Making Triphenylarsine with Arsenic Metal
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- čas přidán 29. 10. 2022
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In this video I am having my first attempt at organoarsenic chemistry. I bought an ampoule of arsenic metal which I chlorinated to arsenic(III)chloride using chlorine produced from pool chlorine tablets. I then used this to synthesize triphenylarsine.
I added captions for this video!
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Procedure for triphenylarsine:
www.orgsyn.org/demo.aspx?prep=... - Věda a technologie
I still can't believe you were willing to do organoarsenic chemistry 💀
Should've _fukinone_ you'd be here too
:P
the whole time i’m thinking he has a death wish lmao
I am so happy to see good chemist content on youtube!!! FINALLY!!! keep it up guys! from a fellow theoretical organic chemist
It’s scary to work with As
....says the guy who has videos of him sticking his hands into different solvents.*
Also, yeah, mixing arsenic and oregano is going to get crazy. ;-)
*Granted, I'm assuming you knew your sh!t and weren't putting yourself in any danger......it's still hilarious.
How much toxic chemicals you want to use sir?
This guy: yes
Do more organoarsenic chemistry! So we don't have to do it :)
Very green chemistry... glowing, phosphorescent, radioactive green chemistry.
Exactly the kind I like the most.
A recipe for disaster yet interesting chemistry. Arsenic, chlorins, benzen, all the good stuff is there! well done! :D
I once had to distill self-made antimonypentachloride which also cost me nerves.
I want to see the cleanup from this. Holy hell
A nightmare, just in time for halloween
Triphenylarsine is a ligand with similarities to triphenylphosphine. I'd like to see some complexes of them.
I am currently doing my PhD with an focus on arsenic based ligands and regularly synthesize AsCl3 and volatile organoarsenic compounds in 50-200g scale. I advise the utmost care with the contaminated glassware and during the preparation. A lot of these compounds easily break through gas mask filters. It excites me to see somebody else doing similar chemistry - I’m usually getting weird looks from colleagues - but make sure you are working in a controlled environment.
Why are you synthesizing such large quantities in a research setting?
Hi. Is the danger overrated? Alchemists sometimes made Arsenic trichloride in kg quantities without all modern day precautions
What exposure effects, if any, have you experienced?
@@gregoryb9313ligand precursors. And you have to distill that stuff.
@@baiseduezcke2295none - due to proper training and equipment. But a mistake or accident can always happen
very nice. as an organic chemist, working with arsenic is treading into serious uncanny valley territory. i applaud your resolve and fastidiousness during this synthesis and look forward with the work you'll perform with this ligand! definitely some cool complexes that can be made or some tetraphenylarsonium chloride to keep around the lab. good luck, and stay safe :)
Could you explain why this is “uncanny valley” territory for a curious non-chemist?
Arsenic is notoriously poisonous. This would be bad enough on its own, but when you make organoarsenic components you combine that toxicity with the ability to penetrate skin and sometimes even protective clothing.
I'm a biochemist, so I don't go near any of this freaky stuff. But I do grow lots of gross bacteria (like 100 gram batches of pure E. coli haha), I'm sure some real chemists might not be keen on that.
@@nerd1000ify The nasty form of arsenic is As(III) inorganic compounds, organoarsenic compounds are less toxic than that, they are toxic but not as dangerous.
@dur shurrikun there are even some non-toxic organoarsenic compounds like arsenobetaine. But most of them are troubling enough that you'd prefer not to deal with them.
Cacodylic acid is a popular buffer for electron microscope samples in my field, we always treat it with much respect.
@@nerd1000ify In general, the most dangerous form of arsenic are inorganic compounds of Arsenic (III), like As2O3, arsines are less toxic than them while Arsenic (V) compounds are the least toxic.
To avoid fuckups due to suck-back, make a habit of placing a safety bottle between the water trap and the flask you want to protect. It prevents dangerously high blood pressure and head shaped dents in the wall, trust me. 😡🤕
Can you do a video on cleaning and decontamination please. Nearly no one does this.
It is one thing to know you can work with arsenic safely. But then is the "now what?" moment when you need to dispose of the 65% non-yield and clean all your glassware.
I already finished it so I can't record it, I also prefer to focus my time on a new project. Any solvent that was distilled off I disposed of normally. I evaporated off solvent containing arsenic compounds and put any solid waste into a bag. Liquid waste that is contaminated (from cleaning) I put in a container. They will eventually go to municipal chemical waste who has to take it and process it.
@@Chemiolis It was a general comment rather than a specific request for this project. There are plenty of synthesis videos, but almost nothing on responsible practice. Cleaning and disposal is never sexy, but I think it is important: whether we are talking organic tars, halogenated compounds, heavy metals or reactive anions.
That short-path condenser is cute! The star of many of your vids.
What an amazing video! I loved seeing every part of your synthesis right up to the triphenylarsine crystals at the end.
Have you ever thought about making Cadet's Fuming Liquid? This is made from potassium acetate and arsenic trioxide and consists mostly of dicacodyl and cacodyl oxide. These were the first organometallic substances prepared and I've never seen any pictures let alone videos of this substance.
It would be amazing to see someone synthesize it!
Excellent presentation.
Hyped up for any complexes you might make with it.
Very interesting. Can’t wait to see more!
Yes, more organo-arsenic chem. I appreciate your alchemy sir!
Love to see my suggestion coming to fruition ❤️
Would be cool to see some complex with this ligand! Also, as for other weird chemistries (not strictly organometallic), organoselenium compounds are kinda cool, but in my experience somewhat annoying to work with (some compounds just extrude elemental selenium kinda randomly, which is very unhelpful).
pentaaryl bismuth(V) is purple if I remember correctly, vaguely remember something ab oxidation of the triarylbismuth with chlorine followed by disproportionation. Worth a try, maybe with a different aryl group to increase stability of the compound.
" The pentaphenyl compound is deeply colored and thermochromic, possibly because of an equilibrium between square pyramidal and trigonal bipyramidal structures" mmm,, berry pseudorotation
The reaction was cool by the way. I want to see TDMAT preparation.
Inverted funnel traps are the bane of my existence. I switched to using a long straight 24/40 tube because it has a lot more wiggle room than a little funnel because it can fill with more liquid before it coming over. What is your fume hood setup? Must be rock solid if you are willing to do organoarsenic chem!
I constructed a hood with a similar area as the commericals ones and bought a 2nd hand fume hood centrifugal fan for the airflow and connected that to it. A lot cheaper than buying a commercial hood which is basically just a plastic and glass box (and the wrong size for me). I looked into the actual toxicity of the compounds (not too crazy) and wore a respirator with a B2 filter constantly. Arsenic has been worked with for a long time in human history, yes it is quite persistent and nasty, though it can be worked with safely if we consider today's standards and protection. I won't work on different arsenic projects back to back just to be sure that there is no chronic exposure.
@@Chemiolis makes sense! Doing something similar is on my list as well.
How did you decontaminate the area? AsCl3 turning into non-volatile chemicals on surfaces is spooky.
Super impressed by your videos! Your channel is going to seriously take off before we know it :)
@@nomcopterlabs Thank you! My whole fumehood is covered in black paper and black vinyl (as backgrounds) so I can simply remove these to clean it. I can't really do anything to the ducting but I don't think there is really that much of an issue anyway, since the quantities are so small that it won't really matter even if you lick it ;)
Your channel is what NileRed could have been in a more fortunate universe
So true!
It's what NurdRage 2.0 (who, incidentally did his PhD in organometallics). This channel definitely filled the lack-of-NurdRage-content.
Do you have access to an instrument to profile your final product's purity? I'm guessing youd need an NMR machine though since I don't see any of the cheaper options like gc/hplc/ms/fid that make o-chem characterisation cheap and easy 😥. Also lol for someone who seems to be fairly adept, cmon you didn't see that suck back coming? Haha😆
@@wither8 most of time NMR is for qualitative analysis, more to say what is this byproduct, not how much and how pure stuff is. For purity indeed you use GC and HPLC (quantitative).
wym more fortunate universe? what happened to NileRed?
@@arturc.6504 Capitalism, algorithm and money do not promote complicated videos, that is why he mostly make shorts now
Amazing stuff
It is so nice
Getting a used rotovap online would make your life so so much easier
Hello. I have a weird idea for some time now.
I wonder if we can isolate the cobalt metal (Co) from cobalamin/cyanocobalamin (Vitamine B12) by some method (maybe burn the cobalamin or anything).
I'm not a chemist and this just showed up in my feed. The 'click' label implies that the components just snap together and hey presto, eureka etc., which is belied by this convoluted and seemingly dangerous process given some of the comments to date. I don't think that complexity and or novelty are necessarily deserving of a Nobel prize. What is the cost benefit of the process given the issues raised by the commentators, such as laboratory safety, practioner health and environmental safety? What benefits accrue to humankind if any, or is this another man made chemical disaster for future generations to manage?
The sodium was looking like someone took a bite out of it.... did you snack something?
I couldn’t resist
Have you noted the similarities between triphenylarsine and desoxypipradrol? I wonder how toxic triphenylarsine or an aminated homologue would be at milligram doses
Interesting, I'd be curious to see how organoarsenics measure up to other pnictogens in terms of properties. I'd also love to see some high valent organoiodine compounds: orgsyn gives a prep of diphenyliodonium iodide from iodobenzene.
Dess-Martin periodinane when? I(V). There's also diacetoxyiodate(I) and diazidoiodate(I), but the latter involves potentially dangerous trimethylsilyl azide.
@@californium-2526 That last one sounds terrifying...
@@Zenzicubic Diazidoiodate(I) is truly the most hypervalent iodine compound of all time. That and diacetoxyiodate(I) tend to have polymer-bound quarternary ammonium cations as their countercations.
Arsanes are like phosphanes, they are just very good nucleophiles and ligands, there's not much else about them.
They can get oxydised to arsine oxydes and that's really it, there's also arsonic and arsinic acid.
They are also very weak bases, they are very unlike amines.
And the heterocycles of arsenic, mainly Arsole and Arsinine are only of academic interest and they have very little aromaticity, they aren't as interesting as pirroles or pyridines.
For my phd, I could make ruthenium coordination compounds with triphenylarsine as ligands and study what havoc it could wreak on the mitochondria of tumour cells.
So, did it help against tumours :)?
@@Chemiolis I haven't started applying for Phd yet.
Still a Master's student.
how did you handle cleanup and waste disposal?
I would agree that not using powdered sodium probably was the reason for a lower yield. I recently repeated a reaction that another researcher in our lab had done before and I got a much better yield because I used a powdered reagent rather than a crystalline reagent.
How does one even get powdered sodium? Isn't it really soft, kind of like clay, not really the sort of material that can be turned into a powder? (And of course, it would be harder to handle, due to the increased air- and water-sensitivity.)
@@alexpotts6520 I think you can powderize it by precipitating sodium metal by doing a reduction reaction with a sodium salt. I know people do it with potassium to make "potassium sand," and you can even purchase powdered potassium from American Elements.
@@user-ko7lz3kr1d Well you need a pretty powerful reducing agent for that! And moreover, the reaction would somehow have to be done in the solid state to get a powder, otherwise you'd just end up with molten blobs of sodium coalescing into a ball, so it's not just a school-level smelting-type reaction.
Would like to see some organoselenium chemistry if you have the materials for it, did a lot of it for my masters thesis if you want any ideas :)
Thumbs up! Do you know, if Benzene could be replaced by Toluene (which is much easier to obtain, since you don't want to run a dry distillation of a mixture of Na-benzoate and NaOH, in order to get some Benzene)?
Toluene has already replaced benzene as the solvent, almost nobody uses benzene in labs anymore, except as a reagent when it is needed.
@@durshurrikun150 I know: This was already state-of-the-art back in 1978, when I began my vocational training.
Heavy-metals in organic compounds
Benzene
Arsenic in general...
This entire synthesis sounds like a toxic cancer risk.
Great video! Looking forward to see some nitrogen chemistry :)
Powdered sodium would be awesome to see used!
8:10 forbidden brownie
8:22
Arsenic and Benzine
Sounds yummy!
organometallic Chemistry is the future of the materials, Do more it´s interesting for enjoy advanced chemist
Does the reaction with sodium proceed through an organosodium compound or does it proceeded through a radical pathway?
Which chemical used 2.4 volt torch bulb filament fails when the torch focuses on copper metal
How do you prepare powdered Sodium unless you use a metal salt?
As I understand it, the stronger bonds in organic arsenic compounds makes them less toxic - perhaps even non-toxic - as they do not react with proteins. Inorganic arsenic compounds are considerably more toxic. Nevertheless, I would be very wary working with them.
Scary stuff, though interesting
What do you need triphenylarsine for?
Is there such a thing as a quaternary arsenic compound?
I'm wondering what kind of ionic liquids you can make with organic arsenic analogs , at least with a protonated tertiary...
I'd love to see what you come up with, even if it's just a suggestion.
Look up tetraphenylarsonium chloride
They exist, they are like phosphonium and ammonium ions.
@@durshurrikun150 yeah but where do you find such things outside a lab & what are they called?
@@petevenuti7355 Some quaternary ammonium and phosphonium salts are in commerce, you can buy them, they are used as phase transfer catalysts or as non coordinating cations.
One being tetrabutyl ammonium chloride.
You won't find such a thing outside of a lab because most people outside of a lab don't need them.
Or you can make them by alkylation with the corresponding tertiary phosphine, amine and an halogenated alkane
Don't beat yourself up over 38% yield. For research-level quanttites I'd say that's perfectly acceptable. A decent job.
Next chemical abomination could be diphenylaminechlorarsine (Adamsite), what a useful ligand to make! :)
how triphenylarsine reacts compared to triphenylphosphine?
now i know what to do with all the arsenic i have in the yard ......(not kidding theres lots of arsenic sulphide where i live)
Its not the arsenic so much, or that its an organoarsenic compound, its that it structurally resembles and has a synthesis similar some, umm... very spicy arsenic compunds that were popular in Europe for a while from 1916-1918...
Why you have not tried 2 methyl isoborneol yet?
It is more easier to synthesize it than geosmin and both are same in terms of their smell.
i find 1:30 quite funny because the last time i used a pool cleaning tablet i licked it and food didn't taste the same for a month afterwards
arsenic tri cubane?
1:22 chemist doing physics be like
My zip lock trick lol I get a shout out? 😀 Some materials are really stubborn to powderize. Dried tree Roots are my least favorite...
Lipophillic arsenic compound: Nothing stated about toxicity on wiki. I'm guessing it's not good 3 or 4 on heath diamond?
Freeze in LN2 before grinding. Well that's my strategy with otherwise un-grindable stuff.
BRO MADE MALWARE IN REAL LIFE😭🤯🤯
Benzene as a solvent? Thats some old school sh*t😂
I feel kinda bad not understanding shit on what's going on here (I only watch nilered)
Dammit, now I want to see an arsa-Wittig, or an arsa-Appel, to make already quirky reactions even weirder 😁
Arsenic heterocycles are not that interesting and aren't that useful, in addition to that, the aliphatic heterocycles aren't going to be stable towards oxydation.
@@durshurrikun150 Honestly, I didn’t care about the end product at all when I made that comment, still don’t. I just like the reactions themselves ^^
@@elijahberegovsky8957 I don't even know if an arsa Witting can ever happen, Aza witting happens with imines, but the equivalent of imines with arsenic are unknown and probably can't form at all, so you can't have the arsa witting reaction.
As for the appel, is there an aza variation for the appel reaction?
@@durshurrikun150 Wittig reaction uses PPh3 as a catalyst. One can use AsPh3 or some other arsenic based compound instead, to get the same result with an excellent regioselectivity. That’s what I meant as an arsa-Wittig. Here they try out a whole bunch of compounds both as substrates and as catalysts: “Systematic Study on the Catalytic Arsa-Wittig Reaction” (no doi ‘cuz the comment kept being deleted)
As for Appel, I haven’t seen papers that use AsPh3 instead of PPh3, but I think it’s worth a try
Making lewisite with arsenic trichloride
We had like….TWENTY FIVE GRAMS of triphenylarsine in my lab just…..sitting around. Like….WHY???!!!! I disposed of that shit IMMEDIATELY
Is this guy immortal or something?
Wow I don't know anyone that makes triphenylarsine with arsenic metal.
I accidentally poisoned myself with arsenic gas/vapor last month. And im just now starting to feel normal again.
I think i almost died (AGAIN) lmao
Didnt go to the doctor because i dont have health insurance... but holy shit.
I had a terrible cardiac arrythmia for 2 weeks. Then for two more weeks whenever i got stressed or physically exerted the arrythmia would come back.
I really fucked up my mitochondria!!!
Havent had any issues for almost two weeks now.... but i still feel weird sometimes.
ARSENIC SUCKS.
(Noone ever told me that treated lumber is soaked in an arsenic compound... THIS IS A PSA
Don't burn that shit. Whatever you do lmao)
I think that you might have been poisoned with arsine, AsH3, a colorless gas with a mild garlic odor, not free arsenic, which is a solid under normal conditions.
How did you do it? What chemicals were you working with?
Idk how I ended up here. Ig i watch too much Nile Red 😂
Fun Fact: Arsenic was and is used in medicine.
Arsenous acid! 🤣
Awesome! Bet you also created a lot of biphenyl gunk through Würtz coupling lmao.
megabased
Hm, very dangerous - and so many contaminetd equipment to clean up... really no fun.
Is combining alkali metals and halogen hydrocarbons really recommendable? 😟
Condensers aren't made for heat reactions - better use a original reaction pipe for it.
Funnel traps are used to prevent suckbacks while gas washing - but it only works if the funnel isn't dipped to deep into the liquid, just a few millimeters.
This looks like PCP ngl
PCP с мышьяком. Ммммм вкуснятина...
You are mad
I wouldn't mind more arsenic chemistry ⚗️🧪. And Happy Halloween to you too! 🎃
Wonder if anyone can do something with Thallium 😮