Student at office door: "John, a compound is crystallizing in my NMR tube of this extract!"

"Cool! Add some DMSO though and we will check that later"

"Its in DMSO"

The air conditioning was on. I leave this as am exercise to the reader. A lesson was learned.

April 09, 2026 - 15:32 UTC

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Been here, and I even managed to mount it.
bsky.app/profile/ntumanovxray.bsky.social/post/3mbz6ogkcbc2z
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I have isolated more triphenylphosphine oxide (from reactions with o triphenylphosphine....it carried through i guess) than I would care to contemplate.
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I get the lesson, but why'd you suggest adding dmso in the first place?

Im not through my coffee yet 😅
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I don't remember much from my undergrad lectures at this point. But I do remember - (basically) everything dissolves in DMSO.
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Complex natural product extracts...want it all soluble for the nmr. Often complex solubilities, and yeah as our colleague notes...DMSO dissolves almost everything. Especially when you dont know what you have.
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DMSO is our season clock
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personally, I always enjoyed the intimate moments I spent closely embracing the t-BuOH bottle...
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Or the time spent holding it in the rotovap bath
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There is nothing more sensual than shoving ampules of dmso down your pants...wait, you people dont do that?

But yeah melting the tbuOH...honestly I worked hard on dolvent alternatives for Sharpless CuAAC (9:1 THF: H2O is my fave) because I hate tBuOH.
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reminds me of the time i tried to vacuum filter a large quantity of cyclohexane ☃️
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Had this happen once at very large scale. A CRO in a cold climate stored barrels of DMSO outdoors, needless to say the start of my batch that was slatted to run in said solvent was delayed for a few days.
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I saw the opposite problem when I was doing a summer school thing - undergrad kept finding impurities in her chemistry and at least part of it was because it was run in THF which was stored on the loading dock in DC summer (close to 40C).
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“I’ve seen some things…”

When your compound actually crystallizes from DMSO in the NMR tube (yeah that’s happened - more than a few times)
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