Road to Making PhB(Epin) - The Most Useful Chemical of the Year?
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- čas přidán 26. 08. 2022
- Small mistake at 3:19 - misspoke, the number on the screen is correct!
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In this video I'm making mercury(ii)chloride, epin (3,4-diethyl-hexane-3,4-diol) and trimethyl borate to continue with in my next video to make phenyl boronic acid, phenyl boronic acid epin ester and a mystery molecule to test the reagent. - Věda a technologie
![Making Dibenzo[a,e]cyclooctene - an Emerging Ligand?](/img/n.gif)
Don’t drop your stir bar in like that, you’ll break a flask one day. Slide it in from an angle. Awesome video!
I seriously think he does that to trigger us😜
You actually need 5 A molecular sieves to remove MeOH effectively, but I would simply get some dry ice and freeze the borate out of liquid MeOH. Don’t forget to put 3 A mol. sieves to the brew, since dry ice always has some water on the surface and you really don’t want any left when you collect solid TMB. Good luck!
This is actually a very insightful video, especially with the showcasing of MeOH and B(OMe)3 separation, not always fun that reported procedures don’t work 🙃
I can't tell you how many chemical patents I've found that don't work. It's incredibly frustrating.
Fantastic project! I had the same idea many years ago, but never got around to trying it out. I wasn't aware of Epin having the superior properties you mention, so I'm doubly glad someone's trying it and publishing it for all to know!
Sounds cool, can't wait to see the product!
Perhaps another more expensive way to synthesize Epin is to do a Grignard reaction with EtMgBr on Diethyl oxalate, but I'm not sure.
A grignard reaction with 4 equivalents of ethyl magnesium bromide reacting with diethyl oxalate to make Epin could avoid using Mercury salts maybe...
yes I thought about the same when I saw the preview
Huge amount of work. Well done.
I guess freezing it below -34°C (melting point of trimethylborate) would be an option, if you have a freezer capable of those temperatures since the melting point of methanol is at -97,6°C.
Dry ice could be the solution then.
@@user255 yeah good idea, didn't think of that
Cant wait to see the following videos.
SO MUCH CHEMISTRY IN ONE VIDEO! NICE WORK!!!
Thanks for your effort and Nice vídeo , I'm not an organic chemist but just one advice cap very well the trimethylborate; unfortunally I did n't and it hydrolized with the air, so the neck of the bottle was filled with crystals of boric acid (it was n't extra pure was the azeotrope mix )
so now you're starting to make proper videos imho. If you're interested in my opinion, you should be careful not to become "NileRed2". Find you niche in the specialized chemistry you're in - and exactly that you seem to be doing here. I would prefer some of the explanations going into more detail, for example the mechanisms behind the reactions, possible alternatives etc. pp.; you could basically become the "NileRed for real chemists", if you will, more focussed on the chemistry itself.
Completely agree with this! I love the more advanced and specialized nature of these videos!
I miss Doug's Lab -- he had some good explanations of mechanism and the videos didn't feel rushed. Some parts you need to speed up but I think at times a slower pace makes it more enjoyable for nonchemists like me but then I'm biased
@@joeyhinds6216 Doug's Lab was amazing and a very good example for how to do it "right" - he built in so many little practical tips or interesting side facts, I genuinely improved some of my own abilities and methods in the lab because of those. Thats what I would love to see this channel evolve into; a bunch of practical tips that at least sometimes can actually help you with the stuff you're doing in the lab yourself.
Deffo agree
Totally agree
This is really useful content!
Stay safe and I hope you can figure out how to isolate your trimethyl borate!
A Suzuki coupling cycle would be nice at the start where you explain for what these are used.
I like your sponsor bc YOU are brilliant! And I look forward to seeing your next video. I just know you can do it! ☺️
Okay I am very interested in the pure trimethylborate as I want to make this too!
"don't you love it when your mercury containing experiment wants to party?" sentences that would make my chemistry teacher spontanously combust also
Hello your channel is very good thanks love for organic chemistry
Try some boron tribromide , that seems to be the easiest route for isolating the pure borate .
It can be a PITA to get so making it yourself is probably going to be your most expedient option .
I've never found a non industrial synth for BBr3, and I've looked a good bit. How's it done on lab scale?
This is one of the best *reaction* videos on CZcams. 😃 👍
Good. I really like how you're choosing to rely on distillation over column chromatography. Do you mind making a tutorial video on fractional distillation?
Try to salt out the azeotrope with CaCl2 or ZnCl2, they are both soluble in methanol. ZnCl2 and LiCl work 100%
Very good video
Can't you make the Epin with a grignard reaction between dimethyl oxalate and an Ethyl magnesium halide?
I would call that a small stir bar.
conc. HCl(aq) should mix with methanol and might seperate from the trimethylborane.
A brave undertaking you have started! May the force of free electrons be with you. ⚗️
An alternative way to Epin is probably from oxalate diester with excess ethyl grignard
Can't you use sodium to convert methanol to sodium methoxide?
where do I download literature?
maybe you could try leverage their different melting points? Freeze the mixture using liquid nitrogen(if you have access to that) and then thaw in an acetone / dry ice bath. That should leave the solid trimethyl borate behind. (In theory,... I've never tried this specific purification)
That is not going to work, when you thaw the mixture the compound with the higher melting point will dissolve in the compound with the lower melting in point.
The method with the 4A sieves works fine right?
@@derktewinkel that's of course true. I think this procedure is only useful to enrich the compound of interest past the azeotrope to a certain extent. But even that can help, like how people prepare strong ethanol solutions by freezing. Correct me if I'm wrong though.
Also yeah. Just add a whole bunch of molsieves and be done with it xD
heloo it s a offtopic quiestion:than you
thers a way to reduce a diol to OH group?
ex converting hydrochinon to fenol?
There are ways to dexygenate alcohols, such as Barton-Mccrombie reaction, but they are not selective and won't work on phenols, only on aliphatic diols.
Please make vdo for making B2(Epin)2
The molecule looks like a bobblehead figurine XD
what is the risk of the organic mercury compounds? which ones are at risk of being formed? isn't magnesium used in place of aluminum for pinacol, and is it because of this risk?
Mercury is a soft metal, so it complexes with the thiol and tioether groups in proteins, altering their conformation and interferring with their functions.
Also, C-Hg bonds are very weak, and they readily break homolythically to form alkyl radicals.
At which pressure are you distilling? a mbar information would be much appreciated ;)
Approx 3 mbar
Good job yes using HgCl2 is scarry. A precusors for other drugs? Interesting.
Why dont you try triethylborate instead of the methylester if it is easier to purefy?
Triethylborate is a nightmare of ester synthesis, it boils higher than both water and ethanol
Shouldn't it be possible to make the diol via grignard?
yes it is
Your work is greatly appreciated, sir. Chemistry CZcamsrs that show how to make useful and hard to procure reagents are very helpful to the community. Not like Nilered's how to turn wood clear type videos. It's cool but not really applicable.
You can react the methanol with Na
The mercury nitrate must not be heated too high, otherwise the resulting oxide will decompose further into highly toxic mercury vapor and oxygen!
Additions should be made through a second neck of the flask, never through the condenser or any other attachment...
It hurts my eyes when you're throwing the steering bar into the installed flask :)
Wow, I only knew the Mg/NH4Cl/HgCl2 pinacol coupling, but this is interesting, because Aluminium is a cheaper alternative and the purification of B(OMe)3 was also interesting and useful, because I've never seen a single article or video how to break the azeotrope. I find all of your videos really good, because they are a source of education imo. I'm going to 11th grade and learning chemistry along the way and videos like this can help a lot, so thank you!
The purification of trimethyl borate could be performed with just salting out
Cool
Bro if you want to remove methanol, just add 3A or 4A molecular sieves. They suck methanol
Damn just after I said that, you did the exact same thing. Although, I guess at scale, you can do pervaporation to separate those.
10:26 why is it that the trimethylborate molecule looks so much like the symbol from the flag of the isle of man?? 🤣
Mercury (II) chloride and organomercury side products 😋
Ph-B(epin), more like Ph-B(epic).
Oof, a synthesis that starts with mercury catalysis is a big nono
All I see is Stick figures falling and Space invaders.
If you were using the mercury just for the amalgam, why go through all the trouble of making HgCl2? You can use the mercury nitrate directly - or even elemental mercury directly. The steps of making the chloride are simply unnecessary.
That is right. I did it because I simply wanted to follow the procedure exactly.
@@Chemiolis Fair enough, just wondered! I appreciate your reply and your videos - keep going!
Molecular seives 6 A will absorb Methanol.
thats what i fart
🏳⚧🏳⚧🏳⚧🏳⚧
figgin epin :XDDDD
Mmmmmm