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DraconicAcid
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Triphenylphosphine is a perfectly safe solid that I used as an undergrad. Trimethylphosphine, on the other hand, is much more volatile and toxic, as
is phosphine, methylphosphine, etc.
I had to use nickel tetracarbonyl once. Didn't enjoy it. Would never make it at home.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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JJay
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I could see possibly making it in a professional setting, but as an amatuer? Definitely not.
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benzylchloride1
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One of the more memorable things that I have seen in my years.
[Edited on 4-5-2017 by benzylchloride1]
Amateur NMR spectroscopist
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karlos³
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Is that bis-trifluoromethyl mercury?? 
Where did you get this picture from, certainly not shot yourself don´t you?
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benzylchloride1
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It is indeed bistrifluoromethyl mercury, I took the picture over a year ago. Interestingly, this compound is a light orange solid as can be seen in
the small Nalgene bottle, as opposed to dimethylmercury which is a colorless liquid. The large crystallizing dishes contain mercuric iodide recovered
from years of chemical oxygen demand testing of waste water. Much worse stuff is still lurking on the 5th floor of the building...
Amateur NMR spectroscopist
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Radium212
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Phosgene or chloroacetone. Acetone peroxide, as well.
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j_sum1
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Coloured mercury
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JJay
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I've actually been considering bromoacetaldehyde. I think it will react with lithium diphenylcopper or diphenylzinc to make phenylacetaldehyde in good
yield.
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Texium
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Thread Moved
25-7-2017 at 20:17 |
Loptr
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Quote: Originally posted by JJay  | | I've actually been considering bromoacetaldehyde. I think it will react with lithium diphenylcopper or diphenylzinc to make phenylacetaldehyde in good
yield. |
Which route to the Gilman reagent would you take? This is something I have been thinking about lately, too. Not to phenylacetaldehyde, but
organocuprates in general.
They can be prepared from their corresponding Grignard reagent with copper (I) salts. The counter ion would then be magnesium.
[Edited on 26-7-2017 by Loptr]
"Question everything generally thought to be obvious." - Dieter Rams
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JJay
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I'd probably use phenyllithium and copper (I) chloride. I have wondered how hard it would be to prepare organocuprates from phenylsodium.
I don't think it's a good idea to prepare phenyllithium without inert gas, but a phenyl Grignard can be prepared with a drying tube....
I think phenylacetaldehyde can be made with diphenylmercury too. But I am not going to make that.
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unionised
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I will never make a contribution to this thread consisting of information on chemicals I will, or at least hope to, make.
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Loptr
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| Quote: Originally posted by JJay | I'd probably use phenyllithium and copper (I) chloride. I have wondered how hard it would be to prepare organocuprates from phenylsodium.
I don't think it's a good idea to prepare phenyllithium without inert gas, but a phenyl Grignard can be prepared with a drying tube....
I think phenylacetaldehyde can be made with diphenylmercury too. But I am not going to make that. |
Yeah, forget that one. I think that would be a series of compounds I could add to this thread in good faith; organomercury compounds! I am fine with
mercury salts, just be sure to clean up and recover as much of the salt as possible for reuse, and also to keep it from getting into the environment.
As for the air-sensitivity of lithium reagents, that is exactly why I considered the route from Grignard reagents. I have pretty much everything else
needed to work in an inert environment, except for the gas bottle and one of those drying apparatuses that fits onto the bottle itself.
[Edited on 27-7-2017 by Loptr]
"Question everything generally thought to be obvious." - Dieter Rams
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JJay
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Same here. I need an argon tank.
I do like the Grignard route. I could theoretically whip up a batch of diphenylcopper magnesium bromide right now using materials I have on hand if I
pick up some ether.
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Refinery
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Things I will never do?
In my current setup:
Any reaction that could get out of hand, is too toxic to be handled, has such strong odor it will persist. I'm also not keen on energetics because I
don't have place to play with them, and also things that are highly illegal shall remain untouched for now. Every synthesis I plan, I strongly
consider how I can actually deal with it, does it need any containment, does it pose contamination hazard, how do I manage the waste, what equipment I
need, etc.
In any given time:
I wish I could do every chemical reaction there is. The more exotic substance, more the merrier. Blast-proof, biolab level fume hood with ability to
remotely control many processes would be a nice one for a start.
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Eddie Current
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I am mostly interested in the reaction mechanisms & older chemistry techniques, and can study them without illegal drugs & poisons or
designated explosives.
As for chemicals, I will never go near HF or HgC2H6 regardless of the inducement and there's a few other substances that I would avoid in the hobby
setting.
Otherwise, let's do some chemistry.
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Metacelsus
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| Quote: Originally posted by JJay | I'd probably use phenyllithium and copper (I) chloride. I have wondered how hard it would be to prepare organocuprates from phenylsodium.
I don't think it's a good idea to prepare phenyllithium without inert gas, but a phenyl Grignard can be prepared with a drying tube....
I think phenylacetaldehyde can be made with diphenylmercury too. But I am not going to make that. |
Fun story time. Back in undergrad I worked in an organic synthesis lab. I needed to use some phenylsilane reagent (I believe it was triphenylsilane
but I'm not completely sure). It turned out the lab had an old bottle of the stuff, way at the back of one of the storage cabinets. You know, back
where nothing has been touched since 1975.
The cap was pretty crusty-looking, so after opening it I took a GC-MS to check the quality. The main component was there as expected, and there were
also lots of siloxane oxidation products coming at later retention times. Maybe I could distill it to clean it up, I thought.
But I also noticed a strange minor peak coming just before the retention time of the main compound. The m/z read 356. I did a spectrum database
search, and guess what: diphenylmercury! It was probably an impurity from the synthesis.
Needless to say, I successfully convinced my PI to buy a new bottle.
[Edited on 2020-7-6 by Metacelsus]
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