Melgar
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Possible accidental synthesis of bromonitromethane?
I ran out of CH2Cl2 for extracting bromine, and so tried to use nitromethane instead, rather than throw away the rest of the bromine. It didn't react
in tiny amounts, or slightly larger amounts, so I went ahead with it. Got maybe 25 mL or so. Considering they're both acidic/acid-forming oxidizers,
it didn't seem especially dangerous. Well, I forgot about it for a few weeks, and the next time I went to open the cap, a cloud of HBr fumes escaped.
I quickly shut it. That wasn't expected. The solution was also less orange and more brown.
After thinking about it, my guess is bromonitromethane. It probably formed from trace amounts of water in the nitromethane, similar to how
chloroacetone forms. The HBr would keep things acidic, favoring monobromination. I did read a paper recently lauding the usefulness of
bromonitromethane, although it seems like it's mostly used for reactions with organic sulfur-containing compounds:
http://pubs.rsc.org/en/Content/ArticleLanding/1986/P1/P19860...
It can be reacted with tributylborane to give 1-nitropentane, and I'm sure there are plenty of similar reactions possible.
Of course, that's assuming that this is what I'll have when all the HBr escapes, and there's no guarantee of that. But as least initially, is there
any reason for ruling this out as the compound that formed?
The first step in the process of learning something is admitting that you don't know it already.
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Cryolite.
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If HBr was released, I would be more concerned with the potential formation of bromopicrin. Add some to a large excess of water and see if an oily
layer drops out.
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Melgar
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Quote: Originally posted by Cryolite.  | | If HBr was released, I would be more concerned with the potential formation of bromopicrin. Add some to a large excess of water and see if an oily
layer drops out. |
Bromopicrin would need basic conditions though, correct? It's similar to the haloform reaction, in that with basic conditions all three hydrogens
react, and with acidic conditions, only one does. And the HBr gas indications that conditions are rather acidic.
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