Renaissance Man
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p-toluenesulonyl chloride advice
I was able to find what looks like a good sources for sulfonyl chlorides on ebay. They stock mainly garden variety lab chemicals, a good sign for
legitimacy. The toluene and benzene derivatives are priced at 37 and 57 USD respectively. I have a few questions about what I should do, I have looked
all around but I haven't been able to find much, and some of the questions require a more human input.
Should I be worried about having a squad of swat guys kicking in my door? The benzene derivative does not appear to be watched. I am just not sure how
much TsCl is, it might just be something that got grandfathered in.
Are there any behavioral differences between the two?
What do you think some good bases to work with might be? I can't really get a hold of any pyridine.
Could a reaction be done in such a way not to damage an amine moeity? this reaction is used to form a protecting group for the amine in other
reactions, but If possible I would not like it to eat up all of my reagent only to have to reduce the amine again. (could the sulfonamine be reduced
by acid catalyzed hydrolysis to form a salt?)
The benzene derivative is ~ 110% the efficiency of its bulkier toluene, but the former's price is 150% of the latter. I would go with Benzene sulfonyl
chloride if it would raise fewer eyebrows and is just as effective chemically; But if neither one would be a concern to the authorities or if they
were both just as bad why not save the $20 and go with what is more commonly used in the literature?
Sorry for assaulting you with all these questions. I just haven't been able to dig up enough information on this stuff.
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Paddywhacker
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Stick to the one that is used. That way if it doesn't work then you won't be left wondering if your substitution was at fault or not.
As for bases, the same source, unless I miss my guess, sells triethylene diamine (DABCO) in 500g lots at a very reasonable price.
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Renaissance Man
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Quote: Originally posted by Paddywhacker  | Stick to the one that is used. That way if it doesn't work then you won't be left wondering if your substitution was at fault or not.
As for bases, the same source, unless I miss my guess, sells triethylene diamine (DABCO) in 500g lots at a very reasonable price.
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Thanks, I completely passed over the DABCO. I can't believe I missed that.
Well they are both used, they are just a methyl group apart I would expect that they would behave almost identically, my real issue is if that holds
true then where do I choose the trade off between economics or anonymity.
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Nicodem
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Thread Moved
29-11-2010 at 09:48 |
Nicodem
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| Quote: Originally posted by Renaissance Man | | Should I be worried about having a squad of swat guys kicking in my door? The benzene derivative does not appear to be watched. I am just not sure how
much TsCl is, it might just be something that got grandfathered in. |
Benzene- and toluenesulfonyl chlorides being watched? I don't know anything about the legislation of your country, also because you never told what
country it is, but I find it odd that such trivial chemicals would be "watched" and unimaginable why they would be.
| Quote: | | Are there any behavioral differences between the two? |
Of course. They have different physical and spectroscopic properties. Though their chemical properties only differ in reaction kinetics if used as
electrophiles. But if used as substrates for electrophilic or radical reactions, then their chemistry is very different.
| Quote: | | What do you think some good bases to work with might be? I can't really get a hold of any pyridine. |
Impossible to properly answer as you forgot to describe what reaction they will be used for. Besides, if used as reagents they give different
products, so obviously they can not be substituted for each other if what you are after is a specific reaction product.
| Quote: | | Could a reaction be done in such a way not to damage an amine moeity? this reaction is used to form a protecting group for the amine in other
reactions, but If possible I would not like it to eat up all of my reagent only to have to reduce the amine again. (could the sulfonamine be reduced
by acid catalyzed hydrolysis to form a salt?) |
Both reagents react with free primary and secondary amines or anilines. Sulfonamides or aliphatic amines can not be easily hydrolysed, if at all. The
N-deprotection requires reductive cleavage. On the other hand, sulfanilides can be hydrolysed, at least as far as I remember.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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Renaissance Man
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I had read that Tosyl chloride was useful for converting alcohols to a alkyl chlorides through a tosylate intermediate that is cleaved. I know that
the p-toluene sulfonic acid is on the list (I must have recalled incorrectly that the acid halide was) but I would think that being so similar, and
probably much more useful than the acid that it would be looked as well. And I don't think that they have it on there to stop bootleggers of
penicillin. 
But as far as using them as reagents I was under the impression that they would behave fairly similarly, I mean the difference between a reaction
intermediate with a phenyl vs methylphenyl group is pretty small especially if you are going to cleave it off immediately, or at least that was my
thought. Of course there could be some funky steric hindrance or problems with ortho directing side reactions, but I would not expect it
I am in the US, who else would have such preposterous laws?
I was also vaguely considering buying some hydrazine hydrochloride but I think that would raise far more red flags than Tosyl chloride.
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497
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A possible alternative route to sulfonyl chlorides from OTC materials could go as follows:
Chloramine-T to toluenesulfonamide by reaction with sulfites, etc.
Then microwave acid hydrolysis of toluenesulfonamide to toluenesulfonic acid in dil. H2SO4. Ref
Then chlorination of toluenesulfonic acid with TCCA. I didn't know this was even possible until now. Ref
Looks reasonably easy and very OTC. At least easier than the diazotization route mentioned above..
If someone has access to the full references and can post them I would appreciate it..
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smuv
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That's TCT (sym-trichlorotriazine) not TCCA (trichloro-isocyanuric acid).
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497
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Shit. No wonder i was surprised.
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smuv
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lol. You don't know how many people have made this mistake.
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