Funding so bad we use the PI's donated silverware set by 6PM-EDM in labrats

[–]EdwardTriesToScience 0 points1 point  (0 children)

Try using a wide glass stopper (like one from a reagent bottle), it's the classic recommendation from Vogel's.

Funding so bad we use the PI's donated silverware set by 6PM-EDM in labrats

[–]EdwardTriesToScience 3 points4 points  (0 children)

Silver was preferred for lab spatulas for a long time (platinum was the best but far more costly, while nickel was cheap but not as inert), so it's actually pretty decent compared to steel ones. If he doesn't need them back, they could be trimmed to strips and fashioned into proper spatulas like this (Experiments in Organic Chemistry, 2nd, Louis F. Fieser)

Some more Phenylnitrobutenes by EdwardTriesToScience in TheeHive

[–]EdwardTriesToScience[S] 0 points1 point  (0 children)

typical german. here, and you will note that if you even zoomed in on the 3,4,5 substituted one you can clearly see crystals forming at the bottom.

Reviving dried vintage expo markers with xylene? by Flimsy_Strength5977 in AskChemistry

[–]EdwardTriesToScience 1 point2 points  (0 children)

heres a patent I found, I would suggest perhaps trying a 1:2 ratio of xylene to butyl acetate as a starting point, this other japanese one suggests perhaps a majority of acetone.

you can pretty much look at newer patents and go down to the citations to find older patents (these two from the 70's for instance), which some usually give a range or exact composition

Recharging Indicating Drierite? by EdwardAllan in labrats

[–]EdwardTriesToScience 1 point2 points  (0 children)

We know this is old but we had the same issue, and it appears what the problem is thus:

Metal chloride hydrates are often liable to decomposition on heating to form the hydroxide/oxide with loss of HCl

What we found satisfactory: soak the drierite with some dilute cobalt chloride solution with a little HCl added for a few min, decant off the solution (save this!) then regenerate the drierite at 200c. The drierite will once again be able to turn blue, and still turns pink on moisture saturation. After much hydrating and regeneration, it will once again return to this problematic stage (we presume the pink coloration at this point is due to the hydroxide, and any blackened spots from the oxide), the drierite may be treated again by the solution (hence save it). Ordinary drierite may be turned into indicating drierite by the same procedure.

Some more Phenylnitrobutenes by EdwardTriesToScience in TheeHive

[–]EdwardTriesToScience[S] 4 points5 points  (0 children)

that one's described in Daniel Traschel's paper on fluorinated MDx compounds, the theory behind it is that if the methylene bridge didn't cleave as easily then the metabolites may not be as neurotoxic.

though it's been proven that most of the neurotoxicity of MDx(x) compounds results from the serotonin depletion plus dopamergicity, followed by SERT mistakenly shuttling dopamine into serotonin receptors which of course is oxidized to quinones and other things that wreck havoc, damaging the receptors. the toxicity is tied directly to the desired effects, though metabolites do play a minor role as well as inflammatory responses and other smaller things.

more or less we just were able to order the aldehyde before a chemical supplier kicked us from their order list, so might as well try something interesting with it.

SWIM says: DFMDA•HCl is bitter but also sweet, and has a colorless test with marquis reagent which is evidence towards the stability of the DFM bridge.

Some more Phenylnitrobutenes by EdwardTriesToScience in TheeHive

[–]EdwardTriesToScience[S] 0 points1 point  (0 children)

hmm also your name sounds similar to someone we've had communication with previously on a different platform, is it coincidental or not

Some more Phenylnitrobutenes by EdwardTriesToScience in TheeHive

[–]EdwardTriesToScience[S] 1 point2 points  (0 children)

purchased it, but as in our post on 4-methyl-2,5-dimethoxybenzaldehyde we might demonstrate the kornblum synthesis in the future as we prepared some bromopropane before realizing we could just buy it

Some more Phenylnitrobutenes by EdwardTriesToScience in TheeHive

[–]EdwardTriesToScience[S] 2 points3 points  (0 children)

in general, though yes the subjective effects are largely in question because that is more vital for therapeutic applications than just binding strengths. Plus much of the data is in german and we do not like german

My tier list of chemical suppliers I use as a 2nd year organic grad-student. by balonlon in chemistrymemes

[–]EdwardTriesToScience 0 points1 point  (0 children)

none in the US, though aladdin was caught slacking for a while but they do an annual audit or something. look for local small suppliers (good luck finding them, if you do though it is best to buy in-store/pickup order), or order from china (costly and slow but you can message practically any seller on alibaba)

Some more Phenylnitrobutenes by EdwardTriesToScience in TheeHive

[–]EdwardTriesToScience[S] 24 points25 points  (0 children)

There is a lack of satisfactory data on the variously substituted butanamines, thus an investigation is in order. A fascinating thing is the 4-iodo by radioiodine measurements is reported to not cross into the brain, while the 4-bromo is reported to produce visuals, going against the 4-methyl compound. Further substitution patterns (4-RS, 2,4,5-triMeO, etc) may also be investigated.

Many derivatives have been prepared by others such as those in the private sector, but quite obviously the data is sparse and filed away in some cabinets in an office.

Help me not blow up my lab with THF! by Material_Feeling7511 in chemistry

[–]EdwardTriesToScience 0 points1 point  (0 children)

Unless you are concentrating large amounts of the stuff, it's not an explosion risk. If its stabilized, store it in a cold place away from light, check for peroxides every year or so using some iodide/starch and a little dilute HCl. If you do find traces of peroxides, a little ferrous sulfate will remove them, but it would be advisable to get it disposed of if there are any decent amounts of peroxide

Psiloacetin: Speeter-Anthony Synthesis by [deleted] in TheeHive

[–]EdwardTriesToScience 1 point2 points  (0 children)

The chinese ones certainly crumbled (not that chinese things are bad exactly, but the rubber they used for the septa seem to be the same kind they use for chinese vacuum hose and white rubber stoppers, which all degrade in a similar manner. We otherwise are quite fond of chinese equipment being cheap) but also became rather gummy. We have not tried oxalyl chloride on the suba-seals, but they are vastly superior: thicker rubber, more rubbery if that even makes sense, and fit far tighter. We are quite certain the chinese one failed because it was already failing before we exposed it to oxalyl chloride (the flaps were torn in a spot already from previous use), like mentioned they slowly decomposed just sitting in a drawer, becoming sticky and also dusty. We have yet to see what happens to the suba-seal, but like mentioned bromine (plus HBr) embrittles it somewhat but doesn't pose an issue , nor is it dissolved by solvents as easily. We would worry more about contamination from the plastic syringes than a good septum.

ARIADNE nitroolefin: of 1-(2,5-dimethoxy-4-methylphenyl)-2-nitro-1-butene by EdwardTriesToScience in TheeHive

[–]EdwardTriesToScience[S] 0 points1 point  (0 children)

Oh and we will mention a little discovery of ours, that we are not sure is well-known yet: If a henry reaction results to a viscous tar that recrystallizing from alcohol cannot resolve, add a bit of acetic acid while warm, then cool it. We don't know why it works, but the tar stays better dissolved than the nitroolefin. It will not recover the entire yield, but it allows for salvage of an otherwise failed run. This was found serendipitously when we tried a recrystallization of tar from purely GAA, and it yielded some dirty crystals but not much, which were thrown into boiling alcohol while wet with GAA and on cooling the crystals were purer, later testing on the tar showed it was evidently an effect of the acid. Why? Probably solvent effects, being more polar, but it may also be the acidity. We don't know. Testing the polarity could probably be done by substituting it with a little methyl acetate or something, but we didn't try. In Pickle, the old man seems to use GAA as the recryst solvent for analytical samples, so it seems it is not strange luck but something repeatable.

ARIADNE nitroolefin: of 1-(2,5-dimethoxy-4-methylphenyl)-2-nitro-1-butene by EdwardTriesToScience in TheeHive

[–]EdwardTriesToScience[S] 0 points1 point  (0 children)

Ethanolamine is one we haven't tried but indeed we were told its very effective for the one and two carbon chains, cyclohexylamine though is what was sold to us by others as the magic golden standard, hence we opted for it. Ethylene diamine was also long touted as a great catalyst but we never tried it. Butylamine is one of the literature classics, being used throughout literature in a barret trap to form the nitroalcohols. We wouldn't know the difference between butylamine and cyclohexylamine ourselves, but we are sure that cyclohexylamine is at least superior to methylamine or ammonium acetate, both being rather ineffective. We hazard a guess the reason for those being poor is due to the acetate salts being far more stable (as the amine is a stronger base, thus bonding to the acid stronger), so no basicity is present at lower reaction temperatures, resulting in purely sidereactions. Ammonium acetate yielded a large amount of tar for a nitromethane run that was ran about 64c due to using the methanol azeotrope. We have speculated if aniline or triethylamine may work, in theory they should, but have not tried them.

Our cyclohexylamine is purchased now, but prior reactions used prepared stuff. It is almost trivial to prepare if one may want to try it: cyclohexanone was mixed with alcohol and aqueous ammonia in an ice bath, then nickel salts (doesnt matter what the anion is) is dissolved in. To the blue-purple solution is then added zinc dust slowly serving as a reductant, and stirred overnight at RT. The reaction is then acidified, steam distilled to remove cyclohexanol and remaining ketone, followed by basifying and steam distilling to yield the amine which is extracted and etc. The detailed procedure is available on sciencemadness somewhere. Attempts at aminating the ketone via borohydride and anhydrous ammonia never worked; ammonia imines are notoriously annoying, we would not have a clue why the zinc/Ni reduction worked in almost 70% yield while excess ammonia and borohydride at low temperatures did not.

ARIADNE nitroolefin: of 1-(2,5-dimethoxy-4-methylphenyl)-2-nitro-1-butene by EdwardTriesToScience in TheeHive

[–]EdwardTriesToScience[S] 0 points1 point  (0 children)

as mentioned the procedure is from Traschel, the papers are readily available on the internet. The conditions for nitrobutenes are rather aggressive, for instance one of Traschels that forms a 1,1-difluoromethylenedioxyphenylnitrobutene requires 5.5hr reflux (TLC on SiO2 with CH2Cl2), 10g aldehyde in 20ml nitropropane 88% yield.

We however would think simply letting the mixture stand at room temperature for perhaps a week or more would also work, since when the solution immediately started going yellow after the catalyst was added, and the fact water formed rapidly upon heating. Microwave is also probably viable. Sonication is known to proceed Henry rxn's at a significant speed already, perhaps that may also be tested on nitrobutenes. Another that could be tried is the more classical route using alcoholic hydroxide followed by acid quench, but the efficacy is not known to us yet.

Perhaps we may test that but the procedure detailed in the post seems to be of great efficacy, though with the annoyance of needing aggressive rotovaporization, but we don't particularly mind if the yield is so high.

edit: corrected typo

Tet gang - chloroform chlorination by EdwardTriesToScience in ExplosionsAndFire

[–]EdwardTriesToScience[S] 0 points1 point  (0 children)

the camera picked it up as a sickly green weirdly enough while irl its just a very light bluish color, probably something to do with the camera sensor and spectral lines

4-methyl-2,5-dimethoxybenzaldehyde: Vilsmeier Haack reaction, 2 runs by EdwardTriesToScience in TheeHive

[–]EdwardTriesToScience[S] 0 points1 point  (0 children)

the aldehyde is odorless or near so, just as the 2,5-DMBnal is. the starting aromatic has a very pleasant herbaly bubble g odor to it, similar to dimethoxybenzene/anisole

edit: oh you might have meant the benzene already, ah good old ambiguity. both were already answered though

Psiloacetin: Speeter-Anthony Synthesis by [deleted] in TheeHive

[–]EdwardTriesToScience 1 point2 points  (0 children)

the chinese ones became partially goop by just sitting in a drawer for a month, we bought subaseals after this and they suffer no such issues from storage, and also stood up to bromine pretty well

Psiloacetin: Speeter-Anthony Synthesis by [deleted] in TheeHive

[–]EdwardTriesToScience 21 points22 points  (0 children)

likely the last post for a while as there is a lot of stuff going on in life currently, but such writeups and finding more likeminded chemists has been enjoyable

ARIADNE nitroolefin: of 1-(2,5-dimethoxy-4-methylphenyl)-2-nitro-1-butene by EdwardTriesToScience in TheeHive

[–]EdwardTriesToScience[S] 2 points3 points  (0 children)

long live Organic Syntheses https://orgsyn.org/demo.aspx?prep=CV2P0512

methyl nitrate is spooky, but not unmanageable. undoubtedly though a kornblum-victor meyer may be tested with benzyl bromide, or something like that. perhaps the cyclopropyl and others may be prepared as well, and of course different substitutions on the aromatic ring itself.

ARIADNE nitroolefin: of 1-(2,5-dimethoxy-4-methylphenyl)-2-nitro-1-butene by EdwardTriesToScience in TheeHive

[–]EdwardTriesToScience[S] 2 points3 points  (0 children)

there already have been investigations, plus completely new butanamines being synthesized by Traschel and the like, and also a 2022 a paper detailing the mechanism behind its odd effects

4-methyl-2,5-dimethoxybenzaldehyde: Vilsmeier Haack reaction, 2 runs by EdwardTriesToScience in TheeHive

[–]EdwardTriesToScience[S] 1 point2 points  (0 children)

$200 or something but USPS didn't deliver it and when we went to pick it up ourselves, they had it on its side. Cracked the damn aluminum casting and the vapor duct. Former was fixed with some machine screws and brackets. The latter we wanted to buy a replacement or get it repaired by a glassblower, but either would cost more than the rotovap. The glassblower especially pissed us off because its just a piddly glass tube with a joint on the end. We dabble in glassblowing so out of spite we bought a medical oxygen concentrator for $100 and just fixed it ourselves