyl lithiums)
Beryllium (x-ray transparent window...in my second life...does that count?)
Carbon (decolorizing)
Nitrogen (inert gas)
Oxygen (oxidation of something, I forget what)
Sodium (making bases (typically Na-napthalenide or NaOMe), and drying solvents)
Magnesium (Grignard formation)
Aluminum (reductions)
Sulfur (mopping up Hg)
Chlorine (blanket gas during sublimation of anhydrous FeCl3 --- ugh!)
Argon (inert gas)
Potassium (making bases and drying solvents)
Iron (reduction of nitro groups)
Nickel (hydrogenations, as Raney nickel)
Copper (x-ray anode...does that count?)
Zinc (reductions [nitro groups])
Bromine (nice brominations [hey, it's fun to watch the color disappear as you add Br2 dropwise!])
Rhodium (high-pressure hydrogenation, once)
Palladium (hydrogenation)
Tin (reduction)
Iodine (Grignard initiation, TLC)
Platinum (hydrogenation)
Mercury (vacuum lines, etc.)
Lead (x-ray shielding)

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11. OldLabRat on May 13, 2014 11:38 AM writes...

What, no lead bench tops? I've also used aluminium foil to make an in situ catalyst for a ring closure. Using chlorine gas to do a chlorination is not something I ever intend to repeat. Hopefully, generating elemental silver via a Tollens' test counts.

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12. David Borhani on May 13, 2014 11:42 AM writes...

@11 I was going to add Ag for that reason, but figured that didn't count.

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13. The Iron Chemist on May 13, 2014 11:46 AM writes...

No electrochemistry? That would net me Pt, Ag, and Au.

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14. Justin Peukon on May 13, 2014 11:47 AM writes...

@10 If you include X-ray machines, then add Beryllium (X-ray windows). However, this is not really "chemistry", unless you carried out solid-state reactions under X-ray irradiation...

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15. Justin Peukon on May 13, 2014 11:52 AM writes...

@10 If you include X-ray machines, then add Beryllium (X-ray windows). However, this is not really "chemistry", unless you carried out solid-state reactions under X-ray irradiation...

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16. Anonymous on May 13, 2014 11:52 AM writes...

Mercury - putting a few drops onto the aluminium shell of a 747 to see what happens.

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17. Justin Peukon on May 13, 2014 11:53 AM writes...

@10 If you include X-ray machines, then add Beryllium (X-ray windows). However, this is not really "chemistry", unless you carried out solid-state reactions under X-ray irradiation...

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18. Semichemist on May 13, 2014 12:10 PM writes...

You're all spilling mercury way, way too frequently. Hopefully it was in a cold lab under a hood!

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19. anon the II on May 13, 2014 12:11 PM writes...

In my graduate days there was a lab that kept a big TLC jar full of chloride gas in a hood for TLC visualizations. Basically, you slid back the glass top and using long tongs, waved your TLC plate in the tank for 3 to 5 seconds and then pulled it out, sprayed it with a starch-iodide solution and put it on the ever present and hot hotplate. Primary and secondary amides gave really nice black spots on a white background. When it quit working, you just opened up the chlorine gas tank into the TLC jar for a few seconds to recharge it. The jar had an eerie slight lime color to it. It was just upstairs from my lab so I used it often when doing peptide stuff.

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20. ErrHuman on May 13, 2014 12:24 PM writes...

If we're going to be picky about it, isn't Raney Nickel an alloy with stuff like aluminium in it?

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21. a. nonymaus on May 13, 2014 12:35 PM writes...

Helium, for when you absolutely have to be at 4 K.
Hydrogen for hydrogenations (and deuterium for making the labeled analogue, no tritium yet).
Be windows for in-situ x-ray studies.
(Has anyone used elemental boron?!)
Diamonds are for FTIR.
Nitrogen formed from displacing a diazonium.
Oxygen formed from electrolysis.
Fluorine is something I will not work with (tm).
Ne in the nixies on old instruments
Na in the fire in my hood that someone helpfully started.
Mg Grignards, of course.
Al to make anhydrous AlBr3
Si has a rich surface (photo)chemistry
S in various juvenile pyrotechnics
Chlorine to make anhydrous SnCl4
Argon ion lasers are great for resonance Raman.
Potassium is great for solvent drying and raising insurance premiums.
Titanium is a great electrode material for electrolysis, except when it's not.
Iron in all the cast iron ring-stands that I've been corroding.
Nickel mesh is another great electrode material.
Copper and zinc as melting-point standards.
Played with gallium, never used it for anything.
Brominations are most boldly done with bromine.
Kr is a nice wavelength standard for UV-Vis calibration.
Pd black, the inevitable byproduct of Pd-catalyzed reactions.
Ag mirrors are also inevitable.
I am content to continue not using cadmium in my reactions.
Tin is another interesting electrode material.
The antimony electrode is used in some pH sensors where glass electrodes cannot be used. However, I have a low opinion of it.
Iodine vapor has a very pedagogically interesting UV-vis spectrum.
Tungsten in my lamp filaments and mercury in the manometers rounds it out.

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22. MTK on May 13, 2014 1:06 PM writes...

@18,

Mercury spills were sort of par for the course for us old timers when thermometers were mercury filled.

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23. Chad Jones on May 13, 2014 1:42 PM writes...

1. H2
2. He
3. Ne
4. Ar
5. Kr
6. Xe
7. Br2
8. Cl2
9. O2
10. N2
11. C
12. Al
13. Cu
14. Hg
15. Au
16. Ag
17. Zr
18. Hf
19. Pt
20. Re
21. W

Of course, my list is sort of cheating. I'm not a synthetic chemist, these are just elemental chemicals I've used for other reasons at one time or another. I only included things that are of rather high purity (99ish%).

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24. myma on May 13, 2014 1:48 PM writes...

The analytical balance I used in a few labs had a little "thing" in the back that (I was told) had polonium in it, to reduce static while weighing.

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25. Foolery on May 13, 2014 1:49 PM writes...

Derek, you must have used Samarium!!

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26. oldnuke on May 13, 2014 1:53 PM writes...

Uranium, plutonium, gallium, polonium, ...

Guess it was physics more than chemistry.

Sure was fun shakin' the windows in Las Vegas though - better than anything I ever did in college or my home lab! gr

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27. Virgil on May 13, 2014 2:12 PM writes...

Didn't see Boron there (for example BF3 used to make methyl esters for GC). Also silicon (in chromatography columns of old).
For life scientists, some of the more odd ones commonly used are:

Os and U (electron microscopy stains)
Cs (density gradient centrifugation)
As (phenylarsine oxide, common oxidant)
Rb and Tl (surrogate for K in ion channel assays)

And of course we're all surrounded by walls coated with TiO2.

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28. Anonymous on May 13, 2014 2:20 PM writes...

@ ErrHuman

Raney nickel starts out as an aluminum alloy and then it's treated with sodium hydroxide to leach out the aluminum to leave a spongy nickel with high surface area. That's why you have to wash out the base before you use it. So if the leaching is done well, it's almost a pure metal. I don't know if it's "99ish%" or not. Or should that be "99%ish"?

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29. milkshake on May 13, 2014 2:23 PM writes...

I have seen barium metal used, for preparing BaI2 that is used to make Rieke Ba, that is useful for generating allyl bariums (which alkylate on less hindered carbon, unlike most other allyl metals). Barium ingot is surprisingly dark and hard to cut - the colleague used a metal saw and hammer, to hammer Ba metal chunks into foil, under inverted funnel blowing argon...

Se powder is a nice catalyst if you need for whatever reason to reduce nitroarene to aniline with LiBH4 (there are many better alternatives, but this system has advantage of being homogennous and compatible with solid phase synthesis)

I have seen unforgettable synthesis of ZrBr4 from elements, done by a brave carbohydrate chemist. He would fill a quartz tube with Zr turnings, don welding goggles and then poured straight Br2 down the tube , and collected the nastiness into a beaker at the bottom, (from which he later distilled out Br2 excess and sublimed the residue). The zirconium metal ignited in bromine vapors and glowed bright in the tube like burning magnesium while red-brown vapors were filling the hood...

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30. Derek Lowe on May 13, 2014 2:27 PM writes...

#27 Virgil - I've used plenty of boron and cesium compounds, but never the pure metallic elements. I've been adding to my total element list recently, with some Yb triflate and other things. But using Yb metal, that would be exotic indeed. . .

And Milkshake, I should have known that you'd have some hair-curling experiences to add to the list!

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31. Anonymous on May 13, 2014 3:21 PM writes...

Sodium polysulfide is a good reagent for reducing nitro group and it is prepared from NaOH/NaSH/N2S and elemental S.

Aromatic nitro group can also be reduced by aq NaSH alone if you can maintain the pH alkaline

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32. Anonymous on May 13, 2014 3:31 PM writes...

you can generate chlorine (for aromatic chlorinations) in the lab by adding conc HCl to solid pot permanganate.

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33. MTK on May 13, 2014 3:41 PM writes...

I'm actually not positive about this, but I may have used tellurium once. I remember using diphenyl ditelluride for a Grignard titration, and I seem to recall having to make the diphenyl ditelluride. Just don't recall if I made it from the tellurium metal or not.

So in summation, that's 100% sure I used Ph2Te2, 50% sure I made the Ph2Te2, and completely unsure how I made it. Doesn't matter, I'm saying I did. That's my story and I'm sticking to it.

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34. anonymous on May 13, 2014 4:07 PM writes...

Did I just miss it or has calcium been left out? Am I the only one who has done a dissolving metal reduction with calcium in ammonia? Surely can't be.

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35. isodope on May 13, 2014 4:38 PM writes...

Tritium chemists like to use depleted uranium. (Darn you oldnuke! I was hoping to be the only U guy!) It reacts with hydrogen at room temp to make UH3. Heating releases the hydrogen. A totally reversible process. This is a great way to prepare a fresh batch of T2 any time you need it; otherwise it is sequestered safely as the tritide.

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36. John Schilling on May 13, 2014 4:56 PM writes...

Counting only the elements I have used as rocket propellants:

Hydrogen
Helium
Nitrogen
Oxygen
Aluminum
Argon
Zinc
Iodine
Xenon
Bismuth

And if we count propellant catalysts:

Copper
Iridium

Perhaps fortunately, I missed the opportunity to make fire and plasma with Boron, Fluorine, Mercury, and Cesium.

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37. Curt F. on May 13, 2014 5:56 PM writes...

I am merely a lowly biochemical engineer, not a synthetic chemist. So my list is lamentably shorter than everyone elses

Hydrogen (But only as part of a dilute mixture in anaerobic mix gas so as to avoid mishaps like this one)
Helium (HPLC buffer degassing)
Carbon (does the activated charcoal in the lab milli-Q water system count?)
Nitrogen (inert gas)
Oxygen (made myself from H2O2 and permanganate and also hypochlorite / H2O2 as part of an ill-fated attempt to convert an "anaerobic" culturing hood into a closed chamber for 13-CO2 labeling of aerobes)
Silicon (this was from a previous life where I very briefly worked in microelectronics processing)
Sulfur (not used but made when cleaning up sulfide-containing buffers for drain disposal by mixing with bleach, also used to clean up a fine dispersion of mercury droplets that my gearhead college roommate saw fit to make on our kitchen table. This so disturbed the other chemical engineer and I that we called the fire department but they didn't want to do anything, so he called a professor who recommended sulfur for cleanup, which we obtained and used)
Argon (inert gas)
Silver (does the Ag/AgCl electrode in the pH meter count?)
Platinum (gel electrophoresis does require that platinum electrode)

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38. SteveM on May 13, 2014 6:17 PM writes...

Re: 21. a. nonymaus "Ag mirrors are also inevitable"

Yeah, long ago and far away I silvered some conventional glassware to protect photo-sensitive reagents. I can't even remember where I got the idea.

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39. Anonymous on May 13, 2014 8:01 PM writes...

35: How do you recover the unused tritium? Pass it over more uranium?

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40. petros on May 14, 2014 8:29 AM writes...

No chlorine or aluminium?

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41. Eric Sprague on May 14, 2014 8:40 AM writes...

Would using Zr or Pt crucibles count?

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42. Calvin on May 14, 2014 8:50 AM writes...

To add to many of these which I've had the pleasure of using I can add Ytterbium and Neodymium. In organic synthesis too. The less useful, for me, cousins of samarium.

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43. Jal_Frezi on May 14, 2014 11:21 AM writes...

Elemental sulfur is used in the Gewald synthesis of aminothiophenes, a fantastic reaction.

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44. Jacob from NY on May 14, 2014 12:22 PM writes...

Hydrogen (hydrogenation)
Helium (care and feeding of NMR magnet)
Lithium (active metals demos)
Carbon (decolorizing, et al)
Nitrogen (care and feeding of NMR magnet)
Oxygen (incubator gas)
Neon (spectrum discharge tube)
Sodium (active metals demos)
Magnesium (Grignard, flares)
Aluminum (polishing silver, active metals, covering stuff)
Sulfur (mercury spill, cuprous sulfide demo)
Chlorine (Cl gas generator on the swimming pool, chlorinaton rxns)
Argon (glove box atmosphere)
Potassium (active metals demo)
Calcium (active metals, and I'm sure I used it in a productive way, but I can't remember now)
Vanadium (oxidation states of V teaching lab)
Iron (lots of stuff)
Nickel (Raney Nickel for hydrogenation)
Copper (many things)
Zinc (hydrogen gas generation, active metals demo)
Gallium (melts in your hand, and hopefully not in your mouth!)
Bromine (bromination, and I hope to never see it again)
Krypton (spectrum discharge tube)
Rhodium (does the plating on my ring count?)
Palladium (hydrogenation catalyst, obscure photographic processes)
Silver (electrodes, Tollens)
Tin (activity series demo)
Iodine (TLC visualization, clock reaction variants)
Xenon (spectrum discharge tube)
Cesium (it's yellow and explodes when wet!)
Tungsten (salvaged a filament from a lightbulb)
Iridium (I have an iridium played fountain pen nib)
Platinum (electrodes, hydrogenation)
Gold (electrodes)
Mercury (manometer filling)
Lead (casting things, activity series demo)
Uranium (depleted, Geiger counter demo, cloud chamber source)
Americium (cloud chamber source)

Whew! That's a lot.

Permalink to Comment

45. Sofia.exe on May 14, 2014 12:38 PM writes...

Sulfur and Selenium can used directly for making 2-thione / seleone imidazoles by a particularly mild route I did as an undergrad.

It is probably cheating, but I am gone up and down the transition metals making triflate salts by direct reaction with triflate anhyride / triflic acids.

Permalink to Comment

46. Michael Bower on May 14, 2014 3:16 PM writes...

H2 in a Parr shaker
He as an inert gas
C black to clean things up
N2 as an inert gas
Na to form alkoxides
Mg for a Grignard reagent
S for a thermometer break
Br2 in a bromination of diamantane
Pt in hydrogenations

Not too bad for a computational chemist . . .

Permalink to Comment

47. a. nonymaus on May 15, 2014 10:47 AM writes...

For round 3, how about which elements you have observed via your favourite spectroscopic method (either in elemental form, e.g., the UV-Vis spectrum of neat ozone, or via an element-selective method, e.g., NMR, EXAFS, Moessbauer, etc.)?

Permalink to Comment

48. joeylawn on May 15, 2014 11:52 PM writes...

I'm not a chemist, but I do know some basic chemistry ,like the fact that Mercury loves Sulfur. I once used some sulfur to 'clean up' some spilled mercury from a broken thermometer.

Permalink to Comment

49. Tom Womack on May 17, 2014 10:40 AM writes...

@oldnuke, @isodope: I suppose palladium is expensive, and anywhere you'd got permission to use tritium it is a trivial extra detail also to use uranium; but I'd have expected palladium to be used if you needed a hydrogen sponge. Is palladium's adsorption of hydrogen not so conveniently reversible?

Permalink to Comment

50. Dflan19 on May 21, 2014 8:03 PM writes...

Grad school advisor considered himself a cesium chemist. Thought he could revolutionize aldol chemistry by synthesizing cesium diisopropyl amide. Fellow grad student ordered the elemental cesium, put it in a glove bag only purging the bag with nitrogen once. I knew it was going to be an issue... He scored the ampuole and opened it, BOOM! Project was suspended indefinitely...

Permalink to Comment

51. Dflan19 on May 21, 2014 8:07 PM writes...

Grad school advisor considered himself a cesium chemist. Thought he could revolutionize aldol chemistry by synthesizing cesium diisopropyl amide. Fellow grad student ordered the elemental cesium, put it in a glove bag only purging the bag with nitrogen once. I knew it was going to be an issue... He scored the ampuole and opened it, BOOM! Project was suspended indefinitely...

Permalink to Comment

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