Making Hydrosilatrane: A Better Reductant?

[@B_u_L_i]

Babe wake up. A new reducing agent just dropped.

[@Spencergolde]

Biggest news since carrot reducing agents dropped

[@B_u_L_i]

@@Spencergolde omg yass, that paper slayed so hard

[@Spencergolde]

@@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]

Literally as soon as he woke up. “O….k.? What’s that?”

[@GoikOShea]

OIL RIG

[@rustymustard7798]

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!

[@nunyabisnass1141]

Dont. forget a broken graduated cylinder. You're not a chemist if you don't have one of those.

[@rustymustard7798]

@@nunyabisnass1141 That and a lot more, there's too much to list!

[@andrewjuby6339]

You had me at Dean-Stark.

[@baha17222]

Lil ball of iodine

[@again5t.your53lf6]

But has it Tar?

[@brandonbennett3082]

Loved the in depth discussion for the last mechanism on this one. The mark of a true organic chemist.

[@김드림_Drim_Kim]

Sodium cyanoborohydride has been pretty quiet since this reductant dropped

[@Spencergolde]

It was reduced to silence

[@Andy_M.S.c]

@user-yb5cn3np5q lolololol

[@ShortFuseMan]

Si _❕️_ *❲* yes in spanish, also happens to be silicon ▪︎‿▪︎ *❳*

[@sorooshsaghebi9465]

it amazes me every time how much time and effort is spent on every chemiolis video...

[@swaree]

very based move of linking the procedures via scihub in the description

[@jimsvideos7201]

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.

[@chemistrycapital]

Always nice to see new and safer reagents come along, looking foward to seeing how it compares to NaBH3CN!

[@Bob-lv1xs]

Yes it's "safer" if you ignore how it's made. If you don't it's not safer or greener

[@mduckernz]

@@Bob-lv1xsIn a proper industrial manufacturing setup I actually think this could be made rather cheaply and safely, with minimal wastage

[@Andy_M.S.c]

@@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

[@Zenzicubic]

Boratrane can be made by just heating boric acid and triethanolamine neat at 200C for a few hours until the mix solidifies

[@penteractgaming]

It is nice to see pentacoordinate Silicon compounds get more attention. They are pretty neat

[@chir0pter]

This video was incredibly cool. Group 13/14 elements are very powerful and understudied as catalysts

[@dansamarco1610]

I am so insanely jealous of your glassware, your beautifully stocked lab, and your knowledge. So very fucking jealous.

[@Casbury_]

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

[@bryce4359]

Can this reduce pseudoephedrine? Asking for a friend

[@kjpmi]

😗

[@kaboom4679]

No , you have to use germanium instead , since it is better for doping ...

[@t0lek511]

HI/H3PO4 friend that is the way or I2/Red P

[@Drjtherrien]

Ooooh nice and fluffy silicon oxides at the end! Just don't breath it in.

[@Andy_M.S.c]

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

[@Petemate69]

Why mercury instead or iodine to remove the passivation oxide layer>?

[@AManChoosesASlaveObeys]

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!

[@Chemiolis]

You can eat mint and spicy food, and report back your results. You will likely feel both, they are different receptors.

[@AManChoosesASlaveObeys]

@@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.

[@otterconnor942]

Sounds like you want to put chemiolis through hell

[@ShortFuseMan]

​True, and he definitely goes throughenoughof that as is, lol‥…@@otterconnor942

[@andrewjin6618]

Could you try making the alkyl variant of this substrate to see if it can do hiyama couplings?

[@pharmdiesel]

How 'bout you get going on this if he can't and let us know.

[@DRTDC90]

Cool vid mate! Well done!

[@clarfonthey]

Using mercury to react the aluminum seems like the spiciest way to do this reaction, although probably also the easiest.

[@vmi3_]

Inorganic chemistry - who knows!?

[@Andy_M.S.c]

_cries in point group symmetry and ligand field theory_

[@stinooke]

STAB is super useful though, I always make mine in situ from acetic acid and NaBH4

[@LordBrainz]

That's what I was thinking. Is it that hard to make STAB from NaBH4? Videos I watched make it seem quite easy

[@peteragardi1175]

Amazing video. Thnx buddy🎉🎉🎉🎉❤

[@Lukesab3r]

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)

[@Chemiolis]

I plan to use something like that for cooling very exothermic reactions like nitration, but coolers are a bit pricey to justify atm

[@DudeManDude-ot5fv]

I don't understand chemistry but I love learning things I don't know.

[@captainchicky3744]

Holy shit this took so much effort this is so good

[@THYZOID]

Damn those three dimensional reagents are fancy

[@n.m.sh.8706]

Why not react directly the amine with SiCl3H?

[@Relatablename]

This is amazing!

[@SixTough]

Cyanoborohydride is a pain because you need to do purification afterward. Is this easily removable?

[@MrYellowOffical]

Yeah bro very cool i will see this Vid now!

[@TheDexCrafter]

How does the iodine destroy the al2o3 layer ??

[@joalsoal1645]

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.

[@VietCong-ln1jf]

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!😉👍❤

[@Girvo747]

He’s mentioned he works in a hood yeah :)

[@neffix6976]

This channel is becoming more and more of a "How to speedrun Pihkal"

[@YunxiaoChu]

?

[@neffix6976]

@@YunxiaoChu you basically make all phenethylamines from pihkal via reduktive amination

[@brandonross6083]

Does this even reduce Shulgin Styrenes?? IYKYK

[@nunyabisnass1141]

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?

[@KilgoreTroutAsf]

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

[@bsharahdaoud5285]

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?

[@Mp-jw1qg]

does this also reduce aldehydes? the favorable advantage of cyanoborohydride in these reactions is that it doesnt fight against the aldhyde like nabh4 does.

[@evosticks]

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.

[@patrickthomaskuessner5966]

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...

[@patrickthomaskuessner5966]

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...

[@patrickthomaskuessner5966]

this gives very good yields too, with the sodiumhydroxide, dimethylsulfone, ascorbic acid and water reduction...

[@KrashFries]

make lithium alumatrane hydride next

[@Death-uo9lc]

pretty sure triacetoxyborohydride would be easier to synthesize from sodium borohydride

[@leichenkocher]

Uuuu, sounds good from the getgo

[@andrews.4780]

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! 🙏🏼🫡

[@moisttowelette5353]

As an inorganic chemist, I also have no idea how that reaction works.

[@cezarcatalin1406]

hydrostannatrane is an even stronger hydrogen donor

[@adrianhenle]

Yes, and also a *much* stronger poison.

[@Y_sol]

I hate it when my silanes turn yellow. I can't stop them from doing it.

[@Litepaw]

Yellow chemistry 🥹💛✨

[@Sniperboy5551]

Reductive amination? Don’t mind if I do…

[@Felixkeeg]

Neat, but realistically, I don't see this replacing traditional reducing agents. Borohydrides are just so cheap, versatile and easy to tune. Instead of buying cyanoborohydride, I'd just add 1 equiv of NaCN to my reaction and it works just as well.

[@DonnyHooterHoot]

Ketones and esters, Oh my! Ketones and esters, Oh my! Ketones and esters, Oh my! Signed: Dorothy and gang.

[@loiman4179]

JESSE WE HAVE TO COOK

[@Some_Beach]

Woah I subbed and a new video dropped?!

[@kaboom4679]

Quick , do it again .

[@GodlikeIridium]

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 😂

[@neohavic6012]

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* 😭😭😭

[@Lysergide]

Hm maybe I could make this one: “First add toluene” - good I got that “Then boric acid” - cool I have a kilo of that, so far so good “Then triethanolamine” - shit…

[@decepticonne]

b but the reaction mechanism 😢

[@firenation8406]

This is Tybut Tubytu/ naddrganian burzanu / darbyt darbyton

[@Allyloxycarbonyl]

please don`t say Aluminum! it`s ALUMINIUM! ... the Americans are too lazy to say it correctly ... you are European, stay professional :D ... always striggers me when I see bottles of chemicals at work, that are produced in the US and the label says "aluminum" :/

[@davidshelly9142]

Both are acceptable by the scientific community, but Aluminium isn't a European thing, its really just a commonwealth thing

[@kpunkt98]

In German it's also Aluminium.

[@Allyloxycarbonyl]

@@davidshelly9142 "Aluminium (aluminum in North American English) is a chemical element" ... from Wiki only Americans say Aluminum ... A Scottish once told me that the people in America are too lazy to say that extra syllable :D

[@Correct_Opinion]

language prescriptivists gtfo

[@6alecapristrudel]

Aluminimum

[@LordBrainz]

Spoiler (from that future video): LiAlH4 is still better

[@Johnpao215]

Hahahaha then sell that Hydrosilatrane for $$$$. Easy money!

[@xfxox]

Enough bullshit! We want syntheses of L-SD !

[@derktewinkel]

Silly me, always seeing you as a fellow Dutchy... Only to hear you butcher the pronunciation of aluminium to aluminum. 😢