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Author: Subject: Things I Will Never Make
DraconicAcid
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[*] posted on 2-5-2017 at 19:35


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.




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JJay
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[*] posted on 2-5-2017 at 19:38


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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[*] posted on 3-5-2017 at 18:27


One of the more memorable things that I have seen in my years.

[Edited on 4-5-2017 by benzylchloride1]

IMG_0173.jpg - 1.5MB




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karlosĀ³
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[*] posted on 6-5-2017 at 13:09


Is that bis-trifluoromethyl mercury?? :o
Where did you get this picture from, certainly not shot yourself donĀ“t you?
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benzylchloride1
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[*] posted on 6-5-2017 at 20:42


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...



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Radium212
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[*] posted on 25-7-2017 at 04:05


Phosgene or chloroacetone. Acetone peroxide, as well.
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[*] posted on 25-7-2017 at 14:38


Coloured mercury
:P
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JJay
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[*] posted on 25-7-2017 at 16:35


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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25-7-2017 at 20:17
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[*] posted on 26-7-2017 at 10:51


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]




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JJay
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[*] posted on 26-7-2017 at 12:44


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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[*] posted on 27-7-2017 at 04:34


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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[*] posted on 27-7-2017 at 07:55


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]




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JJay
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[*] posted on 27-7-2017 at 09:21


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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