BILLBUILDS
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is nitromethane any good as a solvent
im buying some nitromethane and theres a larger quantity and i was wondering if it haas any use in the lab such as a solvent or something else?
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Metacelsus
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Yes; I've used it once before as a reaction solvent, when I was trying a bunch of different solvents for a particular reaction to find the one that
gave the best yield. (Chloroform ended up winning.) Nitromethane is relatively uncommon to use as a solvent, however.
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karlos³
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It is good as cosolvent for some FC-reactions, like 3-acylation of indole.
But besides this, it is rarely used as solvent.
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Kapitan
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I've used it as a solvent for metal complexes on several occasions. It's in an unusual place where it's very polar and aprotic, but also basically
non-coordinating.
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JJay
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I don't think much of it as a solvent, but I used to use it for cleaning glassware when I had two gallons of it that I obtained for free. It dissolves
some things that denatured alcohol won't touch. It's cleaner-burning than gasoline and burns hotter than alcohol.
[Edited on 3-3-2017 by JJay]
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Metacelsus
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Keep in mind that its pKa is 10.2, so I don't think it can be considered aprotic (if one defines protic as "containing a labile H+"). For
comparison, methanol's pKa is 15.5, so nitromethane is more than 100,000 times as acidic. Nitromethane won't act as a hydrogen bond donor, however.
To elaborate on the reaction I was talking about earlier in the thread: it involved a complicated rearrangement of a zwitterion formed by trapping of
a benzyne. The solvent had to be acidic enough to donate a proton to the carbanion, but most normal protic solvents (alcohols, amines, carboxylic
acids, etc.) would cause side reactions with the benzyne. Chloroform was best in the end.
[Edited on 3-3-2017 by Metacelsus]
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Chemetix
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Holy hell is it a good solvent!! It gels Nitrocellulose beautifully, and will solvate resins that other things won't touch. Nitroethane does a better
job for some resins and glues I found. I decanted some NM off one day while out in a remote area, and while in the process of adding a small amount of
aliphatic amine to the aliquot, I set the bottle of NM down on the bonnet of my car. A drop had run down the side and made a ring with the base in
contact with the bonnet. It was back to bare metal in half an hour.
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clearly_not_atara
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| Quote: | | i was wondering if it haas any use in the lab |
Nitromethane can be converted to hydroxylamine and carbon monoxide by concentrated sulfuric acid, for one. I think iron powder will reduce
nitromethane to formaldoxime.
It will also condense with paraformaldehyde to form nitroethanol and nitroethylene; nitroethylene is a useful dienophile and can be reduced to
variously nitroethane, acetaldoxime, or ethylamine by various methods, which are also useful. Acetaldoxime is easily converted to acetonitrile or
acetaldehyde.
Nitromethane can also be used as a solvent, but it's more interesting as an intermediate, IMO.
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Texium
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Thread Moved
3-3-2017 at 15:11 |
Melgar
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Nitromethane is the only thing I have that will dissolve super glue (cyanoacrylate). It will dissolve other acrylic polymers as well. It reacts with
too many things to make for a very good reaction solvent, but it's great if all you care about is getting something into solution.
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JJay
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Acetone will dissolve cyanoacrylate but not very effectively. Halogenated solvents like DCM will dissolve cyanoacrylate more easily than nitromethane.
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Db33
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I consider Nitromethane not as a great solvent but DEFINITELY a useful chem in any lab.
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Rhodanide
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Quote: Originally posted by BILLBUILDS  | | im buying some nitromethane and theres a larger quantity and i was wondering if it haas any use in the lab such as a solvent or something else?
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Can be made into some NASTY, NASTY stuff.
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Melgar
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Oh, nitromethane can be mixed with MEK and various other volatile organics to make a really hot-burning lamp fuel, that doesn't create soot. This can
be useful on occasion if you need an improvised heat source that burns hot, but you don't want to blacken your glass. The flame also looks pretty
cool. It's sort of greyish-white. Nitromethane mixed with a small amount of benzyl alcohol will burn with a really hot yellow-white flame, since the
nitromethane can produce enough oxygen to burn the soot that's formed while it's still hot enough to burn.
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Aqua-regia
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Good inert solution for nitrating solid organics For example naphtalene.
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