2,5-Dihydroxy-1,4-benzoquinone

changed changed 477211505 2,5-dihydroxy-1,4-benzoquinone.svg Skeletal formula of 2,5-dihydroxy-1,4-benzoquinone 2,5-dihydroxy-1,4-benzoquinone-3D-balls.png Ball-and-stick model of 2,5-dihydroxy-1,4-benzoquinone 2,5-Dihydroxycyclohexa-2,5-diene-1,4-dione 2,5-Dihydroxybenzoquinone 2,5-Dihydroxy-p-benzoquinone Anilic acid correct chemspider 62426 1/C6H4O4/c7-3-1-4(8)6(10)2-5(3)9/h1-2,7,10H QFSYADJLNBHAKO-UHFFFAOYAW O=C\1C(\O)=C/C(=O)C(/O)=C/1 correct chemspider 1S/C6H4O4/c7-3-1-4(8)6(10)2-5(3)9/h1-2,7,10H correct chemspider QFSYADJLNBHAKO-UHFFFAOYSA-N correct CAS 615-94-1 correct FDA 0KG5HVB52Z 69213 C1=C(C(=O)C=C(C1=O)O)O 6 4 4 yellow solidViault Guillaume Grée Danielle Das Saibal Yadav Jhillu Singh Grée René 2011 Synthesis of a Focused Chemical Library Based on Derivatives of Embelin, a Natural Product with Proapoptotic and Anticancer Properties https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201001627 European Journal of Organic Chemistry en 2011 7 1233–1241 10.1002/ejoc.201001627 1099-0690 subscription 210 to 212 pKa1 = 2.71Cotton F. Albert Murillo Carlos A. Villagrán Dino Yu Rongmin 2006-03-01 Uniquely Strong Electronic Communication between [Mo2] Units Linked by Dioxolene Dianions https://doi.org/10.1021/ja0582962 Journal of the American Chemical Society 128 10 3284 10.1021/ja0582962 0002-7863 subscription pKa2 = 5.18 PubChem 2,5-Dihydroxy-1,4-benzoquinone https://pubchem.ncbi.nlm.nih.gov/compound/69213 2026-01-27 pubchem.ncbi.nlm.nih.gov en 07 Warning H302 H312 H315 H319 H332 H335 P261 P264 P264+P265 P270 P271 P280 P301+P317 P302+P352 P304+P340 P305+P351+P338 P317 P319 P321 P330 P332+P317 P337+P317 P362+P364 P403+P233 P405 P501 Hydroxy-1,4-benzoquinone Tetrahydroxy-1,4-benzoquinone 2,5-Dihydroxy-1,4-benzoquinone or 2,5-dihydroxy-para-benzoquinone is an organic compound with chemical formula C 6 H 4 O 4, 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. 10.1039/B617881B The compound is a weak acid: one or both hydroxyls can lose a proton to yield the anions C 6 H 3 O 4 - (pKa1 = 2.71) and C 6 H 2 O 4 2- (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. 10.1016/S0010-8545(01)00369-1 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. References Category:1,4-Benzoquinones Category:Hydroxybenzoquinones Category:Hydroquinones