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Author: Subject: Best and worst smelling chemicals?
Metacelsus
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[*] posted on 20-1-2017 at 21:07


I've worked with 1-bromo-2,4-dimethoxybenzene, and it doesn't smell that bad. It's interesting how a small difference in structure has this effect.

Of the chemicals I've used:
Favorite:
Benzaldehyde

Least favorite:
Thioanisole




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[*] posted on 20-1-2017 at 22:15


Phenylacetaldehyde smells like the purified essence of roses.

I really do not like the smell of sulfur dioxide.




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[*] posted on 22-1-2017 at 05:29


I quite like the smell of SO2 actually, as long as it isn't in sufficient concentrations to prove physically irritant and choking.

Chloroform is another favourite, dichlor slightly less so, since it lacks the sweetness, but still fairly pleasant.

I saw someone mention EtOH denatured with EtOEt earlier...what exactly is the point of that? diethyl ether, diisopropyl ether are quite potable, and can be used for some inventive cocktails. EtOEt has a more pleasant scent and taste than does diisopropyl ether though. If its just ethanol and ether, nothing like MeOH, pyridine then it should be perfectly drinkable. Although I'd prefer it without the EtOH, personally.

Other favourites would be nitrobenzene, benzaldehyde and the lower nitroparaffins, nitromethane and nitroethane smell quite lovely.


On the other hand, for some reason I have a particular hate for hypochlorite, theres just something about that sickly stench that turns my stomach.

About the worst though, was the (unidentified) result of attempting distillation of bromethiazole (the brominated homolog of the sedative-hypnotic chlormethiazole). In fact, either of the two, attempted distillation at 1atm and whilst apparently it can be done, with the base (salts are a bugger to form, at least, stable ones, best not to bother) a sep funnel used to attempt purification was, after washing, foul enough to require the gas mask before entering the lab. Left the window open for several days before that awful stink cleared out. There was some product certainly, in the post-rxn fluid (metabisulfite cleavage of thiamine, to thiazole-2-ethanol followed by SOCl2 or equivalent, if anyone fancies trying it. The stench of overheated product was terrible though) the entire lot went down the drain, something metallic, mixed with sulfurous overtones. Not exactly rotten egg H2S, quite hard to describe.

The haloethyl thiazole compounds themselves though have a really pleasant, quite distinctive smell to them, chlormethiazole for example, is like...fermenting apples, somewhat ethereal, with metallic overtones. Smells an awful lot better than it tastes though. At least going down. Not so bad coming back up post belching after ingestion of the drug in capsule form (not sure average gelcaps would survive it though, I take it for seizure prophylaxis/stopping one as it begins and it comes in REALLY thick, semiflexible gelcaps, as the base, and its pretty corrosive to plastics. Left a couple of the pharmaceutical (heminevrin) capsules on a computer keyboard once, and when I returned to use them, I had to carve them out of the keyboard and rely on removing as much plastic as possible, any sharp edges, and have it come out the other end:D)

Another vote for pyridine also, it has to be one of the foulest things I've encountered.

Also dimethyl trisulfide and disulfide. Awful rotten flesh stink, like a shit covered corpse. And especially the former REALLY carries. 1ppt detection threshold. Its produced naturally by members of the Arum genus of plants, as well as Phalloid fungi.

Smells mercaptan-like, only worse. Ever have a stinkhorn fungus manage to insinuate itself into your home, growing behind the warmth of a refrigerator heat pump? I have. Was in my days as a nipper, presumably either myself or my old man had tracked in some spores, and lo and behold, the thing sprouted, behind our old fridge-freezer growing out of the carpet. Called out the gas repair folk thinking we had a leak, and the repair guy spent quite some time probing for leaks and finding nothing, eventually leaving, without finding anything amiss, quite perplexed.

I just wish he HAD found the culprit, which we found ourselves later on, the look on his face would have been priceless. Won't forget that stench in a hurry. Efficiently vaporised by the warmth of the pump it spread pretty thoroughly throughout the house. If you've ever taken a walk in the woods, and there are Phalloid fungi around, P.impudicus was the guilty party in this case, and fairly common here, they produce a thin layer of tissue that serves as a 'cap' on top of a spongy stalk, and grow out of an egg stage, that if still present, looks like a fungal phallic scatological obscenity. And smells like one too, you'll know its there long before (if) you actually see it.


Edit-forgot acrolein. That has to be even worse than pyridine. Pyridine just packs a vomit-inducing stench, acrolein both smells hideous, acrid, like burning fat. And unfortunately produced by dehydration of glycerine, did so once using bisulfate as the dehydrating agent. The distillation procedure was...unpleasant to say the least. And having a leftover ml or so, a very small quantity was flushed down the sink, and unfortunately flushed with hot, rather than cold water. The resulting fumes coming belching back up the drain were singularly offensive. And the choking fumes that come from commercial e-liquid e-fag refills is due to the glycerine content. I've switched from buying the off the shelf variety to nicotine, propylene glycol and flavouring agent only. With the off the shelf stuff its difficult to take a proper drag unless applying the heat in a pulsed fashion. Or when the tank runs near dry and one doesn't notice, more acrolein. Which really cannot be healthy stuff to inhale on a chronic basis any more than it is pleasant in the short term.

[Edited on 22-1-2017 by tsathoggua1]
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[*] posted on 24-1-2017 at 20:57


Quote: Originally posted by tsathoggua1  
If you've ever taken a walk in the woods, and there are Phalloid fungi around, P.impudicus was the guilty party in this case, and fairly common here, they produce a thin layer of tissue that serves as a 'cap' on top of a spongy stalk, and grow out of an egg stage, that if still present, looks like a fungal phallic scatological obscenity. And smells like one too, you'll know its there long before (if) you actually see it.

Haha love that description. Googled it and they really do look unusually like a- never mind...
As for pyridine, its legendary bad smell didn't make such an impression on me. It wasn't too amine-like either, hard to describe really but not fishy at all like aliphatic amines.
Solvents in general don't smell good to me (apart obviously from the familiar Ethyl Hydroxide!); they seem to have a generic effect, being what they are, of dissolving into and swelling membranes, and inner oily cores of proteins. Beyond a certain level the olfactoceptors down tools and say 'screw chloroform, screw light petroleum, spirits, screw you owner for exposing us to it', and all solvents start to smell the same. Acetone and dichloromethane were alright (but the combination of tiny finger wounds and acetone wash through holey gloves-!).
Ether was strangely worse for trying to smell sweet, but still smelling solventey.
Generally in a lab the presence of solvent is too strong to enjoy them, they create a kind of ...fug.
The worst smell was not however a solvent. It was an unidentified, unspeakable something, that was produced when one of a hotplate's previous users spilled their stuff on it where I couldn't see and it baked when I switched it on. The smell was soft, swollen, vile beyond reason. It, nay - its very existence, was so demoralizing I wanted to cry forever. Corrupted? Yes rather than no. Rotten? Not quite. Neither amine nor organosulfide, it was still almost certainly organic. Maybe triphenylphosphine spilt on it and vaporized from the heat; maybe the oxide of that rearranged to diphenyl phenoxy phosphine. Maybe it was an isonitrile, but they've been described as 'flat' and 'metallic' smelling, so probably not.

Lastly, not my experience but a find of a table which organizes common organic chemicals by scent.
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[*] posted on 26-1-2017 at 12:28


As for ammonia, its (concentrated) smell didn't seem very special, but its chemical impression on the respiratory tract-! I accidentally got a whiff of it from a test tube working of transition metal ammonia complexes in school, and I thought I'd never breathe again :o
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[*] posted on 29-1-2017 at 09:31


Likes: Isopropanol, and SO2(in very low concentrations) and amyl acetate. Sulfuric acid smells like tangy machine oil and i think it smells like chemistry.
I don't care for dichloromethane and while NO2 is noxious and choking I would not say it smells bad.
Dislikes: N-Butanol and amyl alcohol both have a horrible sweat-like smell, also glacial acetic acid frankly smells awful. Funnily enough though I don't mind HCl




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[*] posted on 3-2-2017 at 13:04


I was trying to make isopropyl benzoate by fischer esterification recently and it did not work very well. I got some black tarry crap which smelt like new car and house gas, i even had neighbor come ask if it was me or if there was a gas leak. I ecpecially despise the new car smell so this was not very pleasant for me.

I have no idea what formed though.

My favorite is probably chloroform or piperine.
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[*] posted on 3-2-2017 at 13:57


My favorite day to day smells are ethanol and toluene. Ethanol has a pleasent fruity odor, and toluene's smell reminds me of a garage, which makes me like it for some reason. The best smell that ever came from the lab was when I was boiling down an ascorbic acid solution, an extract from vitamin C pills. It must have been because of impurities, but I can only describe its aroma as delicious. I hate the smell of acetone:mad:. SO2 isn't too bad, and ammonia smells 'fresh' but is suffocating when breathed in. The most disgusting smell ever was when I was cleaning residues of ethyl salicylate from a seporatory funnel with acetone. The two smells mixed together were very unpleasant.
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[*] posted on 6-2-2017 at 04:12


I don't know how anyone could dislike the smell of ether. I dislike the smell of alcohol, preparing to down a mug of spirits is pretty bad, the mental image makes me catch a retch halfway formed, more than the drinking of the beverage itself.

A shot of ether on the other hand triggers no such involuntary shudder, and spirit belches taste terrible too, especially when there is the faint, fruity acetaldehyde smell post-metabolism, but at such a point when both EtOH and acetaldehyde are present.

An ether belch tastes almost as good a when it goes down. Not so pleasant with diisopropyl ether, but still, but too bad in either direction.

(not that I'd drink this in a million years) but EtOAc, the smell of it is just revolting. That sickly sweet fruity smell, its nasty.

I quite like the smell of soldering circuit boards though, brazing using silver-cadmium alloy just doesn't have that same pleasant softness to it, just a slight metallic smell, but lead solder, or molten Pb smells pretty good. Not something I'd want to inhale generally speaking where avoidable, but not unpleasant.

I like the greenish-pale white, wavy smell of CHCl3, and the flat, unmoving white smell of dichloromethane. I'm synaesthetic, mainly in respect of chemicals, although it comes through in other aspects of everyday life too, weirdest thing to try and describe when things like tastes and smells have textures, movements and colors attached to their perception.

And especially, even more than ether, the smell of some of the fluorinated ethers, such as sevoflurane, ether (diethyl) is quite a bit harsher, and whiter than sevoflurane and others very like it, whilst sevo has a sweetness to it, much as nitrous oxide does, which itself, kind of tastes more than smells, but has a nice sweetness to it, and coupled with the 'smell' of the signature of NMDA antagonists, synaesthetically speaking, it just hits a spot somewhere, even though N2O is probably the least favourite of all dissociatives, bar only dextromethorphan which I dislike somewhat, probably due to its noradrenergic and serotonergic effects.

Did I mention acrolein? if I did, it deserves another mention, its just that bad.

And anyone know what gives bubblegum its scent? the classic 'blue bubblegum' flavour used in bubblegum flavour pop and candies?

And whatever it is in 'KA' black grape soda. I'm guessing perhaps an anthranilate ester, I've heard of some of the lower alkyl anthranilates having a black grape soda type scent, although never handled them in person. Although given methyl and possibly ethyl anthranilate are available OTC as bird repellent, that does give one...ideas:D

[Edited on 6-2-2017 by tsathoggua1]
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[*] posted on 6-2-2017 at 04:46


And that eloquent description of the hotplate with something spilled on it and subsequent stench, that really reminds me of thermally cracked 'bromethiazole' or its medically used barbiturate-like (in pharmacological terms, although its a GABAaR agonist at the barbiturate binding site, sans the AMPA type glutamatergic antagonism/ligand trapping of barbs) better known cousin, chlormethiazole.

I tried describing the stench, but ripe, corrupt, that does it. Neither aminey nor sulfurous exactly, not like a lower alkyl sulfide or mercaptan, but sickly, noxious. A little reminiscent of a rotting pus-soaked wound. And a thing which should not be, in a rather lovecraftian kind of way. Absolutely sickening even in traces (such a twice-washed sep funnel, that was enough to drive me from the room and not re-enter for days without a respirator and organic cartridges fitted.)

I imagine the vitamin B1-derived intermediate, thiazole-2-ethanol would be pretty bad if thermally cracked too, easily made by bisulfite/metabisulfite cleavage of the thiamine, vitamin B1. I am not about to try it though, I have absolutely no desire ever to encounter that unspeakable abomination of a stench ever again, nor anything like it. Its extraction in CH2Cl2 for chlormethiazole/bromethiazole syntheses in future.

No idea what the iodo homolog smells like when burnt, but a terminal iodoalkane is not something I'd want in a sedative-hypnotic, bromo is pushing it a bit, the iodinated version, thats too good a leaving group and potential/probable alkylating agent for me to waste the time, and the thiazole-2-ethanol that could go into making a perfectly good sedative-hypnotic and a top-up for the rx I have for the chloro derivative, for those times I need to use some in an acute situation during the onset of a seizure, to prevent it progressing so as not to be left without the requisite daily quantity as a prophylactic.


A question-does elemental tellurium smell awful? because I've been after some, specifically, native Te on sylvanite. Ever seen the photo of Theodore Gray's piece? I'd go so far as to say its of gemstone quality, quite beautiful, albeit not suitable for adornment, for obvious reasons.

This is, not when heated, but simply as a display piece? assuming the right piece can be obtained, at room temperature and in its elemental state?

I should add, butyric acid, and propionyl chloride. Have been using both a bit lately, and a certain dipropionyl ester of a certain morphinan is, rather a favourite amongst organic compounds, but propionyl chloride, the HCl aside, as well as the carboxylic acid itself smells distinctly 'goaty' with overtones of sweaty armpit. This is referring to propionyl chloride and propionic acid. Butyric acid has been formed as a byproduct of using the anhydride, and its rancid and sticks around for days. Get the least bit on you, and again it follows you around like flies follow shite. Rancid dairy kind of stink, only hollower. Echoey. But that bit probably won't make sense to any nose but mine.

[Edited on 6-2-2017 by tsathoggua1]
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[*] posted on 6-2-2017 at 20:50


Quote: Originally posted by tsathoggua1  
At least going down. Not so bad coming back up post belching after ingestion of the drug in capsule form


Worst-tasting pill burp: cephalexin, hands-down




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[*] posted on 6-2-2017 at 21:04


Cephalexin itself doesn't have a smell (at least, we used a concentrated stock solution in one of my lab classes, and I didn't notice any smell). Maybe it was some sort of excipient that had the smell?



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[*] posted on 7-2-2017 at 06:55


Likes:
Acetone: very sweet like candy smell
Bleach: Just smells ultra clean
Sulfuric acid: smells a bit like oil.

Dislikes:
Ammonia: Even in low concentrations i've always hated the smell
All carboxylic acids, the worst being Butric in my opinion.
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[*] posted on 7-2-2017 at 09:03


Quote: Originally posted by Σldritch  
I was trying to make isopropyl benzoate by fischer esterification recently and it did not work very well. I got some black tarry crap which smelt like new car and house gas, i even had neighbor come ask if it was me or if there was a gas leak. I ecpecially despise the new car smell so this was not very pleasant for me.

I have no idea what formed though.


I've encountered the same thing when preparing isopropyl salicylate by two methods. The first was a traditional Fischer but the second was a transesterification starting from methyl salicylate. In the second synthesis there was a lot less tarry crap and I actually got a gray organic layer to separate out, but it smelled exactly the same! To date it's one of the only times chemistry has made me gag.
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[*] posted on 7-2-2017 at 10:25


Quote: Originally posted by Metacelsus  
Cephalexin itself doesn't have a smell (at least, we used a concentrated stock solution in one of my lab classes, and I didn't notice any smell). Maybe it was some sort of excipient that had the smell?


I think what happened was the gelcap dissolved but the powder inside didn't get wetted immediately, became aerosolized, and wafted up into my nose and mouth.

In the unknown-but-rank category, wayyy back in 2013 when I was first getting back into home chem, I was trying to make chromium sulfate from chromium metal and sulfuric acid. As I was heating the solution down, I decided to add IPA for reasons that I've since forgotten. What I definitely remember was the oily purple liquid that formed on top and the suffocating odor, like hot asphalt but also rotten. I still wonder sometimes what happened, but the smell (and possible toxicity) has kept me from a controlled replication.

[Edited on 7-2-2017 by mayko]




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[*] posted on 8-2-2017 at 15:03


A chromate ester perhaps? oxidation/dehydration to an aldol, since several chromium-based oxidants, such as CrO2Cl2, PCC etc, and esterification? like a hybrid Etard/esterification ?

Do enals form esters like enols?

[Edited on 8-2-2017 by tsathoggua1]
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[*] posted on 25-2-2017 at 15:30


Having just made disulphur dichloride I would definitely put this on my list of least favorite smells. "horrific" is about the only way I can describe it.

Likes

.Ethyl benzyl ether (citrus pineapple)
.Diethyl oxalate (ethereal, grape like)
.Tert-butyl chloride
.limonene
.chloroform

Dislikes

.Isopropylamine (fishy ammoniacal, but smells more natural then ammonia)
.methylamine (fishy ammoniacal)
.disulphur dichloride
.Chloramine
.Toluene
.benzyl chloride




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[*] posted on 26-2-2017 at 11:21


long term exposure to Kerosense made me sick, and Xylene is the same but not quite as nauseating. The harshest chem ive ever breathed was propionyl chloride, never again will i handle that without a respirator.

On the other hand i LOVE the smell of Vinegar, or dilute acetic acid.
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[*] posted on 19-3-2017 at 10:16


Quote: Originally posted by tsathoggua1  

And anyone know what gives bubblegum its scent? the classic 'blue bubblegum' flavour used in bubblegum flavour pop and candies?
[Edited on 6-2-2017 by tsathoggua1]


Bubble gum flavor is is a mix of ethyl methylphenylglycidate(strawberry) and isopentyl acetate(banana)




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[*] posted on 19-3-2017 at 11:01


i LOVE the smell of Vinegar, something about a 5% acetic acid solution is just very sweet! but GAA is too much. Ive heard Pyridine stinks to hell And i HATE the smell of Ether.
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[*] posted on 19-3-2017 at 12:17


I have begun to hate the smell of pyrrolidine after doing some work with it, this is really stinking bad.

Best smelling chemical, hmm... I like l-carvone´s smell, geraniol, nerol and similar substances are appealing for my nose too.
Oh, and syringol is also very nice, has the smell of aromatic smoke and a little sweet component too, reminiscent of vanillin.

@tsathoggua: I don´t know which kind of bubblegum exactly you mean, but l-carvone is in quite a few(mint-like ones) the dominant aroma compound.
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[*] posted on 19-3-2017 at 20:26


I started loving the smell of ammonia after a recent accident in my lab ...

Has anyone here smelled a fresh culture of Pseudomonas aeruginosa? The smell its ... weird, it's like fruity but at the same time wet ... like when wood gets moldy but more fruity ... After that you start sensing that smell everywhere, it's quite annoying
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[*] posted on 19-3-2017 at 20:42


also safrole smells great i miss that smell
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[*] posted on 23-3-2017 at 04:25


I haven't done anything that bad except for spilling a whole bag of 95% pure sulfur powder all over the ground.



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[*] posted on 16-4-2017 at 10:43


Not sure how anyone could hate the smell of ether. Acetic acid is just nasty.

Don't mind propionyl chloride too much. But the aftertaste that lingers after working with it from even the smallest amounts is foul. The halide is alright but the free acid is vile.
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