Sciencemadness Discussion Board

Any interesting uses for dimethylglyoxime?

Metacelsus - 21-3-2019 at 00:05

Due to a shipping mistake, I got some dimethylglyoxime for free. I know it's used to form coordination complexes. Is there anything else particularly interesting I can do with it?

Herr Haber - 21-3-2019 at 03:51

Pd recovery !

DraconicAcid - 21-3-2019 at 09:42

Sorry- I can't parse what you've written. You want something particularly interesting, but *not* coordination complexes? it's like you're asking for an example of something that is simultaneously a tree and not tree......

fusso - 21-3-2019 at 09:52

I think he was asking for uses for H2Dmg other than as a ligand.

[Edited on 190321 by fusso]

DraconicAcid - 21-3-2019 at 11:58

Quote: Originally posted by fusso  
I think he was asking for uses for H2Dmg other than as a ligand.


Yes, but he also said "interesting uses", which is contradictory.

(Me? Biased towards coordination chemistry? Never!)

Metacelsus - 21-3-2019 at 12:00

Yes, I'm familiar with its use as a ligand but I wanted to see if there were any other uses for it. I didn't want this thread to just be suggesting a bunch of coordination complexes to make.

For example, acetylacetone is a common ligand but it can also be used for synthesis of pyrimidines.

UC235 - 21-3-2019 at 17:40

If you have a lot of it, you could try the excruciatingly slow distillation of diacetyl from a strongly acidified (HCl) solution of the stuff. I recommend a vigreux and extremely slow takeoff. It's a yellow liquid and is the pure essence of movie popcorn butter flavor. Even if you don't get it pure, it's super strong scented.

Oximes are really slow to hydrolyze though, compared to azines. The stillpot residue also can be concentrated to produce hydroxylamine salts.

[Edited on 22-3-2019 by UC235]

Pumukli - 22-3-2019 at 11:46

Dear UC235,

Could you elaborate a bit on why did you suggest using HCl as an acid for the distillation? Could people use say 60% H2SO4 instead? Does HCl has any special advantage in this reaction?

Btw, when I was looking into this particular compound (diacetyl) years ago I learned that it is a nasty carcinogene with a unique mechanism of action and cause a unique nasal/laryngeal cancer in workers who roast popcorn 24/7 in an ill-ventillated boot.

Probably nothing to worry about in the above experiment but interesting to know that a seemingly inoccus (and pleasant smelling) food additive (is it ?) can do such things.

clearly_not_atara - 22-3-2019 at 16:53

If you convert both oximes to the iminyl tosylates, reduction with zinc amalgam might produce a short-lived 3,4-dimethyl-1,2-diazetine, which will spontaneously release N2, and, if I'm guessing right, a photon.

It might generate a 7-membered ring with SOCl2? Doubt it'll be stable but maybe the decomposition is interesting? I see the possibility of a 2,1,3-oxadiazole, but these weird things are usually only stable when attached to benzene.

(These are random guesses, perform with caution.)

See also:

http://nopr.niscair.res.in/bitstream/123456789/22543/1/IJCB%2039B(7)%20551-553.pdf

[Edited on 23-3-2019 by clearly_not_atara]

UC235 - 22-3-2019 at 18:16

Quote: Originally posted by Pumukli  
Dear UC235,

Could you elaborate a bit on why did you suggest using HCl as an acid for the distillation? Could people use say 60% H2SO4 instead? Does HCl has any special advantage in this reaction?

Btw, when I was looking into this particular compound (diacetyl) years ago I learned that it is a nasty carcinogene with a unique mechanism of action and cause a unique nasal/laryngeal cancer in workers who roast popcorn 24/7 in an ill-ventillated boot.

Probably nothing to worry about in the above experiment but interesting to know that a seemingly inoccus (and pleasant smelling) food additive (is it ?) can do such things.


I'm not sure it matters. Unlikely. There was already HCl in the reaction mix when I made the diacetyl monoxime that I acidified further and distilled diacetyl from. Dimethylglyoxime should behave similarly with excess acid.

Boffis - 24-3-2019 at 03:53

@metacelsus, dimethylglyoxime can be cyclotized to dimethylfurazan and then oxidized to the corresponding dicarboxylic acid with alkaline permanganate. I seem to recall that gentle oxidation converts it to the corresponding dimethylfuroxan. I have some reference to these procedures somewhere which I will dig out if you are interested.

PirateDocBrown - 24-3-2019 at 17:02

It is an indicator for the presence of nickel in solution.

It forms a characteristic strawberry red complex.

CharlieA - 25-3-2019 at 16:17

So, how much do you have? I mean, could you sell a couple of grams and send it to the US?Charlie