Alchemica
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How good an ethylating agent is ethyl chloride?
Some adult shops locally (don't know what kinky use it has) have started to sell ethyl chloride spray. I'm curious if it is good enough to use instead
of EtBr or EtI in alkylations eg Williamson ether synthesis, enolate alkylations etc, at the cost of a slower reaction rate and low boiling
temperature? I've seen some Williamson ether syntheses can use catalytic iodide to enhance the reaction rate of less reactive haloalkanes - would that
be a good way to go?
Like would ethylating a phenol by dissolving the phenol, potassium carbonate and a bit of NaI in some acetone, then streaming through the ethyl
chloride give appreciable yields of the ether, or is it just too unreactive and volatile?
Many thanks in advance!
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clearly_not_atara
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| Quote: | | don't know what kinky use it has |
EtCl has been used for cryotherapy. It is sprayed onto the skin and evaporates rapidly, producing a strong cooling effect but not going below 12 C,
the bp. It obviously must be a weak enough ethylating agent on its own that it wasn't banned for causing cancer.
It's either being used to relieve pain or to cause it, though even though it won't freeze the skin it can still "burn" you if applied too
aggressively. I really hope nobody is inhaling it intentionally.
| Quote: | | I've seen some Williamson ether syntheses can use catalytic iodide to enhance the reaction rate of less reactive haloalkanes - would that be a good
way to go? |
Yes
| Quote: | | Like would ethylating a phenol by dissolving the phenol, potassium carbonate and a bit of NaI in some acetone, then streaming through the ethyl
chloride give appreciable yields of the ether, or is it just too unreactive and volatile? |
Before you try to design a reaction procedure, you need to be able to do things like looking up the boiling points and solubilities of your reagents.
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bnull
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Quote: Originally posted by clearly_not_atara  | | Quote: | | don't know what kinky use it has |
It's either being used to relieve pain or to cause it, though even though
it won't freeze the skin it can still "burn" you if applied too aggressively. I really hope nobody is inhaling it intentionally.
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They are inhaling it. EtCl, despite neurotoxicity from prolonged use, is used by some as a 'sexual enhancer', like amyl nitrite used to be (and still
is). We sometimes forget that humans are weird animals.
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jackchem2001
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Ethyl chloride with catalytic iodide seems like it would have a good chance of success. Here is a loosely relevant section from Clayden's that implies
ethyl chloride is reasonably reactive on its own: 
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Mateo_swe
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If ethyl chloride is sold and used in the same way "poppers" were used i would think they soon will remove it from the stores.
At least where i live they remove anything similar that starts to sell in the stores.
Its just a gap in time where the laws havent caught up with the recent developments.
So get it while you can as it probably wont be up for sale for long.
Politicians just love to decide what you can do and not, and banning is their favorite thing to do.
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