According to IUPAC and US-EPA, no acid/basic dissociation (Does not demonstrate a dissociation constant between pKa2 and pKa10).
IUPAC http://sitem.herts.ac.uk/aeru/iupac/Reports/368.htm
EPA https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-043301_01-Sep-06.pdf
Thanks so much, dear Valerio Paolini I found the references very useful. Cheers
Dear Ali Behrad Vakylabad thank you for posting this interesting technical question on RG. As already mentioned in previous answers, furfural is a heterocyclic aldehyde, and as such it is a neutral molecule. Under "normal" conditions, it would be considered neither acidic nor basic. However, as mentioned by Pedro Nakasu
it would be helpful if you would indicate what type of acidity you have in mind. In terms of the Lewis acid-base definition, furfural is clearly a Lewis base as it has several non-bonding electron pairs at the two oxygen atoms. Most likely, Lewis acids such as BF3, AlCl3, or transition metal cations will coordinate to the ring-oxygen atom. However, I never came across any transition metal complexes containing coordinated furfural.Good luck with your work and please stay safe and healthy! With best wishes, Frank Edelmann
Indeed, furfural is a neutral molecule in general terms. At the same time, it can be protonated (being a Lewis base as mentioned earlier), as well as deprotonated under specific conditions.
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