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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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« Things I Won't Work With: Straight Dimethyl Zinc | Main | Reduce Your Number of Reductions, Why Don't You? »

October 26, 2009

Elements I Have Yet to Use

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Posted by Derek

I wrote about this topic a few years ago, and thought I'd update it. Many chemists find themselves looking at a periodic table and wondering "How many of these things have I personally handled?" My list is up to nearly 45 elements (there are a couple that I've got to think about, one-off catalyst reactions from twenty-two years ago and the like). And there are at least 29 that I hope to never use at all, since they're radioactive and I'm generally not in the mood for that. So what does that leave me?

Well, I've never used beryllium, although it's not that I'm tapping my foot waiting for any. It's pretty toxic stuff, for the most part, and there are hardly any organic chemistry reactions that get near it. That means that I can't even think what I might use it for, and I could easily go my whole career without seeing any.

The next lowest molecule weight element I haven't messed with (excluding unreactive neon, which you at least get to see in its excited state) is probably scandium. That whole first column of transition metals is pretty useless for organic chemists, to be honest (Yttrium? Lanthanum?), and I've never seen any reactions that leapt out at me as things I had to try. No, if the answer is scandium, it must have been a pretty odd question.

Next up, I haven't used either of the G twins, gallium and germanium. They're not too well studied compared to their family members above and below: aluminum and even indium are more widely used than gallium, and silicon and tin show up in organic labs a million times more often than germanium. But with those relatives, you'd have to think that there's something interesting that can be done with these, so it depends on whether anyone finds out what that might be during the rest of my chemistry career.

And right next to these is arsenic, which I've also managed to avoid. It's famously poisonous, although it's really not worse than a lot of other things that get used much more often. But again, there's not a lot of compelling chemistry to be done with the stuff, not that I know of, anyway, and there are always those unfortunate nomenclature problems to be dealt with, especially if you have a British accent.

Krypton I've never had a use for, and I'd have to rate the chances as very low indeed. In the next row, I've handled strontium chloride, but only to make red-colored flames for a school demonstration show. I have yet to touch yttrium, as mentioned above, and I've managed to miss zirconium so far as well. There are actually a number of organometallic reactions that use that one, so it's at least a real possibility. Niobium I have yet to encounter, and at the rate it's used, I probably never will. Cadmium's another toxic beast - there are some old reactions that use organocadmiums, but I can't think when I saw a modern reference that used any of them, and I don't see this one in my future, either. Antimony I might use if I never need some horrible superacid. Tellurium, well. . .there would have to be a pretty good reason, given its reeking, nose-wrinkling sulfur and selenium relatives, but someone might yet come up with one. Can't rule that one out, unfortunately.

Now we're getting into the heavy metals, and a lot of gaps start to appear. Has anyone in an organic chemistry lab ever used hafnium or tantalum? Didn't think so. The best candidate for "something I could use, but haven't" in this bunch is osmium. The tetroxide is a very useful reagent that I just haven't had the need for. It wouldn't surprise me if that's the next addition to my list. I've no desire whatsoever to use thallium. It's part of a short run of nasties that you hit right after the jewelry metals - you have your platinum, then gold, and you think you're in the high-rent district, and suddenly it's mercury, thallium, and lead right in a row. Reminds me of the way towns were stuck next to each other in New Jersey.

And as far as the lanthanides, well, I've used cerium as a TLC stain, and once I used samarium iodide - which, true to its reputation, didn't work. None of the others have I touched, and unless I need some funky NMR shift reagent, which fewer and fewer people do these days, I don't see it happening. There are a lot of funny rare earths down there, but little reason for an organic chemist to go digging around among them.

Weirdest element I actually have handled? Xenon would have to be the winner - I've used the difluoride, and yes, that was the recourse of a desperate chemist. But it did work to turn a silyl enol ether into an alpha-fluoro ketone, so I can't say anything bad about it, other than its rather penetrating smell, which I probably should have taken more care not to experience. . .

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


COMMENTS

1. metaphysician on October 26, 2009 8:40 AM writes...

"if the answer is scandium, it must have been a pretty odd question." "you think you're in the high-rent district, and suddenly it's mercury, thallium, and lead right in a row."

It can't be said often enough, you have a talent for words.

Also, while its not an element per se, have you ever used deuterium?

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2. Torontochem on October 26, 2009 8:45 AM writes...

I've been in the strange position to have used several of the Lanthanum series elements. Of course these were all to make organometallic complexes that looked real pretty.

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3. HappyDog on October 26, 2009 9:10 AM writes...

My training is in Biochemistry, and in grad school I worked several years in an x-ray crystallography lab. I had the great (mis)fortune of working with such charming elements as lead, mercury, and uranium to synthesize heavy atom containing compounds for anomalous dispersion methods. I actually worked with uranyl acetate. Fortunately, the commercial versions are less toxic, but that was still an unpleasant experience. On a side note, not that I've used beryllium in synthesis, but I've also had to screw around with a rotating copper anode when we had a problem with our vacuum. I had to make sure I didn't touch the nice beryllim window that was right near my workspace!

After that, a job as a computational chemist looked really good. And safe!

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4. Eric on October 26, 2009 9:14 AM writes...

Metaphysician, pretty much all organic chemists use deuterated solvents in their day-to-day NMR work, and when they're characterizing reaction mechanisms or verifying structures, deuterated reagents can be quite handy.

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5. petros on October 26, 2009 9:27 AM writes...

Ceric ammonium nitrate is a fairly common reagent

But I'd agree about most of the others

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6. Slothy on October 26, 2009 9:27 AM writes...

I can't speak about the smell of xenon, having never experienced it myself, but there are other reasons why one might want to avoid breathing too much of it: elemental xenon produces anesthetic effects that are about 50% more potent than N2O.

Then again, there is at least one reason why you WOULD want to breath xenon gas: it lowers the pitch of your voice, just as helium raises it. And nothing quite justifies the advancement of science like a silly demonstration.

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7. DrSnowboard on October 26, 2009 9:29 AM writes...

Scandium triflate is a useful Lewis acid I believe, not decomposed by aq...

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8. barry on October 26, 2009 9:33 AM writes...

My list would look similar. A labmate in grad school did have recourse to hydrogen telluride as a reductant once. We were all relieved that it didn't work. It smells worse than H2Se, which in turn smells worse than H2S. We never could rationalize why the human genome preserves a receptor for H2Te.

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9. John Spevacek on October 26, 2009 9:53 AM writes...

I've used lanthium when I needed to make an implant radiopaque.

And as to hafnium, that is used to calibrate UV/Vis spectrophotometers, so while you may not use it directly, it is still there just behind the scene.

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10. CMCguy on October 26, 2009 9:53 AM writes...

Stimulating entry although made me consider that not long ago you wrote a post "complaining" about too many procedures to do particular transformation(s) whereas IMO this one illustrates how dull Org Syn portfolios would be without those who do look for different ways to do the same thing. Granted many things are exotic or choice of desperate (and rarely likely to be useful at scale) but if the inorganic and organometallic chemists weren't looking at "weird" stuff most the syn types would be too lazy investigate new and interesting reactions as they cobble through a total synthesis.

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11. David P on October 26, 2009 9:54 AM writes...

I'll back up Dr Snowboard for scandium triflate - I have seen it used to great effect.

As for cadmium - what, no rechargeable batteries? Or does that not count?

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12. RM on October 26, 2009 9:54 AM writes...

You'd have to expand the list if you aren't limiting yourself to "added it to a flask as a reagent".

Cadmium is in nickel-cadmium batteries, which are probably in some equipment or another in the lab. Tantalum is in tantalum capacitors, which certainly are in any modern lab equipment. The maligned yttrium is found in computer monitors and certain LEDs. And if you've ever used a "flint" striker to start a bunsen burner, you've used ferrocerium, a mixture of iron, cerium, lanthanum, neodymium, praseodymium and magnesium.

"Chemistry in its element" from the (British) Royal Society of Chemistry is a good (short) weekly podcast about the elements and their various uses. I'd recommend it: http://www.rsc.org/chemistryworld/podcast/element.asp

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13. KB on October 26, 2009 10:32 AM writes...

The Lanthanides. Lovely bunch of metals but require patience, luck and practice to prepare. SmI2 gets a bad rep but once you know how to prepare it reliably (forget the Aldrich stuff, it's mainly SmI3) then that deep blue never fails to seduce. Unlike cadmium which I had the pleasure of using during my PhD. Horrible stuff. Didn't even do the transformation. Crap.

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14. lukas on October 26, 2009 10:34 AM writes...

Slothy #6,

he was talking about the smell of XeF2, a powerful fluorinating agent. Not something you would want to get anywhere near you, especially not the nose.

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15. retread on October 26, 2009 10:41 AM writes...

I have sort of a converse question. Why are Ruthenium and Molybdenum used (seemingly exclusively) for metathesis? Have other 4 f elements been tried and found wanting? If so, what about using their congeners in 3f (E.g. Fe, Cr) or in 5f (Os, W). It can't be a problem with availability. It also can't be unfamiliarity, as even in the 60s OsO4 was widely used. Any thoughts?

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16. DrKai on October 26, 2009 10:44 AM writes...

I'm also a crystallographer with the 'pleasure' of working with a number of toxic chemicals and heavy metals for protein crystal soaking experiments.

Until Derek pointed it out, I was unaware of the unfortunately named arsenic compound 'arsole'. My favorite stealth arsenic compound is cacodylate. Somehow there are a number of crystallization solutions that use cacodylate as a buffer.

Always funny to ask biochemists if they know that their cacodylate buffer is actually the arsenic-containing solution with the formula (CH3)2AsO2H.

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17. Ralos on October 26, 2009 10:47 AM writes...

While I was getting my BS, I made some lanthanide complexes. Remembering making lanthanide perchlorates as starting materials, what fun! During my PhD, I did work with arsenic and antimony with transition metals. Your right, pretty nasty stuff arsenic and antimony. My prof made us get manditory blood tests every two months to make sure we were not poisoning ourselves. Made some pretty interesting cooridination complexes and catalysts though.

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18. Atticus on October 26, 2009 11:01 AM writes...

Unless you count the stuff bathing the magnet in the NMR, I've never had to use helium (in the lab anyway).

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19. CMCguy on October 26, 2009 11:04 AM writes...

A slight tangent but do not forget that "modern medchem" has it's roots in arsenic as Paul Ehrlich's "magic bullet" to treat syphilis was such a compound. I do not know if still is the case but deworm drugs for dogs used to be arsenic derivatives.

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20. Big Bad Chem Daddy on October 26, 2009 11:05 AM writes...

Surprised that you've never used arsenic as a ligand; triphenylarsine helped me out of a spot once, and it's not terribly uncommon.

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21. Vadedr on October 26, 2009 11:16 AM writes...

Indeed; I had to have a dachshund treated with an arsenical for heartworm. Poor beast was confined to a cage for a month so little bits of dead worm wouldn't come loose and give her a pulmonary embolism.

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22. Felix on October 26, 2009 11:18 AM writes...

Germanium has been used to advantage by Piers et. al. (J. Org. Chem. 1990, 55(11), 3454, DOI: 10.1021/jo00298a014). A vinyltrimethylgermanium derivative is robust enough to withstand a cuprate addition but is readily converted to the vinyl iodide for a Nozaki-Hiyama coupling.

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23. David P on October 26, 2009 11:24 AM writes...

There is also melarsoprol, a treatment for sleeping sickness and Chagas' Disease. Though from what I understand it is not the medicine of choice. (/understatement)

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24. David P on October 26, 2009 11:31 AM writes...

I was going to say, I was surprised that you have never used OsO4 or any of the related osmates. Never needed a dihydroxylation? Or prefer to use ozone for a olefin cleavage?

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25. MiddleO'Nowhere on October 26, 2009 11:45 AM writes...

I took an inorganic class in which we did reactions with something like 82 of the 94 naturally occurring elements, including uranium salts and thallium metal. Mostly we worked with salts and attempted to oxidize and reduce them to all of their possible oxidation states as well as precipitating them with various counter ions. It was an interesting way to look at trends in the periodic table. Plus there were a lot of pretty colors. Gold hydroxide is especially pretty I think. In a second inorganic class, we actually attempted to make XeF2 from fluorine and xenon gas.

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26. Hap on October 26, 2009 12:42 PM writes...

I was surprised that you hadn't used Zr for Negishi couplings, though in anywhere but total synthesis it seems kind of atom-expensive.

I wonder how Kishi et al came up with Tl for Suzuki couplings - I don't know whether it's better than organolead reagents, and it has to be better than the dreaded Me2Hg, but I would have had to get far down on my list of bases to get to Tl (ethoxide or hydroxide?).

I think Sc is the answer to the question, "How can I get an Org Lett paper?"

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27. milkshake on October 26, 2009 1:33 PM writes...

Sc and rare earth triflates as LA are pretty useful in Mukayama aldol and hetero Diels-Alder - I suppose its not done much in idustry labs.

Be would be pretty useful if it was not as super-allergenic. There are reductive coupling reactions of acyl chlorides with Be powder that go through RCOBeX species thus providing acyl anion equivalent - pretty neat transformation unfortunately Be has to be used stoechiometrically.

I made (and used) dimethyl cadmium once, a lazy cousin of dimethyl zinc. It was for the PhePClMe from PhePCl2 and it actually worked but the phosphine smell and tedious de-complexation precedure (Cd sticks to the product) was no fun.

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28. Andrew on October 26, 2009 2:28 PM writes...

Whilst it may be cheating, tantalum plugs are used to repair Glass line reactors when some oe cracks the lining. Most Process chemists will have used a plugged reactor at some time given the heavy handed nature of process operators.

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29. TAK on October 26, 2009 4:42 PM writes...

Retread #15

As a Grubbs PhD, I can say that just about every reasonable element was tried to make metathesis catalysts (including U - didn't work). W and Ta actually both work very well, but are less water stable than Mo. Other metals make carbenes that are too stable to react, or do alpha elimination, etc.

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30. JK on October 26, 2009 6:25 PM writes...

Well, some time ago as a low temperature physicist I used beryllium-copper in a torsional oscillator, made a thermometer for measuring temperatures millikelvins above absolute zero from the magnetism of lanthanum cerium magnesium nitrate, made magnetic shielding out of niobium (it's a nice superconductor), indium formed nice leak tight seals, gallium arsenic can semiconduct at low temperature for signal amplification. Next door people were studying low temperature magnetism in holmium and dysprosium.

In undergraduate physics the noble gases were the favourite source of data for lecturers on statistical mechanics. Properties of solids, liquids and gases like heat capacity, diffusion, etc come out surprisingly accurately even for simplifying assumptions. They really are a bit like billiard balls. Nice for physicists but a bit boring for chemists.

Now I'm a biologist - proteins and lipids. I still build some of my own equipment but certainly use less exotic materials than I used to - plastics, glass, steel, epoxy glues, etc. Photolithography for microfluidics is done on silicon crstal wafers, but the photochemistry and etching is organic.

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31. non-pharma chemist on October 26, 2009 7:45 PM writes...

Hey, all chemists play this game from time to time. I remember when I met Fagan, he said his goal was to work with every element in the periodic table (I guess excluding the barely-existing actinides). I kind of have categories.

Favorite: Iridium (for the doctorate! yayyy Iridium! Yaayyy!)
Most Deadly: Thallium (Boo!)
Most Disappointing: Tie between Vanadium and Nickel (so many bad procedures for each)
Most Bang for the Buck: Titanium (Such awesome chemistry - such awesome prices!)

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32. Kuchs on October 26, 2009 9:41 PM writes...

I had the fortunate (unfortunate) time of using ziconyl nitrate in an attempt to nitrate a very deactivated and hindered substrate and it worked...kind of...

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33. SRC on October 26, 2009 9:48 PM writes...

"next lowest molecule weight element"

C'mon, Derek. You've been hanging around too many molecular biologists, who refer to everything as a "molecule" (including elements and ionic compounds), regardless of whether it is or not. Abandon the molecular biologists and get back with the scientists. It's "atomic" weight.

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34. Shane on October 26, 2009 9:50 PM writes...

Cadmium is used sometimes in NMR experiments as a stand in for calcium in binding studies. Not nice to handle but nicer to handle in salt form than organic form.

Do the heavier alkali metals get used for anything?

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35. psi*psi on October 26, 2009 11:24 PM writes...

Probably the weirdest things I've used thus far are yttrium, tungsten & cadmium.
#34: I'm pretty sure cesium carbonate goes into some Pd-catalyzed couplings. We devicey folk sometimes use CsF as a thin layer over Al cathodes to block holes and such.

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36. milkshake on October 27, 2009 1:15 AM writes...

Cs-carbonate and Cs-fluoride are very useful, nice mild bases that provide the advantage of increased solubility of Cs salts in the organic solvents - medicinal chemists use them all the time; Cs salts are not cheap but they save the troubles with using crown ethers, or with much stronger bases like NaOtBu. I have also used cesium formate in asymmetric hydrogenation. (Cs formate is getting affordable because it is used industrially in giant volumes in drilling fluids).
Rubidium however does not have any synthetic uses I know of.

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37. processchemist on October 27, 2009 6:46 AM writes...

In my experience every time I scaled up a synthesis involving Cs salts at the end of development Cs was replaced by Na, K, Li.

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38. Tomato on October 27, 2009 8:13 AM writes...

"Has anyone in an organic chemistry lab ever used hafnium or tantalum? Didn't think so."

Maybe my experience has been fairly organometallic up to this point, but in exploring reductive coupling methodology, you got yer Ni, Co, Zr, and Ti, but plenty of us venture into the dark d-block of Nb, Ta, Hf, W, Mn, and Mo.

see: Utimoto, Buchwald, Sato, etc...

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39. Clark on October 27, 2009 9:16 AM writes...

Just a minute or two ago I was carrying around 15kg of Ge, which had about one drop of Ga mixed in with it. It is interesting to think that for every element that you say to yourself "I can't imagine why I would ever use that" there is someone else out there who uses it every single day.

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40. anon on October 27, 2009 10:12 AM writes...

not that I have ever used it in organic synthesis (or done any org. synth...) its rather probable that the reputation of SmI2 of not working is down to people failing to prepare/handle the SmI2 properly. One of my labmates prepared it once and it is really quite sensitive. Stuff from Aldrich is probably all crap.

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41. chemist on October 27, 2009 10:39 AM writes...

Years ago, I and colleagues were kicking around ideas. "RLi, RMgX, ... Why not RBeX and R2Be?" It was such a good idea that it had already been investigated by Gilman in the 1920s. E.g., Gilman and Schulze, J Am Chem Soc, 1927, 49, 2904 and others. (They are less reactive than RMgBr and don't form as easily.)

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42. cookingwithsolvents on October 27, 2009 10:43 AM writes...

RE 15, 25 @ metathesis.

Some of the best catalysts are W (very stable to self-decomposition, e.g. DOI: 10.1021/om800877q ) and the original catalysts were Ta. The synthesis of the W catalysts is a little tougher than the Mo. Ta catalysts have historically shown high propensity for deactivation pathways.

I can't comment on the Fe,Ru,Os group much except that I'm sure Fe and Os been examined pretty thoroughly.

I'm actually surprised that there aren't more metals that do metathesis (Re does alkyne). Then again, there are lots of other options for that M-C pi bond to do (the above mentioned + Legzdins, Mindiola-type C-H activation work). For all we know some Tc compound is the best catalyst and that's too bad for us, eh? :)

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43. retread on October 27, 2009 12:26 PM writes...

Tak, & CookingWithSolvents: Thanks for the responses. Sometimes reading chemistry is like reading math where a set of bizarre postulates (Ruthenium, complex conjugation rather than simple multiplication for the inner product) is shown to produce the desired effect (metathesis, Hermitian operators producing real eigenvalues) with no idea of how many false starts there were and how the successful ones came to be. It's good to see that all the transitionals were studied and that we're just hearing about the ones that worked.

We're just starting to plot spherical harmonics (s, p, d, f orbitals etc.) in the QM course, and when I understand them enough, I might also understand why some of the transition metals work in the reaction and why some don't. Thanks again.

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44. Amother Kevin on October 27, 2009 7:56 PM writes...

Nobody's mentioned gadolinium, yet?

Well, I guess Derek did, when he mentioned wonky NMR shift agents. That's what it turned up for in my lab.

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45. Jordan on October 28, 2009 8:40 AM writes...

+1 for Sc(OTf)3 as a nice water-tolerant Lewis acid. I have used it to catalyze ring-opening reactions.

Cs2(CO3) is somewhat common in supramolecular chemistry for closing macrocyles with oligo(ethylene glycol) chains (template effect).

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46. crazyscot on October 28, 2009 5:27 PM writes...

I was only a chemist as far as my first year at college, but got to use a little cerium sulphate in my high-school chem project. Belousov's reaction is truly awesome to behold, my immediate response was "how in the world is this even possible" :)

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47. Anonymous on October 31, 2009 11:37 AM writes...

Another vote for scandium triflate as a lewis acid. It's nice.

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48. sjb on November 8, 2009 11:35 AM writes...

Just to follow up on Tomato's post (38), yes, I have used tantalum (not very successfully mind) to do work similar to try some work similar to http://dx.doi.org/10.1021/ja00255a073 .

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49. mes on November 19, 2009 5:50 PM writes...

As a biochemist not a "real chemist", I have little reason or opportunity to use most of the elements beyond the second row other than in lab buffers or physiological salts. However, among rarer elements not used synthetically, OsO4 for for staining in electron microscopy, arsenic as someone pointed out in cacodylate buffers when methylating DNA (and don't want the buffer to sop up the methylating agent), and most interestingly, europium salts in phosphorimaging to detect radioactivity in gels without using X-ray film.

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50. Jas on February 15, 2011 5:28 AM writes...

It's funny, but in my life as a semiconductor jerk, I've found the ones you list off as difficult to find uses for the most useful of all.

Beryllium oxide is a great ceramic insulator for power electronics, especially since you can get it to have the same coefficient of thermal expansion as metal or glass.

Scandium, yttrium, lanthanum: dope a glass fibre with them, you've got yourself an optical amplifier!

Gallium is great for low-temperature solder, and also for whole swathes of III-V semiconductors (gallium nitride for blue LEDs, gallium arsenide for infra-red, add some aluminium for red). Bonus points if you sue your employer over the patent rights!

Germanium is where solid state electronics all began, of course, and it's also useful for infra-red optics. Silicon-germanium is probably the key enabling technology for 3G wireless chipsets, too. You can make really, really fast FETs that way.

Indium is used as thermal jointing compound for semiconductors that get really hot (say, laser diodes) and is also used in optoelectronics (blue laserdiodes are made of carefully-controlled epitaxially grown indium gallium nitride).

Krypton is used in ion lasers, to make red lines, which was more impressive before GaAlAs laserdiodes came along and did it hundreds of times more efficiently and without all that tedious and dangerous messing around with three-phase power supplies and fancy glassware. (Made of beryllia.)

Yttrium is another one of those elements used in solid-state lasers, and puts the Y in YAG. If you have a green laser pointer, you use yttrium. (And it's pumped by a GaAs or GaAlAs laserdiode, too.)

Strontium's used in a lot of magnesium alloys, to improve creep properties under load. Magnesium car and motorcycle parts have strontium in them. If you're rich enough to drive a BMW, then maybe you use it after all.

Cadmium's persona non grata these days, but used to be used in a lot of electronics as an anti-whisker plating, as well as being used in NiCd battery chemistries.

Selenium used to be used in camera tubes and even in photocopier drums, but organic photoconductors are more popular these days and last better.

Hafnium, again, is used in lasers, and tantalum is just about everywhere in modern electronic devices- it makes really great electrolytic capacitors with extremely low inductance and equivalent series resistance, so you can use it to smooth out the staccato power drain of your digital circuits and stop 'em crowbarring each other.

You'd be surprised just how much chemistry is involved in pushing electrons around in a somewhat organized way...

And, of course, if you need really, really bright light, the EEs in the house reach for that xenon strobe tube.

Permalink to Comment

51. Jas on February 15, 2011 5:33 AM writes...

Oh! I forgot samarium- used in those supermagnets that are cropping up everywhere.

Hafnium, I almost forgot, is the secret-sauce in low-K dielectrics that semiconductor manufacturers are using to shrink their teeny tiny FETs ever smaller, too. Expect prices to rise as Intel and AMD absorb ever more of it.

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Speaking at Northeastern