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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Soluble in ether and acetone. Slightly soluble in chloroform, dimethylformamide, solvent naphtha, benzene, carbon disulfide and carbon tetrachloride. Insoluble in water, cold petroleum ether, methanol, dibutyl phthalate and cold alcohol.
Notes
Incompatible with strong oxidizing agents and strong bases.
RUO – Research Use Only
General References:
- High potential quinones dehydrogenate many hydroaromatic systems by hydride abstraction.
- Reviews: Adv. Org. Chem., 2, 329 (1960); Chem. Rev., 67, 153 (1967); 78, 317 (1978).
- Forms complexes with many non-aromatic electron-donors, e.g. carbonyl compounds, esters, amides, lactones, lactams and alkyl iodides: J. Org. Chem., 53, 2163 (1988).
- Liu, B.; Li, X.; Stępień, M.; Chmielewski, P. J. Towards Norcorrin: Hydrogenation Chemistry and the Heterodimerization of Nickel(II) Norcorrole. Chem. Eur. J. 2015, 21 (21), 7790-7797.
- Paddy, V.; van Tonder, J. J.; Steenkamp, V. In vitro Antioxidant Activity and Polyphenolic Content of a Polyherbal Tea and Its Constituents. European J. Med. Plants 2015, 7 (4), 215-226.