dawt
Hazard to Self
Posts: 74
Registered: 9-5-2016
Location: EU
Member Is Offline
Mood: fluorescent
|
|
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.
|
|
|
Texium
Administrator
Posts: 4618
Registered: 11-1-2014
Location: Salt Lake City
Member Is Offline
Mood: PhD candidate!
|
|
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.
|
|
|
papaya
National Hazard
Posts: 615
Registered: 4-4-2013
Member Is Offline
Mood: reactive
|
|
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 .
|
|
|
njl
National Hazard
Posts: 609
Registered: 26-11-2019
Location: under the sycamore tree
Member Is Offline
Mood: ambivalent
|
|
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.
Reflux condenser?? I barely know her!
|
|
|
draculic acid69
International Hazard
Posts: 1371
Registered: 2-8-2018
Member Is Offline
|
|
I think caustic soda will break it into sodium methane sulphonate
|
|
|
clearly_not_atara
International Hazard
Posts: 2799
Registered: 3-11-2013
Member Is Offline
Mood: Big
|
|
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
|
|
|
Texium
Administrator
Posts: 4618
Registered: 11-1-2014
Location: Salt Lake City
Member Is Offline
Mood: PhD candidate!
|
|
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.
|
|
|
dawt
Hazard to Self
Posts: 74
Registered: 9-5-2016
Location: EU
Member Is Offline
Mood: fluorescent
|
|
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
|
|
|
clearly_not_atara
International Hazard
Posts: 2799
Registered: 3-11-2013
Member Is Offline
Mood: Big
|
|
| 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.
|
|
|
njl
National Hazard
Posts: 609
Registered: 26-11-2019
Location: under the sycamore tree
Member Is Offline
Mood: ambivalent
|
|
See the Reed reaction for more alkyl/sulfonyl radical reactions!
Reflux condenser?? I barely know her!
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
