Chloranilic acid
![]() | |
![]() | |
![]() | |
Names | |
---|---|
Preferred IUPAC name 2,5-Dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione | |
Other names 2,5-Dichloro-3,6-dihydroxy-1,4-benzoquinone 2,5-Dichloro-3,6-dihydroxybenzoquinone | |
Identifiers | |
CAS Number |
|
3D model (JSmol) |
|
ChemSpider |
|
ECHA InfoCard | 100.001.619 ![]() |
EC Number |
|
PubChem CID |
|
UNII |
|
CompTox Dashboard (EPA) |
|
InChI
| |
| |
Properties | |
Chemical formula | C6H2Cl2O4 |
Molar mass | 208.98 g/mol |
Appearance | orange or red crystals or powder |
Density | 1.96 g/cm3[2] |
Melting point | ≥300 °C |
Acidity (pKa) | 2.95, 4.97[3] |
Hazards | |
GHS labelling: | |
Pictograms | ![]() |
Warning | |
Hazard statements | H315, H319, H335 |
Precautionary statements | P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 |
Flash point | 135.4 °C (275.7 °F; 408.5 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
Chemical compound
Chloranilic acid is an organic compound with the chemical formula C6Cl2O2(OH)2. It is a red-orange solid. The compound is obtained by hydrolysis of chloranil:
- C6Cl4O2 + 2 H2O → C6Cl2O2(OH)2 + 2 HCl
It is centrosymmetric, planar molecule. It also crystallizes as a dihydrate.[2]
Chloranilic acid is a noteworthy hydroxyquinone that is somewhat acidic owing to the presence of the two chloride substituents. The conjugate base, C6H2Cl2O4]2- readily forms coordination complexes often linking pairs of many metal ions.[3]
See also
References
- ^ "Chloranilic acid". Sigma-Aldrich.
- ^ a b Andersen, E. K. (1967). "The Crystal and Molecular Structure of Hydroxyquinones and Salts of Hydroxyquinones. I. Chloranilic Acid". Acta Crystallographica. 22 (2): 188–191. doi:10.1107/S0365110X67000325.
- ^ a b Mostafa, S. I. (1999). "Complexes of 2,5-Dihydroxy-1,4-Benzoquinone and Chloranilic Acid with Second and Third Row Transition Elements". Transition Metal Chemistry. 24 (3): 306–310. doi:10.1023/A:1006944124791. S2CID 91429728.
- v
- t
- e