=SkyNET=
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Azidoacetic acid and azidoacetone
Could they be made from chloroacetone and chloroacetic acid with an azide?
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The_Davster
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I can't see why not, but with theazidoacetic acid it would have to be made from the sodium chloroacetate and azide, otherwise you would just end up
with HN3. I doubt the stability of azidoacetic acid, afterall, nitroacetic acid instantly decomposes to nitromethane.
[Edited on 3-6-2006 by rogue chemist]
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=SkyNET=
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I did some reading and it seems stable although it might just be in situ.
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Formatik
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| Quote: | Originally posted by =SkyNET=
Could they be made from chloroacetone and chloroacetic acid with an azide? |
For azidoacetone, Forster and Fierz in Journal of the Chem. Soc., 93, 81 mix chloroacetone with conc. aq. NaN3 soln. in the presence of a little GAA. Azidoacetone, aka triazoacetone,
acetonylazoimide (CH3.CO.CH2.N3), is a colorless, refractive oil. Bp 2: 54 deg. D.: 18/18: 1.123. It is barely soluble in water, decomposes in storage
(JACS 1951, 73, 209 says a small sample has exploded after 6 months in storage in a dark area), it detonates on heating. Conc. H2SO4 splits off N2.
Warming it with aqueous alkalis decomposes it forming N2, NH3, and HN3 (Beilstein, Sys. No. 85., 661). For azidoacetic acid: preparation references
from ethyl ester of azidoacetic acid and aqueous KOH solution are in PATR A27. Some properties are also mentioned in Brethericks, according to which
it is neither explosively unstable or shock sensitive at even heated temperatures as long as impurities like iron or iron salts are not present.
[Edited on 6-10-2008 by Formatik]
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