Chloranil

Chemical Properties

YELLOW-GREEN POWDER

Uses

antipsoriatic

Uses

p-Chloranil is used as a dye intermediate, oxidizing agent, vulcanizing agent and dehydrogenation reagent. It is also used to make chloranil electrodes for pH measurements. Further, it serves as a hydrogen acceptor and used for the aromatization reactions such as conversion of cyclohexadienes to the benzene derivatives. It is used to test the secondary amine. In addition to this, it is employed as a precursor to prepare diaziquone, which is used as a cancer chemotherapeutic agent.

Uses

Tetrachloro-1,4-benzoquinone is a potential intermediate in the process of pentachlorophenol-induced carcinogenicity.

Uses

Agricultural fungicide, dye intermediate, reagent. manufacture of electrodes for pH measurement.

Definition

ChEBI: A member of the class of 1,4-benzoquiones that is 1,4-benzoquinone in which all four hydrogens are substituted by chlorines.

Synthesis Reference(s)

Tetrahedron, 34, p. 1577, 1978 DOI: 10.1016/0040-4020(78)80185-9

General Description

Yellow powder with a slight odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Chloranil is sensitive to excessive light and heat. Chloranil is incompatible with strong oxidizing agents. Chloranil reacts with alkalis.

Hazard

Skin irritant.

Fire Hazard

Flash point data for Chloranil are not available; however, Chloranil is probably combustible.

Purification Methods

Crystallise p-chloranil from acetic acid, acetone, *benzene, EtOH or toluene, dry it in a vacuum over P2O5, or from acetic acid and drying over NaOH in a vacuum desiccator. It can be sublimed under vacuum at 290o. A sample may contain significant amounts of the o-chloranil isomer as impurity. Purify it by triple sublimation under vacuum and recrystallise before use. It is a skin and mucous membrane irritant. [UV: Pummerer et al. Chem Ber 85 545 1952, Brook J Chem Soc 5040 1952, Beilstein 7 IV 2083.]