Sciencemadness Discussion Board

Can amateurs buy thionyl chloride from www.chemsavers.com?

Cou - 12-1-2020 at 12:22

chemsavers sells many benign chemicals to amateurs thru their amazon and ebay accounts, but i dont know much about their main website.

if they refuse, will i get a refund?

hesitant to ask them, because it's better to ask for forgiveness than for permission.

[Edited on 12-1-2020 by Cou]

Chemsavers.com

MadHatter - 12-1-2020 at 14:57

I've ordered from these people in the past.
They're out of Virginia. I've never had a problem
with them and unless there have been changes
to policy that I'm unaware of you shouldn't have
a problem. They seem to prefer PayPal. I don't
know anything about thionyl chloride but the
prices currently on their site range from $24.30
per 100ml to $193.50 per 4 litres(99%).

Personally, I don't think you'll have problem.


[Edited on 2020/1/12 by MadHatter]

monolithic - 12-1-2020 at 15:58

I believe if it's anything questionable, which probably includes SOCl3, you have to fill out an intended use form. I only order solvents from them so I've never had to do this.

Thionyl Chloride SOCl2

MadHatter - 12-1-2020 at 18:20

monolithic, you may be correct on this one. This
particular compound is nasty, where on combination
with H2O produces SO2 and 2HCl. I don't even want
to imagine the effect on the lungs. It's listed as a
CLASS 3 material in the Chemical Weapons
Convention meaning that it can be used alone or in
production of other chemical weapons. I'll steer
clear of this one.

Cou - 12-1-2020 at 18:41

ok, i was hoping to use SOCl2 to make acid chlorides from carboxylic acids, so i can make esters of phenol and tertiary alcohols.

AvBaeyer - 12-1-2020 at 20:33

I advise you to avoid using thionyl chloride in a home lab setting. This is truly nasty stuff and almost always needs to be distilled before use. The reagent is generally used in excess when making acid chlorides and therefore distillation by some means is required to remove the excess. Also, copious amounts of SO2 and HCl are formed during the halogenation reaction which must be accounted for.

Phenolic and tertiary alcohol esters can be made using carbonyldiimidazole (CDI) as the activating reagent and dimethylaminopyridine (DMAP) as a catalyst. The only by-products are CO2 and imidazole. CDI is often available on Ebay or Amazon from ChemSavers. (It is actually an extremely versatile reagent for synthesis.) DMAP is available from ChemSavers - it's a catalyst so you do not need much.

If you have access to a good Chem Library see: H.A. Staub et.al, "Azolides in Organic Synthesis and Biochemistry" published by Wiley-VCH. It contains a few procedures and ample references.

Please, no thionyl chloride.

AvB

G-Coupled - 12-1-2020 at 22:20

How toxic is DMAP? Some people seem to insist that it's highly toxic, but its LD50 numbers don't seem to be too bad.

DavidJR - 13-1-2020 at 00:23

I don't think thionyl chloride is unmanageable in the home lab. Good ventilation is essential though.

draculic acid69 - 13-1-2020 at 01:29

Could socl2 be used to make phenol into chlorobenzene?

woelen - 13-1-2020 at 05:46

I have some SOCl2 and it indeed is not unmanageable. Storage is not easy though. You need a glass bottle with a very good cap (e.g. Schott Duran bottles with the red caps) and even then, over time you see degradation of the cap. SOCl2 reacts with moisture in air to form SO2 and HCl and especially the latter is nasty for metal objects, stored nearby. If you have a bottle of SOCl2, which is not perfectly sealed, then you'll get rusting of metal objects and degradation of paper objects nearby (e.g. labels on other nearby bottles).
SOCl2 has a very pungent smell (like sulfur dioxide, but with a strong pungency added to it, due to the HCl).

The direct corrosiveness and reactivity of SOCl2 make it a chemical which must be treated with respect, but on the other hand, its systemic toxicity is very low. HCl and SO2 both quickly degrade in the environment to harmless chloride and sulfate (by oxidation and neutralization of acid) and from an environmental point of view, SOCl2 is not more toxic than dilute HCl and sodium sufite.

With SOCl2 you can make really nasty chemicals though, by replacing hydroxyl groups by chlorine atoms. E.g. the benign triethanolamine (which is used in cosmetics as an hydrating agent) can be converted to an extremely nasty mustard agent (an exceptionally strong blistering agent, which easily kills you). Many more benign chemicals can be converted to extremely dangerous blistering or nerve agents. If you experiment with SOCl2 then you must know what you are chlorinating. The same is true for experimenting with PCl3, PCl5, POCl3 and to a lesser extent with SO2Cl2, SO2Cl(OH), CH3COCl and CH3CH2COCl. All these acyl chlorices and acidic chlorides can produce very nasty compounds in reactions with certain organics.

DavidJR - 13-1-2020 at 06:23

Quote: Originally posted by draculic acid69  
Could socl2 be used to make phenol into chlorobenzene?


Probably yes - but I personally wouldn't waste SOCl2 on that because it is less wastefully made from benzene directly. Also, I was able to buy chlorobenzene quite cheaply.

FYI if you're thinking of using chlorobenzene to make PhMgCl or PhLi, don't bother - it doesn't work very well at all. Stick to PhBr or PhI

karlos³ - 13-1-2020 at 08:00

"I have some SOCl2 and it indeed is not unmanageable. Storage is not easy though."

I agree much, it needs proper precautions and a good storage vessel.
My last SOCl2 ate through the cap over the course of five years in storage(there wasn't much in there after my last use anyways, maybe 5ml from formerly 100ml), but I guess that much volume over the liquid level contributed to the gasses being able to corrode the (plastic) cap.

Cou - 28-1-2020 at 20:50

Quote: Originally posted by AvBaeyer  
I advise you to avoid using thionyl chloride in a home lab setting. This is truly nasty stuff and almost always needs to be distilled before use. The reagent is generally used in excess when making acid chlorides and therefore distillation by some means is required to remove the excess. Also, copious amounts of SO2 and HCl are formed during the halogenation reaction which must be accounted for.

Phenolic and tertiary alcohol esters can be made using carbonyldiimidazole (CDI) as the activating reagent and dimethylaminopyridine (DMAP) as a catalyst. The only by-products are CO2 and imidazole. CDI is often available on Ebay or Amazon from ChemSavers. (It is actually an extremely versatile reagent for synthesis.) DMAP is available from ChemSavers - it's a catalyst so you do not need much.

If you have access to a good Chem Library see: H.A. Staub et.al, "Azolides in Organic Synthesis and Biochemistry" published by Wiley-VCH. It contains a few procedures and ample references.

Please, no thionyl chloride.

AvB


Wow thx man, just got that book thru interlibrary loan x) how do u guys even find this stuff? I dont know how to do literature search. SciFinder reaction search?

Chemi Pharma - 29-1-2020 at 03:56

I can sell pure Thionyl Chloride to you. 100ml for U$40 FOB price (without shipping cost). If you're interested call me at U2U.

Chemi Pharma - 29-1-2020 at 04:07

Quote: Originally posted by Cou  
Quote: Originally posted by AvBaeyer  
I advise you to avoid using thionyl chloride in a home lab setting. This is truly nasty stuff and almost always needs to be distilled before use. The reagent is generally used in excess when making acid chlorides and therefore distillation by some means is required to remove the excess. Also, copious amounts of SO2 and HCl are formed during the halogenation reaction which must be accounted for.

Phenolic and tertiary alcohol esters can be made using carbonyldiimidazole (CDI) as the activating reagent and dimethylaminopyridine (DMAP) as a catalyst. The only by-products are CO2 and imidazole. CDI is often available on Ebay or Amazon from ChemSavers. (It is actually an extremely versatile reagent for synthesis.) DMAP is available from ChemSavers - it's a catalyst so you do not need much.

If you have access to a good Chem Library see: H.A. Staub et.al, "Azolides in Organic Synthesis and Biochemistry" published by Wiley-VCH. It contains a few procedures and ample references.

Please, no thionyl chloride.

AvB


Wow thx man, just got that book thru interlibrary loan x) how do u guys even find this stuff? I dont know how to do literature search. SciFinder reaction search?


At really you can make acid chlorides in a easier way using TCCA and triphenyl phosphine or cyanuric chloride and TEA couple. See the attachments below:

I sell TCCA, Triphenyl Phosphine, Cyanuric Chloride and Triethylamine too at lower prices. Your major cost will be the international postal shipping price.

Cal me at U2U if you want.

Attachment: Acid chlorides from acids with Cyanuric Chloride and TEA.pdf (86kB)
This file has been downloaded 339 times

Attachment: acid chlorides with TCCA and triphenylphosphine.PDF (172kB)
This file has been downloaded 304 times

Cou - 29-1-2020 at 11:43

Quote: Originally posted by AvBaeyer  
I advise you to avoid using thionyl chloride in a home lab setting. This is truly nasty stuff and almost always needs to be distilled before use. The reagent is generally used in excess when making acid chlorides and therefore distillation by some means is required to remove the excess. Also, copious amounts of SO2 and HCl are formed during the halogenation reaction which must be accounted for.

Phenolic and tertiary alcohol esters can be made using carbonyldiimidazole (CDI) as the activating reagent and dimethylaminopyridine (DMAP) as a catalyst. The only by-products are CO2 and imidazole. CDI is often available on Ebay or Amazon from ChemSavers. (It is actually an extremely versatile reagent for synthesis.) DMAP is available from ChemSavers - it's a catalyst so you do not need much.

If you have access to a good Chem Library see: H.A. Staub et.al, "Azolides in Organic Synthesis and Biochemistry" published by Wiley-VCH. It contains a few procedures and ample references.

Please, no thionyl chloride.

AvB


that seems similar to the steglich esterificatoin. https://www.organic-chemistry.org/abstracts/literature/931.s...

draculic acid69 - 29-1-2020 at 16:49

Quote: Originally posted by DavidJR  
Quote: Originally posted by draculic acid69  
Could socl2 be used to make phenol into chlorobenzene?


Probably yes - but I personally wouldn't waste SOCl2 on that because it is less wastefully made from benzene directly. Also, I was able to buy chlorobenzene quite cheaply.

FYI if you're thinking of using chlorobenzene to make PhMgCl or PhLi, don't bother - it doesn't work very well at all. Stick to PhBr or PhI


Wasn't going to.i was just wondering if the OH on phenol behaves the same as a regular OH bcoz turning a phenol into a benzene takes extreme measures compared to a regular OH.in saying that would nabr+ h2so4+ phenol equal bromobenzene
Or would it take an extreme halogenating agent like thionyl bromide or pbr3.

AvBaeyer - 29-1-2020 at 20:15

There ain't no way any halogenating agent like SOX2, PX3, PX5 and similar (where X is your favorite halogen) will convert a phenol to a halide. Perhaps there is some exotic catalyst for the conversion but there is no possibility of a direct conversion. Please, consult a good org chem book to learn why.

Note to Cou: Glad you found the book. There is a lot of very interesting chemistry in there much of which can be done in a hobby lab setting. One of the most important things you will need to learn is how to do a thorough lit search for a question that you have. Takes time and lots of practice.

AvB

draculic acid69 - 1-2-2020 at 04:53

Quote: Originally posted by AvBaeyer  
There ain't no way any halogenating agent like SOX2, PX3, PX5 and similar (where X is your favorite halogen) will convert a phenol to a halide. Perhaps there is some exotic catalyst for the conversion but there is no possibility of a direct conversion. Please, consult a good org chem book to learn why


I didn't think so.just making sure.

Chemi Pharma - 9-2-2020 at 06:08

Quote: Originally posted by draculic acid69  
Quote: Originally posted by AvBaeyer  
There ain't no way any halogenating agent like SOX2, PX3, PX5 and similar (where X is your favorite halogen) will convert a phenol to a halide. Perhaps there is some exotic catalyst for the conversion but there is no possibility of a direct conversion. Please, consult a good org chem book to learn why


I didn't think so.just making sure.


At really there's an old research from Syracuse University, N.Y, USA, that claims for halogenation of alcohols and phenols too, with organic tertiary phosphine dihalides with a formula like R3PX2, where R= aryl or alkyl and X = Cl, Br or I. In the study they used triphenyl phosphine dibromide, obtained from triphenyl phosphine and bromine reaction in DMF or Acetonitrile media at 200ºC, converting phenol into phenyl bromide with 92% yield and p-cloro phenol into para-cloro,bromo benzene with 90% yield.

Take a look at the paper attached.

Attachment: Phenols-to-Halides-with triphenylPhosphine-Dihalide.PDF (284kB)
This file has been downloaded 301 times