LabCoatz - 2024-02-14
Allyl alcohol and allyl bromide are two important precursors that are somewhat under-represented in the hobby chemistry community. And since I need the latter chemical to synthesize an ultra-potent caffeine analog in an upcoming video, I'll be showing how to make both in this video! UPDATE: I don't know how I screwed this up, but the final yield was actually more like 88% based on the amount of allyl cyclohexylpropionate used. 100mL of this ester is 0.483 moles, so a 100% yield of allyl bromide would've been 0.483 moles, or 58.4 grams (I got just over 50g). Sorry for the mix up, I must've been looking at the yield based on hydrobromic acid, which wasn't the limiting reagent! Want to support LabCoatz? Of course you do! Feel free to join my Patreon here, or simply donate using the PayPal link: https://www.patreon.com/LabCoatz https://www.paypal.com/paypalme/labcoatz @THYZOID hydrobromic acid synth: https://www.youtube.com/watch?v=p6rbGGQX_qA Allyl alcohol from glycerin/formic acid: https://www.youtube.com/watch?v=Npa9Twp3dlo WARNING: allyl alcohol is toxic and highly irritating to the eyes and respiratory track, and allyl bromide is carcinogenic. Caution must be taken when handling these chemicals and their precursors (sulfuric acid, hydrobromic acid, and sodium hydroxide are all highly corrosive). LabCoatz is not responsible for harm or injury resulting from replication of the video content. 0:00 Intro 0:44 Ways to get allyl alcohol 1:29 Ingredients 2:03 Allyl alcohol prep and redistillation 4:46 Allyl bromide synthesis 6:30 Workup and yield 7:37 How does it smell? 8:09 Burning allyl bromide 8:36 What's it for? 9:10 Patron thanks and outro
Caffeine analogue 10 times stronger that you can taste.. that's right up my dark and scary alley!
Absolutely beautiful video production bro
Much appreciated man!
Nice prep mate! Also thx for the shoutout in the video description.
Absolutely man, glad you liked the video!
In university my organic chemistry professor shared this horror story in his research lab. He recieved a call at midnight that there was an incident at the research lab with one of his grad students and he needed to come right away. So he crawls out of bed and speeds over, gets to the lab and sees his grad student crying near the fume hood. He goes over and also bursts into tears, apparently the student had knocked over like 10g of lachrymators. He told us that they were unable to move since not being able to see in a lab is dangerous they sat there for 3 hours until the fume hood removed enough vapors for it no longer to burn if they opened their eyes... Not sure what they were working with because they were still working on their research at the time and you know researcher secrecy but man what an unfortunate way to spend your night. long day at work you go home just to get called in a deep sleep to go get tear gassed lol what a story.
I always pay attention to the position of everything in the lab. I had had a splash of rather dilute, about 40%, sulfuric acid in my face and washed it in several seconds after asking my friend to open the tap. If I were the aforementioned grad student, I'd just crawl out of the room. The floors in labs are seldom occupied, and, thus, safe for a human being
When dealing with these dangerous chemical, must wear gas mask (e.g. which covers eye, nose and mouth).
I have seen quite a lot of chemicals camouflage as regular products/or add a slight amount of additives just to avoid being regulated.
I don't think an ester such as this would be regulated harshly anyways, given that it is legit pineapple fragrance and has legit food uses.
Nice one bro! I’m amped for the caffeine analog video.
Same here
I remember back when I first got access to a university library in the late 90s. I had started studying IT, but I found that reading through the Merck Index was much more fascinating than coding HTML by hand in Notepad. The Merck descriptions of subjective characteristics were particularly interesting to me, but were usually only as simple as "Odor: unpleasant, acrid". I'm so glad that now Chemtubers like yourself give us the opportunity to see interesting compounds like this, as well as hearing proper detailed descriptions of their subjective properties. Your descriptions of lachrymatory/offensive smelling compounds have been evocative enough that they've brought a tear to my eye!
For language impaired viewers like me: lachrymatory means "causing tears".
Ah. It makes sense if you see it in writing instead of hearing it spoken. It comes from the Latin word "lacrima" (1st d. fem).
I think we figured out what landed bro in the hospital
Allyl alcohol is a sensitive alcohol with a double bond and concentrated sulfuric acid will destroy everything. I am also working with allyl bromide at the moment, the synthesis was achieved by careful addition of HBr 48 % to ice-cooled allyl alcohol and then the normal work-up, except that the separation was done with ice-cold conc. HCl, the yield was 70 %.
I actually redid the calculations and found my yield was more like 88% based on the starting allyl cyclohexylpropionate (100% yield would've been about 42mL, and I got 37mL). I was a bit worried about the alkene bond being attacked (mostly by the HBr to form 1,2-dibromopropane), but everything distilled over at the correct boiling point, so thankfully the process seems fairly clean despite the tar!
The allyester as a starting material is very interesting, let's see if it's available here too. Otherwise very nice synthesis@@LabCoatz_Science
If youre going to allyl bromide you dont need to break the azeotrope since allyl bromide doesnt form an azeotrope. Ive done this hydrolyzing allyl chloride to allyl alcohol then brominating
How was your yield from allyl alcohol to allyl bromide? I wonder what could be done to increase the yield to 90%+
He's gearing up to make Dimenthyltryptamine. Maybe some 5-methoxy-N,N-dimethyltryptamine. I sense it.
I've watched a number of your videos and I'm impressed by you skill level. I have a request. Methylene chloride ( aka dichloromethane) was used in commercial paint remover. The stuff actually worked and was not very expensive. A few years ago the feds banned retail sale of paint remover containing dichloromethane. This made things difficult for me but not impossible. Straight dichloromethane was still available for retail purchase and I would mix it into a paste to use as paint remover. Well, now the feds have banned retail sale of all dichloromethane. Is there any practical DIY way to synthesize dichloromethane?
In theory, yes, but I've never succeeded in doing so. I once tried reducing chloroform with Zn/HCl, which was reported to work, but nothing distilled over except the chloroform. Of course, this was one of the first experiments I tried way back in 2020, so I might be more successful trying it now. Chloroform is really easy to produce from acetone and bleach, so reducing it with the right chemical would probably be the easiest route. You could also react methane with chlorine directly in the presence of UV light, but you'd get a whole bunch of side products.
There’s a welding cleaner called Sprayon wet weld spatter protectant that’s just DCM and soy lecithin. I get it for about $2.50 a can in the US,
@@LabCoatz_Science Thanks for the reply.
@@chemistryofquestionablequa6252 I went to the website and checked the data sheet. Dichloromethane has been removed from the product.
@@chemistryofquestionablequa6252just make sure you get product #WL542 because they’re trying to pass off the tetrachloroethylene (non-flammable brake cleaner) as the DCM containing product.
Stock up on the tetrachloroethylene as well because that one is on EPA death row as well.
The idea of ingesting homemade chemicals terrifies me, lol.
As it should. It's a bad idea regardless of who's doing it. I only make exceptions for things I know are pure and are in sub-gram quantities, and even that can be questionable.
allyl goes a long way ...
My guess is propargyltheophylline by allylation then dihalogenation and double elimination. That or maybe allyl bromide + I2, then double elim to make propargyl bromide, then alkylation.
Actually, I think propargyl bromide route would work fine because there's no hydrogen to remove for bromide elimination... Nucleophilic attack by the base is still possible, SN2 or SN2' style, but whatever that makes would probably distill much higher.
Actually, the compound I made was 1-allyltheobromine (3,7-dimethyl-1-allylxanthine)...similar, but allyl instead of propargyl, and substituted at the 1-position instead of 7. I wanted to do the propargyl version (DMPX), but I couldn't get my hands on propargyl bromide. I probably could've done what you were talking about to get the alkyne group, but I hadn't actually thought of that at the time!
@@LabCoatz_Science crap, I meant theobromine! No wonder my Google searches were so bad. I miss having access to structure search.
Hmm are you by chance going for the dopamine synthesis?? 🤔
Whatever you're doing its going to be awesome man!
It'll be a while, but yes, I'm still hoping to make dopamine. I couldn't do it before the college semester started, so maybe this summer...the synth works, but it has some issues I still need to work out, particularly the Henry reaction: there are a lot of side products, and no dihydroxy-b-nitrostyrenes ever crystallizes out, no matter how much water you add. I'll probably have to use the raw reaction mix without isolating the nitrostyrene, and then use chromatography to separate the dopamine HCl from the tar.
@LabCoatz_Science with a solution that hasn't had the water added yet dip a spatula into the solution and leave it out for the solvent to dry you should get seed crystals. Well thats how i did it at least. Nitrostyrenes are probably the most difficult thing I've ever crystallized so when you get a little save it for such an occasion. Oh man good luck with school!!! I just went back for the first time in 16 years so I totally see why everyone gets so busy when it starts 🤣🤣
@user-yb5cn3np5q the short answer is I was unmotivated and lost alot of time. Everything is fine now though I finally grew up and have a decent life and can go to school again.
I remember making it from glycerol. I'm not sure what other reactants I used. Maybe oxalic or formic acid reflux? I think it was about 40 years ago...
Either oxalic or formic. The latter is thought to be a better choice
My grandpa made alcohol like a pro for years and did not knew any chemistry
If you think about it, azeotropic allyl alcohol w/ water is just forbidden moonshine.
Odd question, but why doesn't the HBr add Br to the double bond?
In my own opinion, the oxygen of the alcohol could be protonated by adding hbr to allyl alcohol and mixing for a while. Thus, slowly adding H2SO4 would only cause the water to be withdrawn. but great works.
how long was the synthesis? & how long was the distillation of Allyl Alcohol & Allyl Bromide
What the concentration of the sulfuric acid, please?
What conc. is the HBr?
Can you make another video about tesla coil, in which you show how to build QCWDRSSTC or SSTC using driver ic TC4420/4429 or fake UCC ic without enable pin. There are some suggestions like using NAND logic gates (e.g. 74HC00). The reason I make this suggestion is because in some areas where there are no reliable sellers, UCC ic is not really popular, there will be students who want to build circuits (I am one of them ) with a low budget, the problem is not the price of the IC but the shipping fee (for me it is extremely expensive). Please read and respond.
What solvent could be used for this reaction to distill off anhydrous allyl alcohol? So ethylene glycol won’t work because it can’t dissolve NaOH?
Like I mentioned, you might be able to simply distill solid sodium hydroxide and the allyl ester, but idk. It's also possible to distilled the azeotropic allyl alcohol with ethylene glycol to get an anhydrous product, which is what the paper did.
@@LabCoatz_ScienceAhh cool, could you give me the DOI number? Thanks.
Love your series! If you ever get the budget, a few things I'd love to see added because my brain can't fill them in: some amount of chemical reaction animations (I haven't done chemistry in a decade) and a list of things that the chemical can be used for at the end. Basically, molecular level "how" and an extended "why" ending. What you're doing already is awesome enough on it's own though!
like good job
Hello labcautz i just got a new lab
"So why break tradition?" uhhh HAHAHAHAH that was so casually said
Permission to Call it owl alcohol?
I'm prescribed suboxone for pain as I could no longer afford Kratom & the Kratom wasn't working anymore. If I could cycle between pain meds it would really help at keeping them effective for killing pain. The suboxone makes me too drowsy. I was hoping there was some simple chemical way to change it into a more effective, non drowsy pain medication. Like hydrocodone peps me up & kills pain until I get a tolerance. The Kratom extract is more effective at killing my pain so I can a few hours of work done. But very expensive, so is hydrocodone but my insurance pays for suboxone..Sadly it doesn't work as goo & suboxone actually causes more withdrawal than Kratom & just as much as hydrocodone. I'm hoping I can find an easy to convert suboxone into a non drowsy causing pain med.
Unfortunately there really isn’t a simple way to do that and it would most likely be illegal. Maybe ask your doctor for a lower dose of the sub oxone.
@@chemistryofquestionablequa6252 Bummer...I had no plans to try and sell it. Lower doses unfortunately don't kill pain. I was also thinking if I could remove the Naloxone from the Bupenorphine so it's Bupenorphine only. It might help, which wouldn't be illegal. It'd be like you're prescribed 2 medications & not taking 1 because it's more beneficial to not take it.
The ester is available here and I will try to saponify it with anhydrous methanolic potassium hydroxide.
Not sure how well methanol will work as a solvent here, since allyl alcohol boils at 88C while methanol boils below 70C. So the methanol will boil off first, possibly taking some of the allyl alcohol with it, and still leave a hard salt cake behind. If you want an anhydrous product, I recommend a higher boiling solvent.
I don't know if methanol or other alcohols form an azeotrope with allyl alcohol. I will do some more research. Thank you I will support your channel from now on.@@LabCoatz_Science
I have a Allyl alcohol from time to time 😬
I don't, but my bromide
Acrolein.
I’m allergic to pineapple
Wow amazing video how are you doing
Drinking chemicals ♪♪♪♪
effing narly vid
IM blocking all US VIDS every american noise i block
@@queenscorgie2200 why do I care?
Allyl bromide could be prepared much cheaper and easier: E2 elimination - adding ,2-dibromopropane to hot (e.g. near boiling) concentrated NaOH, drop by drop.
@LabCoatz_Science - 2024-02-19
I don't know how I screwed this up, but the final yield was actually more like 88% based on the allyl cyclohexylpropionate used. 100mL of this ester is 0.483 moles, so a 100% yield of allyl bromide would've been 0.483 moles, or 58.4 grams (I got just over 50g). Sorry for the mix up, I must've been looking at the yield based on hydrobromic acid, which wasn't the limiting reagent!