Making Tributyltin Hydride - A Unique Hydrogen Donor
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- Опубликовано: 9 ноя 2022
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In this video I am preparing Tributyltin hydride from tin metal, which is a unique and useful hydrogen donor in organic synthesis. I will be using it in the future for a synthesis where it is a required reagent. 
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wake up babe new chemiolis dropped
I think u forget ur schizophrenia pills
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The tartrate should be vigorously stirred with your reaction mixture for a long time (from ca. 2h to overnight) to fully complex the aluminium. Then a completely clear layer forms and you can extract normally.
I am consistently impressed by the frequency, consistency, and depth of your videos. Love to see them!
Yes, magnificent quality!
I love waking up to new chemistry videos!! Thanks for making my day that much better.
That’s quite weird… You really are so professional in my opinion, but that small chaotic part of you and all that fails kinda make you videos even more interesting
Things not going as expected and failing are the essence of chemistry. 99% of the time you are seeing my first try :), luckily i often manage to get something in the end
We always performed the synthesis of SnCl4 on a watercooled frit. This way the solid tin is seperated from the liquid SnCl4. :)
You may be interested in getting a refractometer - these don't cost a fortune and allow you to characterize substances according to their refractive index. It's perfect for scenarios where you expect to have a single, liquid product. Purity can also be estimated by measuring the deviation from the indices given via literature - these estimates get better if you got a clue about which impurities could be present.
that's cool, I was so spoiled from modern characterization techniques at my university that I always thought it must be hell to have only a refractometer. Because I only used it as an undergrad in the teaching lab and it seemed if you had minor impurities, the refractive index was completely off. But these deviation tables sound interesting!
love your videos, im a chemistry undergraduate so they are super useful plus i can relate to the mishaps in the lab
🤝🏻
Great video, filled me with nostalgia for my grandfather's company that made organo-tin stabilizers for plastics. My dad frequently discussed handing drums of tetrabutyl tin and tin tetrachloride.
I really enjoyed this episode. You make chemistry seem very fun.
Magnificent! Thanks.
Back in the day we all used TBTH as a hydrogen donor in our free-radical reactions.
Because, I think, we were doing lots of ESR we had vacuum lines and dry nitrogen. You might find the latter (but using your Argon suppy) to reduce hydrolysis and oxgen-sensitive reactions.
All with Alwyn Davies at UCL Chemistry.
Dude, thats so cool!!
Great video!
Thanks for sharing
Wow nice video!👍🏻🙌🏻
I really like tin chemistry but I prefer not work with it because of it's bad smell that lasts for days. In addition, alkyl tin compounds are extremely poisonous..
Thanks for sharing
Actually from what I read, Iodine doesn‘t just remove the oxide layer from the magnesium, but more importantly it forms the iodide which actually catalyzes the formation of the grignard. No less, great video!
most of the times you will add it to see the starting point of the reaction as discolouring occurs.
@@Torteufel That is true, although sometimes the iodine is used up before the reaction properly takes off. Anyway point is, its not so much the iodine itself thats catalytic but the iodide.
@@gefulltetaubenbrust2788 True as well. :)
I can smell this video
Yep it’s disgusting 🤢
Could you maybe include some closeups of the reactions when they run? I think reactions are always beautiful to watch ;)
Impressive
Interesting, great.
Cool, cool, cool!
This is so bad ass. I just used Bu3SnH for one of my endo-trig cyclization reaction via radical mechanism with AIBN radical initiator.
Hey, Great Video! Slight mistake at 8:17 The reaction of tetrabutyl tin and tin(iv) chloride is a redistribution reaction not a comproportionation one, theres no change in tin oxidation state.
We had some tributyl tin chloride in my lab in a simple glass vial. Probably one of the most toxic and dangerous things I found during my sweep of old chemicals in my lab.
I've heard that tributyltin chloride isn't too bad (still not great though) and that trimethyl tin chloride is far worse in terms of toxicity and also smell.
That being said, trimethyltin derivatives are far more reactive in stile couplings due to less streric bulk around the tin
@@tomflanagan878 actually it might have been trimethyl tin chloride.
@@spiderdude2099 yeah it's horrible stuff. I have heard that it is very stinky as well as being incredibly toxic. You know it's bad when you google it and the third thing to come up is a study about how toxic it is to aquatic life
@@tomflanagan878 organotin compounds are probably second or third in ranking of toxicity of organometallic compounds. Organomercury compounds are obviously number 1 but tin compounds can be hella nasty
@@spiderdude2099 they actually do have a pretty common use though, they are air and moisture stable, and they are used in Stille couplings, which in general is like a Suzuki coupling, just a little faster and cleaner.
Surely some organoarsenic/organocadmium reagents are worse though, I'm not sure if they are as useful as organotins
I'm curious about how did you crush the LAH pellet into powder. Last time when I weighed the LAH pellet, just a small friction from the spatula iginited the whole bottle of LAH...
Is there a way to prepare tributyltin hydride using hydrogen gas rather than a inorganic hydride?
10:23 REVERSE SEP FUNNEL
REVERSE SEP FUNNEL
Very spectacular syntheis, good job! I just want to ask, what is the exact name of the white sealing that you used in your video? I tried look after as rubber or teflon sealing but I didn't find any similar.
It is called a septum
@@tkkot2862 Thank you, that's it!
I recommend getting a bench top nmr as you can get an idea of purity
That feeling when you end up with a vile of clear liquid! success! 😅
Why did you use the grignard reagent and didn't use n-butyllythium directly to do the transmetalation?
Does your PhD advisor know you're using his chemicals to make these videos?! 😂😂😂🤣🤣🤣
Nothing gets me going like the sweet, smell of Diethyl Ether in the morning :P
(Obligatory comment to boost the video in the algorhtythm.)
Great video! ^-^
Doe je dit allemaal in je schuur?
I’d like to see you react tributyltin hydride with acetylene to make vinyl tributyltin. Then, react it with bromobenzene to make styrene.
that seems like a lot of steps/time/reagent to make a commercially available product
This compound is such a pain to work with, how do you clean all this glass? I ended up just throwing out all of my flash tubes instead of generating that much tin contaminated liquid waste
Yes it is really annoying and tin deposits on the glass. I basically just scrubbed it a lot with some cleaning tools and let it soak in a strong base bath.
@@Chemiolis Base bath always does the trick for me too. Hate the smell.
How to make Cl2o7 chemical solution please
I ❤ your videos. Great work!
3:59 you use 1-chlorobutane to make the gringard reagent butyl-magesiumchloride
I guess (carba)stannatrane is synthesized similarly. Wikipedia lists N((CH2)3MgCl)3 as precursor that somehow would needed to be made first. Any insights?
Also pondering about adding CH2SH groups onto the second carbon atoms beyond the central nitrogen (of stannatrane) to link the molecule to a gold surface making it investigatable via scanning probe microscopy. I fear this makes things probably much much more difficult if not impossible 😕.
Such CH2SH linkers have been added to adamantane. There are papers about SPM imaging of the deposited adamantane molecules. Specific example: "Tailoring electronic states of a single molecule using adamantane-based molecular tripods" by Satoshi Katano et al (2013)
I found there is a synthesis pathway for attaching linkers onto brominated adamantane in
"Rigid Molecular Tripod with Adamantane Framework and Thiol Legs. Synthesis and Observation of an Ordered Monolayer on Au(111)" by Toshikazu Kitagawa et al (2005)
It's a good HAT reagent
I am pretty inexperienced with chemistry, but couldn't you also gain confidence that you have tributyltin hydride by measuring melting point and density? If density, MP and BP all match that of TBTH, you should feel pretty confident.
What is better is to put the tin into an alumina boat.
Is this the most toxic compound you’ve made?
Arsenic(III)chloride is more toxic. This has pretty much the same toxicity as triphenylarsine (oral).
Why, though?
A ceramic combustion boat would retain the molten tin.
2:04 That wouldn't have happened if a porcelain boat was used for placing the tin in the tube.
Can't imagine what would have happened if instead of the reaction tube (= my recommendation on the previous video 😉) the less heat resistent condenser was used here again...
Tin surface area🎉😂 what no tin microspheres
Don't try this one at home kids.