2,5-Dihydroxy-1,4-benzoquinone or 2,5-dihydroxy-para-benzoquinone is an organic compound with chemical formula , formally derived from 1,4-benzoquinone by replacing two hydrogen atoms with hydroxyl (OH) groups. It is one of seven dihydroxybenzoquinone isomers. It is a yellow solid with planar moleculesSemmingsen, Dag "The crystal and molecular structure of 2,5-dihydroxy-1,4-benzoquinone at −162 °C" Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry 1977, volume B31, 11-14. that exhibits ferroelectric properties.Horiuchi, Sachio; Kumai, Reiji; Tokura, Yoshinori "Hydrogen-bonded donor-acceptor compounds for organic ferroelectric materials" Chemical Communications 2007, 2321-2329.
The compound is a weak acid: one or both hydroxyls can lose a proton to yield the anions (pKa1 = 2.71) and (pKa2 = 5.18), respectively. The latter forms a variety of metal complexes, functioning as a binucleating ligand.Kitagawa, Susumu; Kawata, Satoshi "Coordination compounds of 1,4-dihydroxybenzoquinone and its homologues. Structures and properties" Coordination Chemistry Reviews 2002, volume 224, 11-34.
The compound has been identified as partly responsible for the color of aged cellulosic materials.Hosoya, Takashi; French, Alfred D.; Rosenau, Thomas "Chemistry of 2,5-dihydroxy-[1,4]-benzoquinone, a key chromophore in aged cellulosics" Mini-Reviews in Organic Chemistry 2013, volume 10, pp. 309-315.
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