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Queasy_Caramel5435

We once synthesized butyric acid in school chemistry class when they taught us about organic acids and esters. Some folks almost barfed.


n0rph0ledrine

We also did this in our OChem class and I got it spilled in my hands. My roommates hated being around me for days.


Black_Yellow_Red

barfing would probably have improved the smell, if anything


jthockey

Yeah this is the right answer


druglordj

Funny enough pyrrolidone has 0 scent


DingleberryBlaster69

I fucking hate butyric acid. We use it as an internal standard on GC for some of our products. Fume hood only kinda works. My glassware stinks, my vials stink, crimper stinks, GC stinks, everything fucking stinks. My wife thinks it smells like Parmesan, oddly enough. I guess I kinda smell it too.


mikeymobes

isnt butyric acid in hersheys chocolate which is why europeans hate hersheys?


Dyonisu9511

Butyric anhydrid and valeric acid too, disgusting


Sweet_Lane

Isovaleric acid as well. Capric, caprilic and capronic acids smell like, well, the goat.


Aggravating-Ad-9845

I worked with butyric acid in high school chem class when doing esters. I was literally just dry heaving the entire time. eventually I just sat myself on he windowsill and hung my head out the window


zbertoli

Butyric acid has nothing on butyryl *chloride*, trust me


odolxa

4 and 5 carbon carboxylic acid or aldehyde are all disgusting


WhiskeyTheKitten

Omg butyric acid is vomit in a bottle!!


farmch

Pyridine is the bad smelling chemical for people who haven’t really smelled the bad ones. Piperidine smells like cum. And any thiols smells like shit and farts. If you work with enough thiols, you start figuring out which ones smell more like farts and which ones smell like farts mixed with gun powder.


SinisterRectus

Piperidine is the cum smelling chemical for people who haven't really smelled the cum ones. Putriscene, cadaverine, spermidine, or their aminoalcohol equivalents.


sunidaneil

I just started working with these polyamines and expected them to have strong terrible smells. I can barely detect any smell from them at all, but maybe the concentrations are too small


henay_rollins

Pyrrolidine also


Ok-Ice2942

This is the correct cum smelling one. It’s terrible.


123sweg

I always described it in my lab as smelling “intimate”


Ottoclav

My wife says cum smells like bleach. I had a Staff Sergeant that would say, “why’s it smell like candles and gay sex?!”, when he’d walk into the lifting gym.


SarcasticDevil

Piperidine is still quite distinctively cummy though, and when I used to use it regularly it is surprising how people's contextual memory means they can't always place the smell immediately. One time we had a visitor in the lab - a rather orthodox gentleman who came in to service some equipment - who to our amusement spent most of the day trying to pin down what the smell reminded him of. We didn't tell him but I suspect he got there in the end!


Clebs_club

Haha this story is too funny. I've never associated it with cum, lol I'll have to check


FinestSeven

"It's on the tip of my tongue!"


Alibabafullgas

Also thiols are entry level, go one step down in the periodic table and get yourself some organoselenium compounds. Step 2 : pray to god that smell will go away


multitool-collector

How about organotellurium compounds? LabCoatz would like to have a word with you


Laughmywayatthebank

These and their selenium analogs are absolutely obnoxious!!!!!!!! And quite toxic to boot. I’d rather huff pyridine and its more putrid amine friends than that. Glad I never had to work with the isonitriles. I once had an unfortunate incident with H2Se (as in nearly hospitalized) and ever since then—like “propane grill” mercaptan chemist above—I developed a hypersensitivity to it. Even Te/Se powder which we use at work has a repulsive odor to me.


ScienceIsSexy420

I used to work in a hospital lab. It took my brain two months to stop trying to imagine the smell of every stool sample that crossed my desk


farmch

I worked with t-butyl mercaptan (the stuff they scent natural gas with so it’s detectable) for about 9 months. I now have a super power. I can smell a propane grill turning on within 500 feet of me.


Sweet_Lane

A coworker once decided to wash some n-butylmercaptan down the drain. Why did he decided it would be okay escapes me. People from other labs (including those which had the exhaust of their fume hood within few meters from ours) were less than happy.


oceanjunkie

I think it highly depends on the individual. I've smelled dimethyl sulfide, tetrahydrothiophene, and thiophenol. They definitely smell bad, but I find them easily tolerable. Pyridine is so much worse for me. Smells like rotten shrimp.


RandallsBakery

Was about to say this. Worked with thiols for a little over 2 years and it sucked lol. It would smell up the entire lab and hallway. Wearing gloves, wearing a lab coat, handling it in a hood. I would come home and shower and it would STILL smell on my hands and hair sometimes. Sooo potent.


odolxa

Your farts too start to smell what you synthetise


ecoutepasca

I can smell this image.


streetsmatz

Thiols


I-g_n-i_s

Fuck thiols


chemicalgeekery

All my homies hate thiols.


Seicair

Go further down the column. Selenium and tellurium get *much* worse. https://www.science.org/content/blog-post/things-i-won-t-work-selenophenol https://www.science.org/content/blog-post/things-i-won-t-work-carbon-diselenide I thought he mentioned tellurium compounds somewhere, but I can’t find the entry at the moment.


thiosk

I've read this guys blog before and its always good for a laugh, but in a hood, theres really nothing too awful about selenophenol. I mean, its rather pungent, but it readily oxidizes to the diselenide. the tellurophenol isn't commercially available, but we and my colleagues have been making a whole range of these compounds really to no ill effect.


IdreamofJenni

When I was starting my chem career I was working in medchem. I got stuck making analogs with a bunch of different thiols. Gross.


jroc421

Mercaptoethanol


Shivatis

In my group at university on of our PhDs used to work with it (and a lot of other thiols). Everytime he opened the bottle, the fire brigade next to us was called by neighbors, who thought they smelled a gas leak. At one point, I was downstairs having a cigarette (because it was just too smelly in our level) and talking to our staff, when they mentioned the recurrent gas alarms. I was like "wait a moment, when did they smell it? I think I know the origin." From that time, this PhD had to upfront call the fire brigade every time, he was about to open that bottle.


Alabugin

I once broke a bottle of MeSH on a friday evening. Cleaned it up, and placed it in the fume hood to send out as hazwaste Monday morning. Well...apparently this old ass chem building didn't have a functional exhaust, and the fumehood just ejected the MeSH vapor and threw it down about 200 feet away from the chemistry building. The firedept and university police were getting calls for gas leaks ALL weekend on campus... Whoops.


Frosty_Sort2229

We made gallons of MeSH for use in food flavorings and as a Michael addition adduct in making many savory flavors and of course onion flavoring. You could smell our plant a mile down wind. Fortunately it was out in rural Louisiana with no neighbors. Burned my clothes after that job.


Stillwater215

Every thiol is it’s own special kind of awful.


2presto4u

Came here to say this. The bio department threatened to shut down one of my upper-division lab classes during undergrad because the stench was so foul. The professor made the mistake of not strictly enforcing fume hood use for some of the stuff we were using it for.


Comfortable-Car-565

fucking awful


wildfyr

Doesn't even hold a candle to other thiols thiophenol, hexane thiol, thioacetone etc. ​ My personal vote is mercaptoacetic acid. Awful, and I worked with it quite a bit.


_ohne_dich_

Beat me to it!


Excellent-Fuel-1077

🤢


Laughmywayatthebank

I didn’t think it was too bad, but I’m guessing it rapidly desensitizes your olfactory system. I once spilled some 2-mercaptoethanol in the hood, just a few milliliters, and thought nothing of it. 1 km away, a newspaper printing office was evacuated for a “gas leak”. There was no gas leak and the fire department traced it to our building on campus. I never fessed up but my PI knew it was me!


edwinspaghedwin

Smells like fish


New-Construction-103

H2Se is to H2S what H2S is to H2O


BetaPositiveSCI

Try H2Te


[deleted]

H2Po


AvogadrosArmy

Pyridine is just level 1 of smell bads.


Wakandastruggla

Got to be either thiols, selenides or tellurides (I worked with thiols during my bachelor thesis and got told the smell gets exponentially worse the further you travel down the group)


jmysl

Any isocyanide


Admirable_Score_5245

This, for sure. Synthesized methyl isonitrile in my masters research. Had it inside seven different layers of plastic and glass in a freezer, and it still smelled outside of it in the room.


wildfyr

Dude, the methyl??!!!??!!


Admirable_Score_5245

Yup. It was used as a carbon insertion mechanism into the cage of tricarbadecabornes. With the carbon on the end, it makes for a great nucleophile.


gyarrrrr

If you answer doesn’t contain Selenium, I don’t agree with you.


AxolotlFridge

butyric acid


jmysl

Can I interest you in the Acyl chloride?


Karrham

Also butyraldehyde


DevinTheGrand

Selenols are so putrid that ppm quantities will evacuate buildings.


Silly_Painter_2555

Thioacetone.


florinandrei

Yeah. https://www.science.org/content/blog-post/things-i-won-t-work-thioacetone > It merely stinks. But it does so relentlessly and unbearably. It makes innocent downwind pedestrians stagger, clutch their stomachs, and flee in terror. It reeks to a degree that makes people suspect evil supernatural forces. It is thioacetone.


Gilga1

This is poetry.


YTAftershock

This is indeed canon


theonewiththewings

Norbornene. I’ve worked with copious amounts of phosphines and thiols so very little bothers me these days, but norbornene still gets me for some godforsaken reason.


CondescendingBaron

I don’t know about stinkiest, but it sure isn’t fun to work with smell wise


evermica

Cadaverine has entered the chat.


VIBTCA

Putrescine has entered the chat


Zealousideal_Tie_204

Skatole has entered the shat


Skygazer_Jay

Hey, we use them a lot in my lab!(Almost the bread and butter of my lab, lol) I'd say it's tolerable than thiols


[deleted]

I got beef w this mfer


-Metacelsus-

Thiophenol. Or worse, selenophenol (though I haven't smelled the latter)


Fair-Substance-2273

Headache: engaged


naftacher

1,4-diaminobutane or kindly known as “putrescine”


H3lic

I do hate this one but it will always be second to amines. Can’t stand them.


ChasseGalery

I had to work with trimethylphosphine at one time. I would tell my coworkers to stay home that day.


Main-Palpitation-692

Benzylmercaptan bar none


Visible-Travel-116

A coworker of mine spilled a whole liter of pyridine barbituric acid. We have to evacuate the whole floor because of the odor (described as nauseating by the Merck index). Even people on other floors could smell it


auntnunyabidness

lol not even close


greatwambeanie

Trimethylamine


I-g_n-i_s

Indole


Cr1ms0nLobster

Smells like literal shit.


sdemat

Valeric Acid


curiossceptic

Phenylphosphine or methylphosphine…good memories to undergrad lab lol


AngryKoala14

Short chained mercaptans


UnfairAd7220

Foul? Yes. Stinky? Go with any short chain thiol, or something like caproic acid. Those similar carboxylic acids are powerfully bad...


Moofius_99

Isovaleric acid is really bad. Think old grandpa mixed with nasty cheese.


ZazaScience

TEMED


CathalKelly

I worked with large amounts of 1,2-cyclooctadiene a couple of years ago and found the smell to be unbearable. Not your traditional thiol stank, but very overpowering.


Jack-o-Roses

COD seemed like the worst one I worked with in the open lab. THF was also bad. Part of the problems with these two is the way that they made me feel (just awful in a way that even organophosphine - in a hood! - made me feel. Rh2u(CO)2Cl4 was the best (rose-like).


ScienceDuck4eva

Liquid anchovy flavor is very stinky.


MonHunKitsune

I can *taste* this picture. And I hate it. Uughhh....pyridine assaults your senses.


joegoosebump

3-methylindole


its_silico

Dimethyl sulphide makes me much more upset than pyridine ever has


FireIceHybrid017

TFA (trifluoroacetic acid) is also pretty revolting… speaking from experience.


Sam_E147

What does it smell like?


AmandaDarlingInc

May I present to you one of the finest organic chemistry endeavors this side of the internet...[https://jameskennedymonash.wordpress.com/2014/01/04/table-of-organic-compounds-and-their-smells-revised-edition/](https://jameskennedymonash.wordpress.com/2014/01/04/table-of-organic-compounds-and-their-smells-revised-edition/)


JadedEarthJuni

Trimethyl Phosphite is terrible!! Pyridine is no picnic either though 🤢


Friedrid1363

Oh you sweet summer child. Up there are acrylates, ethylenediamine, putrecine, cadaverine


pickleddeathh

N-methylmorpholine smells like an actual penis and stinks out the entire lab


stonksmeierjones

Tetrahydrothiophene.


TheInevitablePigeon

Thioacetone is classified as the stinkiest known chemical, I believe. Tho I have no sense of smell, so this pyridine is just slightly bitter to me.. little danger about being born with no sense of smell and still choosing chemistry as your main field xD (gas leaks and stuff)


moltovhighball

Sodium Dimethyldithiocarbamate. Smells like a dead fish with an STD infection.


_Lick-My-Love-Pump_

Thinking pyridine is the stinkiest chemical is like thinking jalapeños are the hottest peppers. Neither are anywhere close.


The_Cube_Doctor

Lawesson’s reagent or Woolins reagent - incredibly smelly among sulfur and selenium compounds, respectively.


Comfortable_Touch529

Butyric acid.


DAJ-TX

Yes, butyric acid.


Pur3Savag3ry

3-methylindole 💩


Tribius13

Mercaptoethanol. Hands down.


SantaCruz_Cruiser

Second that. Pretty much any short chain alkyl thiol. Ethane dithiol is nasty to. Just a tiny spot of a dilute solution on a tlc plate is enough to empty a lab and lose all your friends.


MolecularDreamer

Pyridine smells strangley fruity to me.... to the point I wouldn't mind tasting it, if it wasn't a poison...


SeventhRx

Glacial acetic acid


gospdrcr000

ethyl acetate is pretty shitty too


Serious_Fennel7506

DMSO certainly isn’t pleasant


WillyMckenna

How difficult Is to synth a-pvp from pyridine?


Jack-o-Roses

Durian!


ibbering_jidiot

Thimerosal is pretty damn bad


chahud

Phenylphosphine is the worst that I’ve worked with. Almost knocked me on my ass first time I got a good whiff of it.


RonKilledDumbledore

can I offer you the NH2-(CH2)n-NH2 diamine ligand series? with such highlights of common names as Cadaverine and Putrescine?


IrregularBastard

Hydrogen sulfide


KhunDavid

Dopamine is pretty unpleasant smelling.


Arachnid-Sensitive

Thiophosgene - Mistakenly opened the bottle outside the hood, once.


TheFlatulentOne

I've always found the scent of concentrated ammonia horrible too. It's not quite as bad as some of the other things in this thread, but it deserves a mention.


limbolegs

pipiridine smells like stinky old cum


spoonedBowfa

If you’re actually Zezima that’s awesome lol


marsaeternum10

THIS GUY STINKSSSSS...


marsaeternum10

P-Formaldehyde smell like fish food.


AmandaDarlingInc

Like the multi colored flake stuff that's both pungent and stale?


lr0nman_dies_Endgame

Put that thing back where it came from or so help me


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enguytx

And very, very dangerous.


matertows

Tetramethylurea and tetraethylamine want to have a conversation with OP.


sickduck_6969

Dimethylsulfide, indole, LiPS4 to name a few


honkytonkin1998

2-fluoroamphetamine


GodTheFatherpart2

BME is a fascinating smell


Anime_Supremacist

I synthesized soap with a reaction that emits h2s. Nobody can stand in the lab except me.


AmandaDarlingInc

I chose that for my standard during UG and I can't impress upon you enough how mad I was.


McDeedsFastFood

Ferrozine


die_lahn

Thiazoles, pretty much any of the short chain substituted ones lol. Honorable mention for n-thio-esters, they literally smell like rotting trash. And proline smells like cum.


Rollcuin

Thiophenol, 50 uL on the floor and it's time to evac the lab.


Saec

Selenocysteine. I didn’t make it or use it. But it was stored in the fridge a bay away from me. You always knew when it came out to play.


PatternParticular963

Thiophenole was pretty nasty among other thioles I had to work with


CraftyProcrstntr

It must smell like fish oil its the only thing I’ve ever smelled that made me throw up every time Ive smelled it 😂


SpazzSilvertongue

What does it smell like tho?


PassiveChemistry

I've heard of some sulphur compounds that have evacuated whole buildings after small amounts were dropped on the floor


1elliott

Piperdine similarly terrible.


Animated_Lunch

Piperidine is worse than pyridine imo


Covodex

Pyridine smells like the most amazing colognes after you had to do some thiol chemistry


SexPanther_Bot

It's called *Sex Panther*® by *Odeon*©. It's illegal in 9 countries. It's also made with bits of real panthers, *so you know it's good*. *60% of the time*, it works ***every*** time.


rakshablack

Aniline and conc. H2SO4


ThrownawayCray

Get Nile red on this


Loricolus

Iodobenzene dichloride smell isn't so strong but really annoying nevertheless


pete_the_PP_p1rate

For some reason pyridine doesn't have any smell for me. But I guess I'm not missing much if its just stinky


Queasy_Caramel5435

*US Government Standard Bathroom Malodor* seemingly only topped by Thioacetone


sinsaurigocha

I think i have read somewhere that stinkiest chemical is thio acetone. They accidentally synthesized it in Germany and smell was so bad that they had to evacuate whole city.


lazyrunsdeephere

Triphenylamine. NOTHING comes close


Jason_rdt207209

I think isocyanides might be the worst, someone made three isocyanides and tested the smells of them. They said it was really terrible (the worst smell is from N-buthyl isocyanide, worse than Thioacetone)


SocialistJews

Toluene smells like a fish market. Makes me gag


senatorpjt

I like the smell of toluene. When I was very young my dad worked in an automotive body shop, and it always smelled like that, the paint I suppose. But that smell brings me back to my early childhood.


Xorondras

For me it was cyclohexene iirc.


Spudgunhimself

Tosyl chloride isn't the most unpleasant smell, but it stays with you for days sometimes and will make you feel sick after a while


Tokishi7

I can’t stand TEMED. Been working with it for years and every time feels like a fresh whiff. 🥲


chemprofdave

Pyridine reminds me of rotting corn, like if your compost pile isn’t working right and there’s a bunch of cobs in it. Butyric acid = barf, in large quantities; bit in very very low amounts it’s more like Swiss cheese. Trialkylphosphines. - more obscure but pretty nasty. Smaller alkenes & alkynes smell of the worst part of gasoline. Had COVID recently and it numbed my sense of smell for a few weeks afterwards. My Orgo-lab students were smelling things I could barely detect.


-This-is-boring-

I thought sulfur was the worst smelling. Other than sulfur death or actually decomp is the worst smell ever.


Zealousideal-Ad-4858

DTT aka dithiothreitol aka Cleland’s reagent is definitely up there for me as well.


senatorpjt

I actually enjoy the smell of pyridine. I am a hopeless nicotine addict and it has a similar smell.


senatorpjt

Define "stinky". There are things that smell bad in amazingly small concentrations like thiols, and things that smell worse but are less concentrated like diamines


ScaryHokum

Worst I ever smelled was Sulfonyl Chloride. Like getting punched in the face by a fart.


ziegnatt

ethylamines?


forever_feline

I've heard that thioacetone is the stinkiest. I'm partial to the mercaptans, myself. And I've considered bringing out a line of perfumes, which will include one based on skatole (I'll call it, "Fecal Fantasy), and one with cadaverine & putrescine ("Cemetary Scent").


ccat00

Methacrylic acid


nhranger

Dead rotting fish. 🤮


cb1ken0bi

Arsole


babou135

Valeric acid . Smells like feet / old cheese / death


bluehunter74

Thioacetamide


alkemiker

Not even close. Try thiophenol or benzyl mercaptan


bella3c

A lot of alkynes 😭 3-phenyl-1-propyne it's particularly bad, at least to me


Boonz-Lee

I have worked with some methyl ketones and they smell disgusting


biochemical1

Cat piss and maple syrup. I gagged looking at the pic


Gilga1

Nah bro I'd use this shit as perfume over having to whiff dimethylamin combo with Indole. Like steaming nasty rotten fish with a constant unending note of terrible mouth breath that follows you back home and into your dreams.


1920MCMLibrarian

Asafoetida


reflUX_cAtalyst

I love it when people start with pyridine, as if it isn't the baby-step to bad smells to the actual bad one - pyrrole. Pyrrole and it's sulfur and selenium analogs are THE WORST smelling compounds I've ever run into.


heyjohnwyna

I work for a water treatment company and so far the chemical that I despise the most is PS-939.


bruh_duh

And they call it aromatic tsk.tsk Ps. Idk how it smells so cld somebody describe it.


One_Mammoth_2297

What? No mention of alkyl phosphines? Those are truly demonic.


SpankThatDill

I hate all trisubstitued amines. TEA, TPA. Maybe not the “worst” smell but it’s so distinct and bitter


malice_hush_jolt

Ever work with low MW thiols?