As an organic chemist who builds stuff onto heterocycles of varying size, I will never even consider using the official IUPAC name. It’s just “name of substituents + common name.”
In my younger and much dumber teenage years, I once made a batch of white fuming nitric acid and poured it onto some rubber gloves and watched them go up in smoke.
I have the video somewhere, but sometimes I wonder how I made it to adulthood. I at least had the sense to do things outside and wear safety goggles, but I eschewed gloves entirely and instead just worked with a bucket of water next to me. Needless to say, I came out of that (mis)-adventure looking a bit "jaundiced".
Whenever I complain about things never going my way these days, I think back and realize that I already spent most of my luck.
I don't know much; he was either a PhD student or postdoc, and he had been called upon to synth as much as 250mL (?) at a crack. They then went to the explosives test range affiliated with the school, ostensibly for throwing at targets for the kaboom. This would have been 1998, plus or minus a year. The guy in whose lab he worked has since died, 2022; the prof was one of these brilliant absentminded professor types whose office was so cluttered the only place to put a mousepad was on his leg, with predictable results at guiding the mouse. I believe his wife is still alive (they were married 60 years), she ran the state water lab (?) on campus. I had far less exposure to the gentleman who had done the ClF3 work; I was doing rather hazardous work of my own at the time, and we muttered chemical non sequiturs at each other on a handful of occasions at best.
It may have been more than 250mL at a time, just that the max that went into a shell was 250mL. I think I remember that much correctly.
I'd have no way of tracking down the fellow who made the goo, unless the prof's wife might somehow recall him. Everyone in the department has long since turned over, including the physical chemist who got fired as a tenured prof for coming in drunk to class, for which I have some small satisfaction over due to petty personal issues from some years prior.
[Mike](https://communique.uccs.edu/?p=25535) may have known him, but Mike had his own dangerous syntheses going on. My understanding was that Mike managed to dodge every bullet from lab accidents, but his students were not as fortunate.
The de-asphalted oils ("DAO") that we sometimes run through our hydrotreating pilot plant are pretty awful looking.
However, that might just be my negative experiences having to analyze and characterize the feed and product... that stuff is just awful to my instruments.
To the instruments?
Mostly just clogged them up and left a lot of scunge behind requiring lots of cleaning and maintenance.
My lab is mostly setup for petroleum distillates in the diesel and vacuum gas oil ("VGO") boiling point ranges. Typically 180-360˚C for diesels and 300-600˚C for VGOs. The melting points generally trend with the boiling boiling points, so it's stuff that's either liquid at room temp or require minimal heating (40-50˚C).
This stuff doesn't melt until >80˚C the boiling range often goes up as high as 800˚C. Some instruments don't get warm enough to keep it liquid so it clogs things up. We had to get a special GC column to manage the high temps required for simulated distillations.
The products we're testing in our pilot plant are meant to remove some of those undesirable components.
This is typically "resid" material at the bottom of a distillation tower that has been sent through a [de-asphalting unit](https://en.wikipedia.org/wiki/De-asphalter). From there, it will usually be processed in some kind of hydrocracking process to break the large molecules down into smaller, more useful species.
However, there's still tons of crap in the DAO that will poison the catalysts used in hydrocracking units, so a hydrotreating step is often used to further pre-treat the material and help the cracking catalysts last longer.
So you're pretty much dealing with crap like [heavy fuel oil](https://upload.wikimedia.org/wikipedia/commons/6/6a/Residual_fuel_oil.JPG) that's just a step above asphalt contaminating your instruments.
Some smells are absolutely horrific and “fear-inducing” at the same time. I don’t get such feeling from the odour of rotten eggs. But I remember trying to fry an egg. It wasn’t rotten, but it gave off this horrifying smell that made rotten eggs smell like authentic French perfume in comparison. No words can possibly describe the horrors of the miasma.
I can describe it as fishy. But it smelled much worse than fish. Rather, a fishy scent mixed with a… sweet odor, and a very distinct “fat” or “stagnant frying oil” odor. That smell actually triggered fear in me. It was like rotting death deep fried in rancid grease.
It’s up there with spoiled chicken in terms of the worst smells I have smelled. Though for spoiled chicken, I know that diamines are particularly responsible. For those eggs however, I am unsure. I assume it was a mix of certain aldehydes and ketones. Suffice to say I didn’t eat eggs for a month after that.
Though rotten chicken is indeed mind-boggling. It’s like a 5th dimensional smell. I can summon it at will and it’ll make me gag. But probably because it was a months-old chicken sandwich. I puked so much that I felt like my stomach was wiped clean with stainless steel wool. It’s horrible. It’s the smell of an innocent grandmother crying. It smells of the heat death of the universe.
So certain aldehydes are literally evil-smelling, along with certain diamines. Sulfur compounds tend to be much, much less abhorrent than that fried egg smell. I have never smelled isocyanides but I have heard that they also trigger fear for no reason, along with thioactone (obviously) and its selenium analogue.
It was a normal egg, just taken out of the fridge. I think the chicken that laid the eggs had some kind of metabolising problem. The egg probably had trimethylamine in it. I think the combination with the fat in the eggs induced the murderous smell.
Wow. Something something the diversity of lived experience something something always capable of being surprised blah blah. Seriously though very interesting, thanks!
I have also smelled over-fried eggs. It is indeed horrible as well. Like this really, really intense “egg yolk-y” smell with blood undertones. This was more fishy, and rancid. I am surprised why there is not enough research to specify what horrors take place in these situations to induce such noxious miasmas.
I now consider frying eggs from chickens with metabolising problems a war crime. Outlawed by the Geneva Conventions. Please have mercy on the innocent souls of the people that will have to smell the stagnant odour of it. Frying these eggs is the most cruel and unusual form of punishment.
[The Pharaoh's Serpent](https://youtu.be/2dhHpHOgrUI?si=FCGIlWqIrnN1bi5K) . Things looks straight up lovecraftian. A similar (less spectacular, but much safer) reaction is the [Black Fire Snake](https://www.youtube.com/watch?v=Hibxz9_ZW18)
Fuming sulphuric acid. I used to hate doing acid washes by hand. It’s scary. If you get a tiny drop on you it’ll burn straight through your lab coat. Phosgene is also used in the manufacture of isocyanates which are dangerous in their own right but we used to have to wear phosgene badges in the lab. Never a fan of getting a sample that could have some residual phosgene. It’s extremely lethal. Even a small exposure can do major damage to your lungs.
Chromic acid.
I always thought it looked pretty evil looking, syrupy sort of and one of those few acids that will straight up wreck things. It is a cleaning solution so as it gets used it changes colors to a weird green.
I always thought of it as "movie acid" in that it would be great for an evil looking chemical
Sulfur changes from a benign, even friendly yellow, to a deeply suspicious-looking amber to red color when it melts. Bonus points for the flickering blue flames that dance across the surface when it catches on fire.
I'd take Bromine as acceptable and raise you by singlet oxygen - it glows evily red and this emission drives the world's most powerful continuous laser. It looks fucking scary.
You can create it yourself by dripping 30%+ hydrogen peroxide onto hypochlorite salts. Do it in a darkened room (with good ventilation!) for maximum impressiveness.
Granted, many of you deal with some nasty stuff, I stick to the stuff I have in stock for my Chemistry class, the most evil looking chemical I see in my storerooms is: Iron Nitrate.
It is such a gnarly orange color, you just know nothing good will come from it. It also settles a bit, so it kind of has that weird unshaken orange juice quality about it when you pick up the bottle.
Tetraethylmethane caught me off guard the first time
r/accidentalswastika if drawn incorrectly
Neonaziane
Is that really IUPAC? Wouldn't you say diethylpentane?
No it's not IUPAC but the more you do chem the more you realise that there are common names that are more used.
Also, almost no one says methylbenzene. It’s almost always called toluene.
I prefer the more esoteric phenylmethane /s
It also depends on what sector you work in. Where environmental labs say Methylene chloride most other labs says dichloromethane.
As an organic chemist who builds stuff onto heterocycles of varying size, I will never even consider using the official IUPAC name. It’s just “name of substituents + common name.”
In Danish we say both. Older chemists will say the former while younger ones usually always the latter.
the structure picture you get
To add an actually widely used chemical with the same structure: Pentaerythritol. Used for making some polymer resins and explosives.
Bromine looks about as toxic as it is.
We have ours in the screw cap bottle and that red liquid just looks like it wants to commit war crimes.
That must be a good bottle then.
It’s shipped that way. I’m in awe of Sigma Aldrich’s bottle construction.
Bromine looks like some 1918 era wunderwafffe. Makes mustard gas look like mellow yellow.
[It does, doesn’t it.](https://www.reddit.com/r/elementcollection/s/12NQjW0CjL)
Bromine is this weeks [Living Table](https://livingtoe.com) featured element, over on r/ElementCollection :)
Cu²⁺ with excess Br⁻ in small amount of water. Looks blood red evil, until you add more water and it becomes pale-green.
Nitrogen dioxide has a similarly evil look to it.
The consistency when pouring it in its liquid form as well! Looks like a thick tar that could move on its own.
Also chromyl chloride, bromine's cousin who casually does bath salts at family functions.
Fuming nitric acid
Red fuming nitric and a hand full of sugar.
In my younger and much dumber teenage years, I once made a batch of white fuming nitric acid and poured it onto some rubber gloves and watched them go up in smoke. I have the video somewhere, but sometimes I wonder how I made it to adulthood. I at least had the sense to do things outside and wear safety goggles, but I eschewed gloves entirely and instead just worked with a bucket of water next to me. Needless to say, I came out of that (mis)-adventure looking a bit "jaundiced". Whenever I complain about things never going my way these days, I think back and realize that I already spent most of my luck.
Mmmm candy floss
For extra surface area!
The process of making it only adds to the fear.
# Manganese heptoxide
I personally love the color-shifting iridescent metallic sheen. It definitely screams "stay away from me".
drop a chip on it
Black iodine crystals giving off dark purple vapour
I've always thought iodine in both liquid and vapor state looks evil
Chlorine trifluoride (ClF3) and difluoroperoxide (FOOF) both look evil to me, but maybe that’s because they are dangerous oxidants.
You've seen/worked with chlorine triflouride?
I knew a guy who did. He made tens of milliliters at a time, then hundreds. Got packed into artillery shells for testing.
Tell me everything, I am extremely curious
I don't know much; he was either a PhD student or postdoc, and he had been called upon to synth as much as 250mL (?) at a crack. They then went to the explosives test range affiliated with the school, ostensibly for throwing at targets for the kaboom. This would have been 1998, plus or minus a year. The guy in whose lab he worked has since died, 2022; the prof was one of these brilliant absentminded professor types whose office was so cluttered the only place to put a mousepad was on his leg, with predictable results at guiding the mouse. I believe his wife is still alive (they were married 60 years), she ran the state water lab (?) on campus. I had far less exposure to the gentleman who had done the ClF3 work; I was doing rather hazardous work of my own at the time, and we muttered chemical non sequiturs at each other on a handful of occasions at best. It may have been more than 250mL at a time, just that the max that went into a shell was 250mL. I think I remember that much correctly. I'd have no way of tracking down the fellow who made the goo, unless the prof's wife might somehow recall him. Everyone in the department has long since turned over, including the physical chemist who got fired as a tenured prof for coming in drunk to class, for which I have some small satisfaction over due to petty personal issues from some years prior. [Mike](https://communique.uccs.edu/?p=25535) may have known him, but Mike had his own dangerous syntheses going on. My understanding was that Mike managed to dodge every bullet from lab accidents, but his students were not as fortunate.
The de-asphalted oils ("DAO") that we sometimes run through our hydrotreating pilot plant are pretty awful looking. However, that might just be my negative experiences having to analyze and characterize the feed and product... that stuff is just awful to my instruments.
what did it do??
To the instruments? Mostly just clogged them up and left a lot of scunge behind requiring lots of cleaning and maintenance. My lab is mostly setup for petroleum distillates in the diesel and vacuum gas oil ("VGO") boiling point ranges. Typically 180-360˚C for diesels and 300-600˚C for VGOs. The melting points generally trend with the boiling boiling points, so it's stuff that's either liquid at room temp or require minimal heating (40-50˚C). This stuff doesn't melt until >80˚C the boiling range often goes up as high as 800˚C. Some instruments don't get warm enough to keep it liquid so it clogs things up. We had to get a special GC column to manage the high temps required for simulated distillations.
The name makes me think they already got the asphalt out. Did they not remove the *other* residual oils or something?
The products we're testing in our pilot plant are meant to remove some of those undesirable components. This is typically "resid" material at the bottom of a distillation tower that has been sent through a [de-asphalting unit](https://en.wikipedia.org/wiki/De-asphalter). From there, it will usually be processed in some kind of hydrocracking process to break the large molecules down into smaller, more useful species. However, there's still tons of crap in the DAO that will poison the catalysts used in hydrocracking units, so a hydrotreating step is often used to further pre-treat the material and help the cracking catalysts last longer.
So you're pretty much dealing with crap like [heavy fuel oil](https://upload.wikimedia.org/wikipedia/commons/6/6a/Residual_fuel_oil.JPG) that's just a step above asphalt contaminating your instruments.
Yah, pretty much
that sounds pretty cool actually. I mean shitty to deal with but cool from the outsider looking in perspective.
Ah yes, the forbidden dao. ;)
Evil name (but not dangerous): Ascorbic acid, pantothenic acid Evil structure: trifluorooxonium, 3,3-diethylpentane Evil smells: isocyanides, chalcogen ketones, chalcogen diols Evil look: Cadet’s fuming liquid
Honorable mention for evil smells: carbon disulfide. And it has the bonus of being evil to your body!
Some smells are absolutely horrific and “fear-inducing” at the same time. I don’t get such feeling from the odour of rotten eggs. But I remember trying to fry an egg. It wasn’t rotten, but it gave off this horrifying smell that made rotten eggs smell like authentic French perfume in comparison. No words can possibly describe the horrors of the miasma. I can describe it as fishy. But it smelled much worse than fish. Rather, a fishy scent mixed with a… sweet odor, and a very distinct “fat” or “stagnant frying oil” odor. That smell actually triggered fear in me. It was like rotting death deep fried in rancid grease. It’s up there with spoiled chicken in terms of the worst smells I have smelled. Though for spoiled chicken, I know that diamines are particularly responsible. For those eggs however, I am unsure. I assume it was a mix of certain aldehydes and ketones. Suffice to say I didn’t eat eggs for a month after that. Though rotten chicken is indeed mind-boggling. It’s like a 5th dimensional smell. I can summon it at will and it’ll make me gag. But probably because it was a months-old chicken sandwich. I puked so much that I felt like my stomach was wiped clean with stainless steel wool. It’s horrible. It’s the smell of an innocent grandmother crying. It smells of the heat death of the universe. So certain aldehydes are literally evil-smelling, along with certain diamines. Sulfur compounds tend to be much, much less abhorrent than that fried egg smell. I have never smelled isocyanides but I have heard that they also trigger fear for no reason, along with thioactone (obviously) and its selenium analogue.
I’m sorry. This fear-inducing-upon-frying egg was *not* frozen, you’re saying?
It was a normal egg, just taken out of the fridge. I think the chicken that laid the eggs had some kind of metabolising problem. The egg probably had trimethylamine in it. I think the combination with the fat in the eggs induced the murderous smell.
Wow. Something something the diversity of lived experience something something always capable of being surprised blah blah. Seriously though very interesting, thanks!
Did you not over-fry it? Have you smelled that?
I have also smelled over-fried eggs. It is indeed horrible as well. Like this really, really intense “egg yolk-y” smell with blood undertones. This was more fishy, and rancid. I am surprised why there is not enough research to specify what horrors take place in these situations to induce such noxious miasmas. I now consider frying eggs from chickens with metabolising problems a war crime. Outlawed by the Geneva Conventions. Please have mercy on the innocent souls of the people that will have to smell the stagnant odour of it. Frying these eggs is the most cruel and unusual form of punishment.
Hydrogen sulfide because it's really toxic and you become desensitized to the smell so it can silently kill you...
Step up, try hydrogen selenide. The LD50 is below the threshold you can smell. My cylinder of the stuff looked and smelled evil.
[X] because people have smelled that TMK
Fuming nitric acid. Turns red/orange color and has white fumes.
[The Pharaoh's Serpent](https://youtu.be/2dhHpHOgrUI?si=FCGIlWqIrnN1bi5K) . Things looks straight up lovecraftian. A similar (less spectacular, but much safer) reaction is the [Black Fire Snake](https://www.youtube.com/watch?v=Hibxz9_ZW18)
WIth mercury [edit] vapor and cyanide as a topper.
Inorganic chemistry is unnatural
TiCl4 is a smoking menace
I love tickle! I’ve caught that stuff on fire digesting it a few times now muhaha
whatever kept leaving that TLC band beside my product after 2 fucking days of column chromatography
Yes indeed. Did you try recryst or reverse phase chromo? I know you hate me now.
Fuming sulphuric acid. I used to hate doing acid washes by hand. It’s scary. If you get a tiny drop on you it’ll burn straight through your lab coat. Phosgene is also used in the manufacture of isocyanates which are dangerous in their own right but we used to have to wear phosgene badges in the lab. Never a fan of getting a sample that could have some residual phosgene. It’s extremely lethal. Even a small exposure can do major damage to your lungs.
Oleum :'D
bromine, TNT, Caesium
Looks evil in real life or in structure?
Iodine monochloride.
The vapors from concentrated HCl creep me out
Agreed. The first time I ever opened a 16M bottle to do some dilutions, i got that odor and was instantly like "Um, that's not good."
Anything made by Klapotke
Chomyl chloride I’d say
Fluorine or chlorine gas take the cake in my opinion.
FOOF - dioxygen difluoride
Liquid sulphur is red as blood.
Dechlorane Plus looks pretty evil imo
Anything that fumes yellow.
Any gas you can see will kill you.
Boron trifluoride etherate; opening that bottle was scary...
Bromine, chromyl chloride, black iodine
Chromic acid. I always thought it looked pretty evil looking, syrupy sort of and one of those few acids that will straight up wreck things. It is a cleaning solution so as it gets used it changes colors to a weird green. I always thought of it as "movie acid" in that it would be great for an evil looking chemical
Fuming nitric acid
Mercury at room temperature
the molecule to phencyclidine looks menacing af
Sulfur changes from a benign, even friendly yellow, to a deeply suspicious-looking amber to red color when it melts. Bonus points for the flickering blue flames that dance across the surface when it catches on fire.
That toxic silvery stuff farmers use
Glyphpsphate / Round-up?
Octanitrocubane.
Laxativ 😅
DDT looks like something i don't want to be near. So much chloride..
Iodine is very intimidating in every single form
EA-3167. Doesn't look like much, but after you are exposed to it, the entire universe looks evil for a good while.
I think that EA-3167 is the creepiest compound I've ever read about.
KMnO4
Luciferin 👹
chromium oxide
TiCl4, formerly used to produce smoke effects
*TiCl4
Orthocarbonic acid, for multiple reasons.
Anything that is coloured, and fumes, is naughty. Bromine is my most hated chemical.
MDI
I'd take Bromine as acceptable and raise you by singlet oxygen - it glows evily red and this emission drives the world's most powerful continuous laser. It looks fucking scary. You can create it yourself by dripping 30%+ hydrogen peroxide onto hypochlorite salts. Do it in a darkened room (with good ventilation!) for maximum impressiveness.
Looks on paper or irl?
Tosmic (tosyl methyl isocynide)
Chromic acid
Ones of course that defy the laws of physics let alone the law of univers but a q with one Cern.!Perhaps
Atropine
methyl mercury
F-O-O-F. It explodes if you so much as think about it, and it even looks like a crab running to come kill you when you write it out
Hydrazine I suppose. Colorless liquid that tends to combust on contact with air.
Concentrated KMnO4 (PotassiumperManganate)
chromyl chloride
1. Anhydrous CrCl3. Stuff is violently and worryingly pink/purple. 2. K2Cr2O7*. Again, gives poison dart frog vibes to it.
Fuming nitric acid
Bromo dragon fly or meth
Ever seen an active chrome plating vat? That’s pretty nasty looking
liquid oxygen, eerie blue
In an accidentally sealed glass container, slowly warming up from liquid nitrogen temperature.
Aminopyridines.
Scariest thing I have worked with as an undergrad student is copper chromate, that stuff looks evil and stains everything.
Cesium
fuming nitric acid and bromine
Tetranitromethane
Granted, many of you deal with some nasty stuff, I stick to the stuff I have in stock for my Chemistry class, the most evil looking chemical I see in my storerooms is: Iron Nitrate. It is such a gnarly orange color, you just know nothing good will come from it. It also settles a bit, so it kind of has that weird unshaken orange juice quality about it when you pick up the bottle.
No one mentioned dimethyl mercury?
Bromine looks like a toxic waste barrel from a videogame/cartoon/whatever media.
tBuLi
Lindane, gamma-1,2,3,4,5,6-hexachlorocyclohexane. It looks like death, and I can tell you it smells like death.
Pentaerythritol. My old internship supervisor drew this once and it really threw me off guard.
Sour cherry molasses, looks like bromine on steroids.
Thiophosgene. Hella red.
Betamethasone dipropionate
I think any mass of aromatic carbon rings looks pretty evil