2,5-Dihydroxy-1,4-benzoquinone

2,5-Dihydroxy-1,4-benzoquinone
Skeletal formula of 2,5-dihydroxy-1,4-benzoquinone
Skeletal formula of 2,5-dihydroxy-1,4-benzoquinone
Ball-and-stick model of 2,5-dihydroxy-1,4-benzoquinone
Ball-and-stick model of 2,5-dihydroxy-1,4-benzoquinone
Names
Preferred IUPAC name
2,5-Dihydroxycyclohexa-2,5-diene-1,4-dione
Other names
  • 2,5-Dihydroxybenzoquinone
  • 2,5-Dihydroxy-p-benzoquinone
  • Anilic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.505 Edit this at Wikidata
UNII
  • InChI=1S/C6H4O4/c7-3-1-4(8)6(10)2-5(3)9/h1-2,7,10H checkY
    Key: QFSYADJLNBHAKO-UHFFFAOYSA-N checkY
  • InChI=1/C6H4O4/c7-3-1-4(8)6(10)2-5(3)9/h1-2,7,10H
    Key: QFSYADJLNBHAKO-UHFFFAOYAW
  • C1=C(C(=O)C=C(C1=O)O)O
  • O=C\1C(\O)=C/C(=O)C(/O)=C/1
Properties
C6H4O4
Molar mass 140.094 g·mol−1
Appearance yellow solid[1]
Melting point 210 to 212 °C (410 to 414 °F; 483 to 485 K)[1]
Acidity (pKa) pKa1 = 2.71[2]
pKa2 = 5.18[2]
Hazards
GHS labelling:[3]
GHS07: Exclamation mark
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
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

2,5-Dihydroxy-1,4-benzoquinone or 2,5-dihydroxy-para-benzoquinone is an organic compound with chemical formula C
6H
4O
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 molecules[4] that exhibits ferroelectric properties.[5]

The compound is a weak acid: one or both hydroxyls can lose a proton to yield the anions C
6H
3O−
4 (pKa1 = 2.71) and C
6H
2O2−
4 (pKa2 = 5.18), respectively.[2] The latter forms a variety of metal complexes, functioning as a binucleating ligand.[6]

The compound has been identified as partly responsible for the color of aged cellulosic materials.[7]

References

  1. ^ a b Viault, 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". European Journal of Organic Chemistry. 2011 (7): 1233–1241. doi:10.1002/ejoc.201001627. ISSN 1099-0690.
  2. ^ a b c Cotton, F. Albert; Murillo, Carlos A.; Villagrán, Dino; Yu, Rongmin (2006-03-01). "Uniquely Strong Electronic Communication between [Mo2] Units Linked by Dioxolene Dianions". Journal of the American Chemical Society. 128 (10): 3284. doi:10.1021/ja0582962. ISSN 0002-7863.
  3. ^ PubChem. "2,5-Dihydroxy-1,4-benzoquinone". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-01-27.
  4. ^ Semmingsen, 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.
  5. ^ Horiuchi, Sachio; Kumai, Reiji; Tokura, Yoshinori "Hydrogen-bonded donor-acceptor compounds for organic ferroelectric materials" Chemical Communications 2007, 2321-2329. doi:10.1039/B617881B
  6. ^ Kitagawa, Susumu; Kawata, Satoshi "Coordination compounds of 1,4-dihydroxybenzoquinone and its homologues. Structures and properties" Coordination Chemistry Reviews 2002, volume 224, 11-34. doi:10.1016/S0010-8545(01)00369-1
  7. ^ 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.


allikas: http://en.wikipedia.org/wiki/2,5-Dihydroxy-1,4-benzoquinone