Stability of o-Phthalaldehyde (OPA)

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Henrik Thomsen - 27 Jan 2004 19:40 GMT

Hello

I'm currently working with o-Phthalaldehyde (CAS: 643-79-8) and I am
very interested in knowing the stability of this chemical. On the
bottle is says that this chemical is "Air, light, temperature and
moisture sensitive".
1) I would like to know what are the reactions of instability under
the influence of "Air, light, temperature and moisture sensitive"?
2) And secondly I would like to know what is a critical air
composition, temperature level and relative humidity?
3)Thirdly is there anyway to stabilize OPA in dry form outside or
inside a closed container?

Best regards Henrik Thomsen

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Paul J. Franklin(moderator - sci.chem.organic.synthesis)
http://organicworldwide.net/sci.chem.organic.synthesis
Georgia State University <chepjf@panther.gsu.edu>
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Uncle Al - 28 Jan 2004 20:35 GMT

> Hello
>
[quoted text clipped - 8 lines]
> 3)Thirdly is there anyway to stabilize OPA in dry form outside or
> inside a closed container?

1) Aldehydes free radical air oxidize to peracids. Keep them away
from oxygen, under argon.
2) Dials will reversibly hydrate and cyclize in the presence of
moisture (and a trace of acid), especially if there is electron
withdrawl at the carbonyl.
3) Warming things speeds up their reactions.
4) Conjugated aromatic systems are heir to photochemistry, as are
conjugated carbonyls. Decarbonlylation is a common reaction.

Given the cost of the stuff, keep it in its brown bottle under argon
in the refrigerator. Warm to ambient before opening under inert gas
blanket.

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Paul J. Franklin(moderator - sci.chem.organic.synthesis)
http://organicworldwide.net/sci.chem.organic.synthesis
Georgia State University <chepjf@panther.gsu.edu>
Atlanta, GA

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Natural Science Forum / Chemistry / Organic Synthesis / January 2004

Stability of o-Phthalaldehyde (OPA)