Chemiolis - 2024-02-15
In this video I make a new type of reducing agent: Hydrosilatrane 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 Don't conduct any chemical reactions without proper and professional safety analysis and risk management. Measures taken can be invisible, not filmed, not properly visible on camera or misjudged by the viewer due to setup or video construction. Always conduct own appropriate measures regardless of video setup.
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?
Loved the in depth discussion for the last mechanism on this one. The mark of a true organic chemist.
Sodium cyanoborohydride has been pretty quiet since this reductant dropped
It was reduced to silence
@user-yb5cn3np5q lolololol
Si ❕️ ❲ yes in spanish, also happens to be silicon ▪︎‿▪︎ ❳
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
This video was incredibly cool. Group 13/14 elements are very powerful and understudied as catalysts
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
I am so insanely jealous of your glassware, your beautifully stocked lab, and your knowledge. So very fucking jealous.
Ooooh nice and fluffy silicon oxides at the end! Just don't breath it in.
Using mercury to react the aluminum seems like the spiciest way to do this reaction, although probably also the easiest.
Cool vid mate! Well done!
I don't understand chemistry but I love learning things I don't know.
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
Holy shit this took so much effort this is so good
9:30 not an expert, but I guess the free electron pair on the nitrogen bonds to the empty p orbital in the aluminium as a Lewis acid-base pair and then one by one the three oxygen's on the triethanolamine perform a nucleophilic substitution on the aluminum with three, leaving ethoxy groups left over
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
STAB is super useful though, I always make mine in situ from acetic acid and NaBH4
That's what I was thinking. Is it that hard to make STAB from NaBH4? Videos I watched make it seem quite easy
This is amazing!
Yeah bro very cool i will see this Vid now!
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 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.
Inorganic chemistry - who knows!?
cries in point group symmetry and ligand field theory
Why mercury instead or iodine to remove the passivation oxide layer>?
Damn those three dimensional reagents are fancy
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.
Amazing video. Thnx buddy🎉🎉🎉🎉❤
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 :)
This channel is becoming more and more of a "How to speedrun Pihkal"
?
@@YunxiaoChu you basically make all phenethylamines from pihkal via reduktive amination
Cyanoborohydride is a pain because you need to do purification afterward. Is this easily removable?
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
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?
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?
hydrostannatrane is an even stronger hydrogen donor
does this also reduce aldehydes? the favorable advantage of cyanoborohydride in these reactions is that it doesnt fight against the aldhyde like nabh4 does.
Why not react directly the amine with SiCl3H?
when i want to reduce stuff i use sodiumhydroxide, dimethylsulfone, ascorbic acid and water, because the ascorbic will oxidize when heated and thereby reduce my stuff...
had the same result with that, as with the copperhydroxide catalyzed reduction that took too long and it wasn´t that easy to seperate my stuff from the copper, so stopped doing that and came up with a new method...
this gives very good yields too, with the sodiumhydroxide, dimethylsulfone, ascorbic acid and water reduction...
As an inorganic chemist, I also have no idea how that reaction works.
Does this even reduce Shulgin Styrenes?? IYKYK
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.
Uuuu, sounds good from the getgo
How does the iodine destroy the al2o3 layer ??
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! 🙏🏼🫡
1: Dean Stark traps without valve are such a pain when you realize, that there are reactions creating more than 10 mL of water.
2: To opportunity to play the crazy train gitarre part non stop. And probably get copyright striked 😂
pretty sure triacetoxyborohydride would be easier to synthesize from sodium borohydride
Is organic chemistry at this level that much harder than the organic chemistry at this level?! Good god, I thought I knew P-chem at least decently 😭😭😭
@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