Chloranilic acid

Chloranilic acid^[1]
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	87-88-7;
3D model (JSmol)	Interactive image;
ChemSpider	59971;
ECHA InfoCard	100.001.619
EC Number	201-780-7;
PubChem CID	66604;
UNII	YJ8L3BB7Y4;
CompTox Dashboard (EPA)	DTXSID3058959 ;
	InChI InChI=1/C6H2Cl2O4/c7-1-3(9)5(11)2(8)6(12)4(1)10/h9,12H Key: IPPWILKGXFOXHO-UHFFFAOYAU;
	SMILES Cl\C1=C(/O)C(=O)C(\Cl)=C(\O)C1=O;
Properties
Chemical formula	C6H2Cl2O4
Molar mass	208.98 g/mol
Appearance	orange or red crystals or powder
Density	1.96 g/cm3
Melting point	≥300 °C
Acidity (pKa)	2.95, 4.97
Hazards
	GHS labelling:
Pictograms
Signal word	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

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]

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.

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[1] "Chloranilic acid". Sigma-Aldrich.

[Andersen-2] 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.

[cmpx-3] 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.

[1]

[2]

[3]

Chloranilic acid

See also

References