Chemiolis - 2024-02-15
Join the patreon! https://www.patreon.com/chemiolis Procedures followed: Boratrane https://sci-hub.se/10.1016/0022-328X(85)80362-4 https://sci-hub.se/https://doi.org/10.1002/zaac.19522680305 Aluminum ethoxide https://sci-hub.se/https://doi.org/10.1016/0022-1902(62)80106-7 Triethoxysilane https://sci-hub.se/https://doi.org/10.1021/jo01160a017 Hydrosilatrane https://orgsyn.org/demo.aspx?prep=v98p0227 https://sci-hub.se/https://doi.org/10.1002/ejoc.201501599
This video has everything! Dean Stark, multiple diy reagents, mercury, crazy looking molecules, amalgamation, vacuum distillation, impurity, reducing an oxide layer, nitrogen balloon, and even a sweet cameo by sick boilover itself! on a scale of 1 to 10 this one's a 25 bruh!
Can we just appreciate the effort he puts into keeping us on the edge of our seats for 11 minutes with ethoxides? This one's a banger!
Dont. forget a broken graduated cylinder. You're not a chemist if you don't have one of those.
@@nunyabisnass1141 That and a lot more, there's too much to list!
You had me at Dean-Stark.
Lil ball of iodine
But has it Tar?
Sodium cyanoborohydride has been pretty quiet since this reductant dropped
It was reduced to silence
@@Spencergolde You mean, silanes?
@@user-yb5cn3np5q lolololol
Si ❕️ ❲ yes in spanish, also happens to be silicon ▪︎‿▪︎ ❳
Loved the in depth discussion for the last mechanism on this one. The mark of a true organic chemist.
it amazes me every time how much time and effort is spent on every chemiolis video...
very based move of linking the procedures via scihub in the description
Fun fact, reciprocating steam engines use a device like that Dean-Stark trap, but to cause accumulated water to lift a controlled quantity of lube oil into each cylinder.
Always nice to see new and safer reagents come along, looking foward to seeing how it compares to NaBH3CN!
Yes it's "safer" if you ignore how it's made. If you don't it's not safer or greener
@@Bob-lv1xsIn a proper industrial manufacturing setup I actually think this could be made rather cheaply and safely, with minimal wastage
@@mduckernz I have yet to see anything on its EHS or LCA so even if it could be manufactured safely and with minimal waste that still says nothing about the waste itself or what happens once it's actually used, and unless it's perfectly catalytc (see AlCl3 which might as well have to be added stoichiometrically) the waste/product mass ratio is meh
It is nice to see pentacoordinate Silicon compounds get more attention. They are pretty neat
Boratrane can be made by just heating boric acid and triethanolamine neat at 200C for a few hours until the mix solidifies
this is awesome I just today had my organic chem lecture about reductive amination. I feel supremely nerdy for this but i dont remember another time i've been this hype for an upcoming yt video
This video was incredibly cool. Group 13/14 elements are very powerful and understudied as catalysts
Cool vid mate! Well done!
I am so insanely jealous of your glassware, your beautifully stocked lab, and your knowledge. So very fucking jealous.
Holy shit this took so much effort this is so good
This is amazing!
Amazing video. Thnx buddy🎉🎉🎉🎉❤
Using mercury to react the aluminum seems like the spiciest way to do this reaction, although probably also the easiest.
Yeah bro very cool i will see this Vid now!
Hey Chemi! I'm just waiting for you to tell me how does a very chill (Menthol 20x) chemical will do with a very spicy one! Nice video btw! Love your work!
You can eat mint and spicy food, and report back your results. You will likely feel both, they are different receptors.
@@Chemiolis I just wanted to see the results of your top organic ones, since you are the GOAT in making things very extreme and the one who probably can take it like a champ! I tried one time. Mentol in almost freezing water and eating a Habanero. It was very weird and the problem wasn't even in my tongue, it was in my stomach for some reason. Yeah, I could feel both and it was WEIRD! Maybe doing it, mixing in some slurry, adding some carbonation or something that feels like it makes you tongue "tingle" like an electric shock is my end goal if my stomach can take that.
Sounds like you want to put chemiolis through hell
True, and he definitely goes throughenoughof that as is, lol‥…@@otterconnor942
Ooooh nice and fluffy silicon oxides at the end! Just don't breath it in.
Inorganic chemistry - who knows!?
cries in point group symmetry and ligand field theory
Dude cool
Love your videos
Have you thought of using a huber ministat and a jacketed flask for the temperature sensitive stuff?
(Lot of coin but can be done semi-cheap if you get creative)
I plan to use something like that for cooling very exothermic reactions like nitration, but coolers are a bit pricey to justify atm
Could you try making the alkyl variant of this substrate to see if it can do hiyama couplings?
How 'bout you get going on this if he can't and let us know.
Damn those three dimensional reagents are fancy
STAB is super useful though, I always make mine in situ from acetic acid and NaBH4
I came across an interesting molecule you should try synthesizing!
It’s called Iceane, and is an obscure carbon structure that has the same base structure of a mineral found only in meteorites called lonsdaleite which is (theoretically) stronger than typical diamond.
Cyanoborohydride is a pain because you need to do purification afterward. Is this easily removable?
Nice synthesis and structure. Reminds me of pyrrolizidine alkaloids of my PhD. Is this dark background the inside of a hood? I hope it is!😉👍❤
He’s mentioned he works in a hood yeah :)
Why mercury instead or iodine to remove the passivation oxide layer>?
Since you're heating it anyway and just trying to amalgamate the aluminum to increase surface area, can you just substitute the mercury with gallium so you don't have to risk using a toxic metal?
0:33 that alone makes it worth replacing LAH in lab settings at least, if it weren't for cost, same going to the borohydride and such
I don't understand chemistry but I love learning things I don't know.
does this also reduce aldehydes? the favorable advantage of cyanoborohydride in these reactions is that it doesnt fight against the aldhyde like nabh4 does.
You can also find boric acid in the feminine hygiene section.
I get the purpose of iodine but I don’t understand why is it important to use mercury chloride to the solution to create an amalgam. As long as Aluminum is exposed out of the oxide layer, the reaction should follow suit or did miss something?
Can this reduce pseudoephedrine? Asking for a friend
😗
No , you have to use germanium instead , since it is better for doping ...
HI/H3PO4 friend that is the way or I2/Red P
As an inorganic chemist, I also have no idea how that reaction works.
How does the iodine destroy the al2o3 layer ??
Uuuu, sounds good from the getgo
This channel is becoming more and more of a "How to speedrun Pihkal"
hydrostannatrane is an even stronger hydrogen donor
Yes, and also a much stronger poison.
pretty sure triacetoxyborohydride would be easier to synthesize from sodium borohydride
7:18 Couldn't we just used sodium ethoxide would had made sodium chloride instead of HCl. If i most say, some inorganic compounds are special in organic chemistry, opens up more possibility that can take shortcuts to building molecule.
Woah I subbed and a new video dropped?!
Quick , do it again .
Very interesting procedure here. The 1st reduction reaction I learned of that reduces aldehydes and ketones into amines was the Lukehart reduction. Pretty cool to see other avenues like this that work in what seems to be a fairly easy manner. Keep educating Chemiolis! 🙏🏼🫡
JESSE WE HAVE TO COOK
Ketones and esters, Oh my! Ketones and esters, Oh my! Ketones and esters, Oh my! Signed: Dorothy and gang.
I hate it when my silanes turn yellow. I can't stop them from doing it.
Yellow chemistry 🥹💛✨
Reductive amination? Don’t mind if I do…
@B_u_L_i - 2024-02-15
Babe wake up. A new reducing agent just dropped.
@Spencergolde - 2024-02-15
Biggest news since carrot reducing agents dropped
@B_u_L_i - 2024-02-15
@@Spencergolde omg yass, that paper slayed so hard
@Spencergolde - 2024-02-15
@@B_u_L_i Right? And their setup was so far from being optimized. Carrots or other root vegetables could be such a gamechanger in a world where decent reducing agents are so strictly controlled
@07Roux - 2024-02-16
Literally as soon as he woke up. “O….k.? What’s that?”
@GoikOShea - 2024-02-16
OIL RIG