Making β-Nitrostyrene so I can be like Shulgin

Today we honor one of the goats of chemistry, Alexander Shulgin. I also learned that I might have achieved a new level of stupidity due to me not reading the procedure correctly. Enjoy chemistry kings and queens.

Title credit: @.Steelio on Discord

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[el_kokas-pz]

I would never imagine I'd see the words "making" and "shulgin" together in a YouTube video

[saschalinz]

T. Shulgin R.I.P! Thank you for your insane work! Also Tikal!

[alexcronvich]

Watching this video with my phone propped up on PiHKAL & TiHKAL was absolutely surreal

[LabCoatz_Science]

I made some of this once from almond extract and RC fuel, lol...no crystals though, it was more of a test than anything. Great video, Shulgin would be proud of that +95% yield!

[girrrrrrr]

Whoops idk how this video got downloaded to my computer.

[MoxxoM]

Yeah, β-Nitrostyrenes just oiling out is annoying.

Beautiful crystals you got there. But the 2, 5-dimethoxy substituted ones are even prettier. Those shiny/sparkling bright orange crystals are a feast for the eyes.

Great video. Keep it up.

[gaetonzorzi]

I really appreciate you taking the time to make videos about certain questionable compounds, they’re more interesting than most other people’s chemistry videos. And way to pay respect to Shulgin 😊

[shinymonktouchymonk]

Best video and channel on yt !!! I was a
Chem major at Santa Clara University
In 1973. I was 2nd in my class. Ended
Up as a Dana Point, California Real
Estate Broker for 45 years. Now retired.
Still think Chemistry is the Language of
the Gods!!! Absolutely Fascinating !!!
Mark

[jonhoyles]

well done sir enjoyed that, we all miss alex his methods of figuring out new pathways of subtituted phenythlamines hopefully that research continues its interesting to know whats still possible discoverable new compounds with research

[Anilinequeen]

When he said “I’ll redo it” I was like yay more chem! Also if possible I’d love to see some purity analysis, NMR perhaps 🤔 I just like data

[jaimeortega]

Shulgin was a great man who had a rare talent of being able to predict certain things in the future. Still wish I had all his letters from the early 90s.

[MRblazedBEANS]

As someone who is a huge fan of shulgns work I would personally love to make a large batch of 2C-B or my favorite 2C-I. It's such a amazing drug it sucks very few humans have tried it. It puts mushrooms and lsd to shame nearly impossible to have a bad trip on 2C-I set and setting doesn't seem to matter with that class of drugs. The body feeling of mdma with the crazy visual of high dose LSD.

[stefanstark]

I know a similar synthesis with nitroethane and benzaldehyde.
N-butylamine was the base. This was perfomed without any water but toluene as a solvent.
By refluxing with a dean stark trap the water was removed. As water is one of the reaction products the reaction was driven forward and after cooling down the toluene and recrystalizing from isopropanol the yield was about 95%.
Nice bright yellow huge needle like crystals which cause allergy like Symptoms upon skin contact.

[chrisj]

Still my favorite online chemistry teacher! I remember reading thru Sasha's findings and being absolutely obsessed! Even managed to make it out to his property once! I'm so lucky to find so many interesting people in this life

[zenmark]

A convenient part of doing stuff Shulgin did is that you can absolutely do it in a shed. He already proved that :D

[nilnull]

Wording in procedure is so damn important. I wanted to prepare N-(2, 4-dinitrobenzenesulfonyl)-2-formylpyrrole by reaction of 2-formylpyrrole and dinitrobenzenesulfonyl chloride. But couldn't get it done with KOH as base (according to procedure). Had to do it with NaH and still got only ~20% yield (report with KOH gave ~55% yield).

[jaimeortega]

Great job and great yield! Good that you caught where you went wrong in the procedure - sometimes finding that is tricky.

[cclarity]

That recrystallization was some of the coolest shit I've ever seen

[zonex]

If it is hydrogenated, it will be phenethylamine (amphetamine's cousin)

[Grnter]

It is likely that beta-nitrostyrene can crystallize into a few different polymorphs, hence the differences in color/recrystallization patterns. It would be really interesting to isolate a few of the polymorphs and perform a melting point analysis on each of them!