> chemistry > divers-organiques > cubane-chemistry > cubane-synthesis > project-plan-cubane-synthesis-extractions-ire

Project plan: Cubane synthesis

Extractions&Ire - 2020-08-05

Outlining the plan to synthesis Cubane-14-dicarboxylic acid in my garage! A project of many steps, but there's some classic organic chemistry protocols in there, and I like a challenge! (and people like watching me struggle lol)
1997 Lab scale paper: https://www.researchgate.net/publication/244572672_Dimethyl_Cubane-14-dicarboxylate_A_Practical_Laboratory_Scale_Synthesis
2013 Pilot Scale: https://pubs.acs.org/doi/abs/10.1021/op400181g

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Extractions&Ire - 2020-08-05

Next video in this series should be out this weekend!

Kerem Diren - 2020-08-08

try doing cyclooctatetraene next time

kev - 2020-08-27

i know you were receiving complaints about the cussing... but fuck that, the cussing and the quirky video edits were brilliant! it made it extremely enjoyable for my learning experience.

cool band too btw!

Edward Gentle - 2020-09-18

Hey why do you need and UV lamp, you live in Australia don't you?

R Johnson - 2020-09-25

Dude!
Thank you for making all these awesome videos!
I always download your videos. But sometimes your video gets removed, and with that, the links in the description are also deleted.
Perhaps, you could add the titles/DOI etc. as a text in the video?

Bootstrap Han - 2022-01-02

How viable would the octo be as a rocket fuel?

Ok Ok - 2020-08-28

I love how panicked E&F is all of the time. It's like he's trying to teach you all of this before the feds break into his lab.

A A - 2021-06-04

@Lachy Maccas language is but a crude reflection of this shit we all experience

Nicolas Sever - 2021-07-31

It's the amphetamines

Lachy Maccas - 2021-07-31

@Nicolas Sever nah he's definitely not a bee lol

togoth1 - 2021-12-17

also... ADHD... at least that's what his speach sounds like to me. Just like my wife😂

Nick S - 2022-01-19

Lol 😆 so fucking true!

A. H. - 2020-08-05

so, could a failure during detonation testing of your product be called a cuban missile crisis ?

Diego Hernandez - 2020-09-20

And if a chemist working on cubane gets fired from their job then it's a "cubane dismissal crisis"

P. O'Neill - 2021-03-19

Or Maby the CUBANE MISSILE CRISIS? I know its a Lame Joke

Sidhant Tomar - 2021-07-05

cuban fissile crisis :D

Maple Sunrise - 2021-12-22

would a person blowing his head off doing this be called Kurt Cubane?

Guy Stokes - 2022-01-10

@Maple Sunrise 9 months later and a nirvana joke??? Fucking chemists

SIGSEGV - 2020-08-05

ah yes, Minecraft chemistry

Admiral Mudkip - 2021-07-07

Minechem is a minecraft mod that adds chemistry.

Phobos - 2021-07-21

@Admiral Mudkip yeah ?

Alex Potts - 2020-08-05

If you pull this off, it might just be the most impressive amateur chemistry project anywhere on YouTube.

Rhodanide - 2020-08-05

When I said "Just make Octanitrocubane" on your previous vid, I was only joking....
But shit, that's a BRUTAL call of the bluff!

BuickDoc - 2020-08-11

@Extractions&Ire How about dry ice in a small Dewar in your freezer? You might have to replenish the CO2 every couple of days.

Dank Hill - 2020-08-23

@Extractions&Ire Ok, make Chlorine trifluoride HA GOTCHA.

Grant Flippin - 2020-09-03

@Extractions&Ire you can't synthesize a stable yet highly explosive liquid

Sophia Astatine - 2020-12-06

@Dank Hill I've made that request for a while, but I've come to realise that fire that unquenchable hellfire is not suitable for the natural habitat of wildfires. Could light all of Australia on fire.

a smol bean - 2021-06-22

Just make octanitrocubane tho 🙄

Archie Piatt - 2020-08-05

If you actually make the octanitrocubane like everyone is shouting you will get de facto chemistry bragging rights.

TheApexSurvivor - 2020-08-06

@Extractions&Ire honestly, if you do a decent enough synth that you can repeat, the military contracts it could open up would probably be worth more than a full time job, plus a few contracts on your resume and a few reproductions and improvements of the synth under your belt would open up some pretty decent jobs if you still wanted more money.

Ries van Wijngaarden - 2020-10-03

@Extractions&Ire Don't sell yourself short mate, my granddad had a job in the field and he was just a farmer!

Israel Burkett - 2020-10-09

Extractions&Ire I feel like the shed is better than the field lol

Balls Inspector - 2021-12-19

@Extractions&Ire make the boom cube

Susynoid0458 - 2021-12-27

@Extractions&Ire what if I threw in 5 bucks?

Kevin Bauer - 2020-08-06

Tom, have you ever read "Ignition! An informal history of liquid rocket propellants", by John D. Clark (with a foreword by Issac Asimov)?
Just a very entertaining read, as well as ideas for a lot of things that I shouldn't try myself. He was involved in the research community for 20 years, yet managed to keep 10 fingers and two eyes - all attached!
I'm not on your Patreon yet, but would be willing to send you one if you don't have it. It's pretty light reading for fun, but probably leaves enough clues to research if you want to follow up with some synthesis.

Peter - 2020-08-05

You always make me thnik I matter and I can be good at chemistry even through the fact how big of a shit I’m. Your videos bring sunshine into my life. THANK YOU TOM, THANK YOU!

Extractions&Ire - 2020-08-06

Thanks for watching the videos mate, glad you enjoy them! And yes, you don't have to do good at the chemistry to be good at chemistry, the point is the trying

Zach Russ - 2020-10-13

@Extractions&Ire wholesome chem vibes

Lorenzo Lafayette Quadri - 2020-08-05

Make sure you use the right type of glass/quartz when using deep UV.

Jacob Ellinger - 2020-08-05

can't wait to see what yellow mixture you end up with ...

Celiane - 2020-08-05

To defeat the enemy, you must first know the enemy. Or get intimate with the enemy. All up in it's gross yellow-ness.

TheApexSurvivor - 2020-08-06

Nah, it'll be green and trying to turn it blue will result in it tarring up...

Tim Williams - 2020-08-06

That Diels-Alder step could go lots of ways I'll bet

lordchickenhawk - 2020-08-16

Scrolled down looking for the inevitable yellow referencing comment...

Justin Hughes - 2020-09-24

Ded

CVLPER - 2020-08-26

One of the most under-appreciated chemistry channels on YouTube.

James Edwards - 2020-08-05

E&I: Here's the extremely in-depth explanation of the synthesis
Me: But will it go boom?

Andrew Esther - 2020-08-06

Probably just “pop” on some tin foil. But let’s be real, that’s why we’re all here.

GerSHAK - 2020-08-06

@Andrew Esther :D

Justin Hughes - 2020-09-24

...grace my cerebellum.

Roth - 2020-08-07

ive been watching for a while and uhh, im starting to realize how he seems to be more and more slipping into the "Mad Scientist" Archetype. I couldnt be more excited!

markiangooley - 2020-11-03

Back in college I wanted to make dodecahedrane but realized I’d never get far. Then I discovered that a group (or was it mostly a solo effort?) had made a lot of difficult progress, and they finished the synthesis a few months later...I think the result was published in 1982.

Finghin McCarthy - 2020-08-25

is it just me or have others learned more chemistry from this dude than their lecturers

movieboy6 - 2020-09-08

I switched my major from chemistry to mathematics, but I always love these videos that bring me back to all the stuff I learned in the Orgos. Cheers!

Jacob Van Buren - 2020-08-06

“Ligma-Aldrich” now this is the quality content I subscribe for

Jacob Van Buren - 2020-08-09

P McR https://knowyourmeme.com/memes/ligma

Edgar León - 2020-08-19

@Jacob Van Buren Man, you are such a pure and saint soul for not answering with THE answer

Stitch Finger - 2021-09-28

@P McR Sigma-Aldrich is a chemical supplier

Nan0Scho1ar - 2021-10-26

Ligma baldrich

Vulpeus System - 2021-10-27

@P McR LIGMABALLS

Marc G - 2020-08-05

Is it finally time for the promised octanitrocubane synthesis? <3

edi - 2020-08-18

@Alexander Van Graff LOL

Edgar León - 2020-08-19

@Alexander Van Graff Time to pull off a transmutation in my backyard.

Alexander Van Graff - 2020-08-19

@Edgar León David Hahn did nothing wrong, history will vindicate him

Edgar León - 2020-08-19

@Alexander Van Graff F

Edgar León - 2020-08-19

@Alexander Van Graff I didn't know anything about Hahn's case until now

07actual - 2020-08-06

I'm beyond excited to see how this project goes. Even if it all becomes yellow/tar.

Venonim - 2020-08-05

Oh yes. Finally!!! I’ve been waiting for this synthesis for soooooo long. I’m very glad you’re going to do something around this cubane topic.

BlockOfWood - 2020-08-06

You've really been improving recently, it makes me almost think you'll be able to finish this project.

Boomproof - 2020-09-20

You're a great chemist! Thanks for sharing your knowledge with us :)

Облако - 2020-08-05

Another great mind descending into geometry-obsessive madness... This is how science will meet it's end on earth.

Extractions&Ire - 2020-08-05

Too many goddamn CURVES on this earth

Andrew Esther - 2020-08-06

Extractions&Ire #cubeearththeory

a2pabmb2 - 2020-08-06

@Liam Cube... into HORROR!

Mike Blah - 2020-08-06

If you guys haven't you should watch a playthrough of this shitty game called cubeworld where the comments become the plot almost literally. Someone I knew from hs speedran it

Rob Newland - 2020-08-05

Interested in how you're going to perform the photo-[2+2] reaction.

Crab Crab - 2020-08-05

Well, the second synthesis seems quite feasible. (Especially compared to the original one.) Good luck with the project!

memberwhen - 2020-08-05

it's way more fun to start new projects than finish boring ones. TRUE STORY

David Vycheslavovich - 2020-09-09

Very ambitious project for an amateur chemist- mad respect!

David Hill - 2020-09-27

Do it! You can do it! I've always loved the queue been structure but usually I see it was not a group taking off, and like a chain of the basic cube joining up and Nitro groups on the other four corners. Apparently extremely explosive when it set off! Had a friend served 12 months at her Majesty's Royal Apartments after accidentally stumbling through a military base, and amongst other things, ending up with a few grams worth which caused quite a stir involving everything from police to tactical response, the antiterrorism unit, the army and the SAS or getting involved to track down where the stuff had gone, and then find it… Helicopters and all!!! Not the brightest, he asked a chemist friend how it's detonated and what he was getting use it on, which is where they got his name and after apprehending him he thought it was funny and made it hard for them to find… And quite violent to put himself as what he was going to use and the amount would not have just levelled the building but possibly the suburb, not comprehending just how explosive tetra Nitro is. When they explained how much damage the smallest amount could do, and he thought about how much she was going to use… He realised it wasn't quite funny and with terrorism act was about to be imposed which would involve many more years. If he didn't kill himself in the process! As the amount he had although seeming small, and him thinking a chewing gum ball size would be enough to blow out a support rather than a whole building being high-quality demolition explosives, he never would have got far enough away from the building in time and I daresay take out a ferry large area sending concrete bricks and all sorts up to kilometres away. This doesn't seem anywhere near as powerful but I want to see the origami of the organic synthesis. Making rings is one thing, in chemistry we made sulphonamides bug drugs with a four member ring consisting of carbon sulphur nitrogen which was its biggest downfall being hydrophilic and therefore pretty hard to use as an antibiotic considering you gotta get past saliva, stomach acid into the bloodstream and to the bug without technically getting wet, our mission being a quantitative structural analysis of different sulphonamides and potential methods of protecting the reading either via structure, using the electronegativity of the molecule to enhance the bond, adding a cofactor or prodrug to assist getting it to work needed to be and then disappearing… Lots of fun. The QSAR involved over 32 varieties in the biology department to be funny gave us sulphonamide resistant bacteria. I decided to adjust the electronegativity of the ring by adding Nitro group in the power position, patented 1952 self-made synthesis a lot easier having somebody else already created for you, and knowing that at some biological effect already, dropping LSD before a product and re-crystallising incredibly slowly… Hoping no one would notice SO what's the crystals grow slowly, got quizzed by three PhD lecturers who just said throw it on ice, and I decided rather shakily to tell them I'm growing the crystals slowly so I get a more pure product and ended up with 99.994% pure as I'd also read that into your products block the activity. The night before a whole semester and group work was supposed to be handed in, somehow I left my bag at the pub watching three live bands and travelling through three different suburbs across Sydney, with everything and having nothing their hand in the day before the exam, got lucky in the bag turned up three days later and because my group was hopeless hard not only done it with the group but done one solo using the groups information and the lecturer said good now can find out who really did the work. Surprisingly, my drug was the only one to actually kill a resistant strain and I was the only member of the group to pass! I love chemistry! Except when the person beside me told me that albino make tri chloro tolueneTCT which is more unstable than its brother TNT and had to dob him in… Gotta love ADHD!

Aadil - 2020-08-28

When you brominated the diether, how did you figure out where exactly the bromine would be substituted, because there seems to be other viable positions for the bromination?

Lukas Wursthorn - 2020-08-05

Consider testing the photochemical 2+2 Cycloaddition with some cyclopentadiene dimer (if that reaction even is a thing, just crossed my mind). It might help establishing reaction conditions before wasting precious starting material

Adam Rolt - 2020-09-06

Tend not to advise this. I think the best method is to get reliable methods for high yields in the preceding steps and simply scale up the 'real thing' and get a good analytical method for monitoring the reaction. My experience is that you'll end up down a rabbit hole of trying to fix problems on a test substrate which may not even be an issue on the proper substrate, ultimately wasting time and making one sad.

Michael Ryan - 2020-09-13

You can't actually do this. Cp dimer does exist, but it will not react under UV light. The carbonyl group (C=O, the one next to the carbon-carbon double bond) on the intermediate in the video is necessary for the [2+2] reaction to occur.

movax20h - 2020-08-10

Yeah. I like the idea. The pilot scale method, can probably be down scalled, to follow the same synthesis path, just use smaller amounts.

Jhonny Castle jr. - 2020-09-09

I wish my family would laugh when i silently say, " ah '61. Good year.... Was it?" Still gets me everytime

Full Modern Alchemist - 2020-08-05

I cracked up at the Simpsons clip. Definitely relatable. I start way more projects than I finish too. I read a tweet from Watsky about this recently and I thought it was a good way to look at it; if you have lots of projects you can procrastinate on project A while working on project B and always stay productive in the grand scheme of things. Good luck with the synthesis! I was wondering what the cyclopentanone was going to be used for.

Kevin Bauer - 2020-08-06

Full Modern Alchemist I've determined that my true hobby is Starting New Projects!

Full Modern Alchemist - 2020-08-06

Kevin Bauer lol I like that

Eric - 2020-08-06

I was kinda baffled in the previous videos when you said "I cant make octanitrocubane it's too hard" on the main channel, im glad you made this one.
Would you consider doing a video on ammonium nitrate? Cause of the explosion in Beirut and your main channel doing Explosions And Fire, I thought it might be fitting and/or a good discussion on storage of massively dangerous substances.

Dane - 2020-08-29

I'm struggling to have a question answered, perhaps ya'll might help. Would performing chemical reactions under 2 atmosphere increase the rate of reaction while also maintaining stability or would the reaction become more volatile? Please help, I am unable to test this.

Will Murrell - 2020-09-07

Your final product looks like it could be an interesting ligand for MOF synthesis.

Triss Healy - 2021-02-09

"If you you've been watching the channel for a while you know i like starting projects"
This is a highly relatable experience

stibio syrinx - 2020-08-25

the final step (Quasi-Favorski-Rearrangement) is quite interesting! :)
Good luck and greetings from Germany...

Bob Fels - 2020-08-05

For me, chemistry is like magic (I see whats happening but I dont know why), now you explained the whole trick, but I still will be amazed :P. Thx so much for all the vids. Because of your enthousiasm and the stuff you show Im really interested in chemistry now! Cant wait for the next vid :D

sam Miller - 2020-08-05

Am I the only one who knows nothing about chemistry but loves these videos

Nathan Klaft - 2020-08-05

In the last week NileRed and NurdRage has posted.
Its been a good week.
Glad to see you guys all posting,
Your narration and sense of humor is awesome.
Like when you threw that ball into an open reaction vessel. your reaction was so real. I'm glad you include fuckups it make me feel like less shit of a chemist.
Would the cubane make any interesting salts? like Ammonium Cubate or something?

Aiex 314 - 2020-08-06

Could you theoretically add ethylene groups to the cubane and polymerize it using benzoyl peroxide? Polycubanoethylene or something like that.

Blub - 2020-08-07

I'm no chemist at all, but your videos are still very interesting.

Daniel Bickford - 2020-08-06

Since the carbon bonds at three points to make the corners of cubane, and nitrogen has three bonding points could you make a cube using nitrogen? If so how unstable would it be?

An Average Arsonist - 2021-08-25

"Its really, strangely approachable"
"Amazingly it's quite approachable"

This sounds quite familiar to a sinister color we are all too familiar with.

AKGaming - 2020-08-06

You should try to synthesise oxidane, I've heard it's some high quality stuff.

Pirated Vegas Crashes Alot - 2020-08-26

Im not a chemist, I only vaguely understand your videos. Youre still my favorite youtuber 💓

Some Guy - 2020-09-10

Seeing a man use sidewalk chalk to explain the chemical synthesis of an explosive in a shed is what this channel is all about.

Darian Ballard - 2020-08-05

I hope you do more on this.