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Author: Subject: What to do with dimethyl sulfone (methyl sulfonyl methane, MSM)?
dawt
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[*] posted on 16-4-2021 at 09:02
What to do with dimethyl sulfone (methyl sulfonyl methane, MSM)?


Rummaging through my cabinets I discovered a kilo of dimethyl sulfone that I bought probably 10 years ago, simply because it was so cheap. Totally forgot about it, and googling around a bit I haven't found a paper utilising it for something interesting.

Any cool synths I can use this for, that wouldn't be better served by DMSO or the likes? I can very much use the space it's now occupying in my cupboard, so if you can think of something interesting or whacky to try out with it I'd be happy to give it a shot before tossing it out.




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Texium
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[*] posted on 16-4-2021 at 10:01


Unfortunately it's a pretty useless compound due to its lack of reactivity. There's probably a decent catalytic hydrogenation method that could be used to convert it to DMSO (I looked a bit but couldn't find anything, and I don't have time to do a more in depth search right now), but I don't know how useful that would be considering DMSO is pretty inexpensive and easy to find too, and I know that's not really what you're looking for.

The compound is so cheap because it's a popular quack medical supplement. It's 100% safe and 100% ineffective... At least, for most of the claims that people make about it. It could have some benefits for some very specific conditions, but there hasn't been enough research done on that yet, and it certainly isn't a wonder drug.




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papaya
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[*] posted on 16-4-2021 at 16:21


You can try to convert it into methanesulfonic acid by partial anodic oxidation (electrolysis). I've seen a patent long ago, you can search for it, but what are the uses of that acid I'm not aware. It is also a high temperature chemically resistant solvent if you can find a right purpose .
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[*] posted on 16-4-2021 at 16:41


It is apparently sometimes used to cut street methamphetamine. So... there's that. Texium do you think maybe the organic bits could be oxidized? To yield something more useful, maybe an acid or methanesulfonate ester.



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draculic acid69
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[*] posted on 16-4-2021 at 17:01


I think caustic soda will break it into sodium methane sulphonate
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clearly_not_atara
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[*] posted on 16-4-2021 at 18:24


It's actually quite useful, although few people seem to know why. It can be converted by Birch reduction to methanesulfinic acid. Treatment of this sulfinic acid with some chlorinating agents gives methanesulfonyl chloride, a highly versatile intermediate.
https://pubs.acs.org/doi/abs/10.1021/ja01496a050




[Edited on 04-20-1969 by clearly_not_atara]
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Texium
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[*] posted on 16-4-2021 at 21:23


Do you have proof that this procedure works for dimethyl sulfone? The paper that you link does not test it. They detail it working for decyl sulfone, benzyl sulfone, and a variety of aryl sulfones and mixed ones thereof.



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dawt
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[*] posted on 17-4-2021 at 01:38


Quote: Originally posted by papaya  
You can try to convert it into methanesulfonic acid by partial anodic oxidation (electrolysis). I've seen a patent long ago, you can search for it, but what are the uses of that acid I'm not aware.


Neat! I need some methanesulfonic acid for an intramolecular friedel-crafts acylation of 3-phenylpropanoic acid to 1-indanone, see: https://doi.org/10.1021/jo00327a028

There's a few papers and patents detailing the electrochemical oxidation of dimethyl sulfone, these look especially promising: https://doi.org/10.6060/TCCT.20165912.5345 and https://patents.google.com/patent/RU2554880C1/en




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clearly_not_atara
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[*] posted on 17-4-2021 at 06:49


Quote: Originally posted by Texium (zts16)  
Do you have proof that this procedure works for dimethyl sulfone? The paper that you link does not test it. They detail it working for decyl sulfone, benzyl sulfone, and a variety of aryl sulfones and mixed ones thereof.

Negative. However, given the mechanism, I hardly see what else would happen; MSM is highly tolerant to bases and has a pKa of around 31, so I don't think deprotonation is likely to be a major competitor. Nature does not abhor a methyl radical as badly as a methyl carbocation.




[Edited on 04-20-1969 by clearly_not_atara]
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[*] posted on 17-4-2021 at 09:56


See the Reed reaction for more alkyl/sulfonyl radical reactions!



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