C8136 Aldrich

Chloranilic acid

Synonym: 2,5-Dichloro-3,6-dihydroxy-p-benzoquinone, 2,5-Dichloro-3,6-dihydroxy-2,5-cyclohexadiene-1,4-dione, NSC 6108, NSC 97383



Related Categories Building Blocks, C3 to C6, Carbonyl Compounds, Chemical Synthesis, Ketones,
mp   ≥300 °C(lit.)



25 g in glass bottle


Reactant involved in:
• Acting as a proton donor in reactions studying dimensionality control1
• Synthesis of dimethylbipyridyl complexes2
• Synthesis of (nonylbenzimidazolylmethyl)benzene for preparation of neutral altitudinal rotor-shaped dirhenium metallacycles3
• Charge-transfer reactions with metoprolol tartrate4
• Salt formation with organic bases5
• Synthesis of osmium metalla-rectangles with anticancer activity6

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≥98% (HPLC), powder

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Safety Information

GHS07  GHS07
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WGK Germany 


Certificate of Analysis

Certificate of Origin

Protocols & Articles
Peer-Reviewed Papers


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1. Dimensionality Control of Vapochromic Hydrogen-Bonded Proton-Transfer Assemblies Composed of a Bis(hydrazone)iron(II) Complex M. Chang, et al. Inorg. Chem. 50, 8308-8317, (2011)


2. 4,4'-, 5,5'-, and 6,6'-dimethyl-2,2'-bipyridyls: The structures, phase transitions, vibrations, and methyl group tunneling of their complexes with chloranilic acid G. Bator, et al. J. Chem. Phys. 135, 044509/1-044509/11, (2011)

3. Adaptation toward Restricted Conformational Dynamics: From the Series of Neutral Molecular Rotors P. Rajakannu, et al. Organometallics 30, 3168-3176, (2011)

4. Spectrophotometric determination of metoprolol tartrate based on the charge transfer reaction with chloranilic acid L. Yu, et al Huaxue Shiji 32, 1003-1005, (2010)

5. Salts and co-crystals of chloranilic acid with organic bases: is it possible to predict a salt formation? K. Molcanov and B. Kojic-Prodic CrystEngComm 12, 925-939, (2010)

6. Anticancer activity of osmium metalla-rectangles N. P. E. Barry, et al. Dalton Trans. 39, 2816-2820, (2010)


[Spectrophotometric and HPLC evaluation of ceftazidime stability]. Palade B, Cioroiu B, Lazăr D, et al. Rev. Med. Chir. Soc. Med. Nat. Iasi. 114(1), 260-5, (2010)


Oxidative double dehalogenation of tetrachlorocatechol by a bio-inspired CuII complex: formation of chloranilic acid. Bruijnincx PC, Viciano-Chumillas M, Lutz M, et al. Chemistry 14(18), 5567-76, (2008)


[Spectrophotometric determination of azithromycin by charge transfer reaction]. Huang W, Liu XJ, and Zhao FL Guang Pu Xue Yu Guang Pu Fen Xi 26(5), 913-6, (2006)


Application of pi-acceptors to the spectrophotometric determination of lisinopril in commercial dosage forms. Rahman N, Anwar N, and Kashif M Il Farmaco 60(6-7), 605-11, (2005)


Synthesis, structure, and magnetic properties of valence ambiguous dinuclear antiferromagnetically coupled cobalt and ferromagnetically coupled iron complexes containing the chloranilate(2-) and the significantly stronger coupling chloranilate(*3-) radical trianion. Min KS, DiPasquale AG, Golen JA, et al. J. Am. Chem. Soc. 129(8), 2360-8, (2007)


Spectroscopic characterization of charge-transfer complexes of morpholine with chloranilic and picric acids in organic media: crystal structure of bis(morpholinium 2,4,6-trinitrocyclohexanolate). Refat MS, El-Zayat LA, and Yeşilel OZ Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 75(2), 745-52, (2010)


Vanadium-induced nucleophilic IPSO substitutions in a coordinated tetrachlorosemiquinone ring: formation of the chloranilate anion as a bridging ligand. Chatterjee PB, Bhattacharya K, Kundu N, et al. Inorg. Chem. 48(3), 804-6, (2009)


Spin exchange effects on the physicochemical properties of tetraoxolene-bridged bimetallic complexes. Guo D and McCusker JK Inorg. Chem. 46(8), 3257-74, (2007)


Spectrophotometric determination of terfenadine in pharmaceutical preparations by charge-transfer reactions. Khaled E Talanta 75(5), 1167-74, (2008)


Exploiting pi-acceptors for the determination of thyroid hormones (T3 and T4) using a single interface flow system. Silvestre CI, Santos JL, Lima JL, et al. Talanta 79(4), 1177-80, (2009)


Spectroscopic and structural characterization of the charge-transfer interaction of N,N'-bis-alkyl derivatives of 1,4,6,8-naphthalenediimide with chloranilic and picric acids. Refat MS, Ahmed HA, Grabchev I, et al. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 70(4), 907-15, (2008)


Preparation and spectroscopic studies on charge-transfer complexes of 2,2'-bipyridine with picric and chloranilic acids. Teleb SM and Gaballa AS Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 62(1-3), 140-5, (2005)


Utility of certain sigma- and pi-acceptors for the spectrophotometric determination of ganciclovir in pharmaceutical formulations. Gouda AA Talanta 80(1), 151-7, (2009)


A partial proton transfer in hydrogen bond O-H···O in crystals of anhydrous potassium and rubidium complex chloranilates. Biliškov N, Kojić-Prodić B, Mali G, et al. J. Phys. Chem. A 115(14), 3154-66, (2011)


Hydrogen bonding in two solid phases of phenazine-chloranilic acid (1/1) determined at 170 and 93 K. Gotoh K, Asaji T, and Ishida H Acta Crystallogr. C 63(Pt 1), o17-20, (2007)


Temperature dependence of one-dimensional hydrogen bonding in morpholinium hydrogen chloranilate studied by 35Cl nuclear quadrupole resonance and multi-temperature X-ray diffraction. Tobu Y, Ikeda R, Nihei TA, et al. Phys. Chem. Chem. Phys. 14(35), 12347-54, (2012)


Spectrophotometric analysis of selective serotonin reuptake inhibitors based on formation of charge-transfer complexes with tetracyanoquinodimethane and chloranilic acid. Darwish IA and Refaat IH J. AOAC Int. 89(2), 326-33, (2006)


Spectrophotometric, Fourier transform infrared spectroscopic and theoretical studies of the charge-transfer complexes between methyldopa [(S)-2 amino-3-(3,4-dihydroxyphenyl)-2-methyl propanoic acid] and the acceptors (chloranilic acid, o-chloranil and dichlorodicyanobenzoquinone) in acetonitrile and their thermodynamic properties. Sharma K, Sharma SP, and Lahiri SC Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 92, 212-24, (2012)


Reductions by aquatitanium(II). Yang Z and Gould ES Dalton Trans. (10), 1781-4, (2005)


Intermolecular hydrogen bond complexes by in situ charge transfer complexation of o-tolidine with picric and chloranilic acids. Refat MS, Saad HA, and Adam AM Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 79(3), 672-9, (2011)


Spectrophotometric determination of nizatidine and ranitidine through charge transfer complex formation. Walash M, Sharaf-El Din M, Metwalli ME, et al. Arch. Pharm. Res. 27(7), 720-6, (2004)


Indirect flow-injection spectrophotometric determination of meloxicam, tenoxicam and piroxicam in pharmaceutical formulations. Al-Momani IF Anal. Sci. 22(12), 1611-4, (2006)


Spectrophotometric, FTIR and theoretical studies of the charge-transfer complexes between isoniazid (pyridine-4-carboxylic acid hydrazide) and the acceptors (p-chloranil, chloranilic acid and tetracyanoethylene) in acetonitrile, their association constants, thermodynamic properties and other related properties. Bagchi Chattaraj S, Sharma K, Chakrabortty A, et al. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 95, 637-47, (2012)


Molecular characterization of chloranilic acid degradation in Pseudomonas putida TQ07. Treviño-Quintanilla LG, Freyre-González JA, Guillén-Garcés RA, et al. J. Microbiol. 49(6), 974-80, (2011)


[Fluorescence spectroscopy determination of lomefloxacin by charge transfer complex formation with chloranilic acid]. Du LM, Zhou J, and Yuan JM Guang Pu Xue Yu Guang Pu Fen Xi 24(12), 1623-5, (2004)


Merck 14,2079

Beil. 8,IV,2707

FT-IR 2 (1), 716:D / FT-IR 1 (1), 455:B / IR-Spectra (2), 240:G / IR-Spectra (3), 269:E / RegBook 1 (1), 493:L / Sigma FT-IR 1 (2), 369:A / Structure Index 1, 71:E:2

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