p-Benzoquinone is used as a dienophile in Diels-Alder cycloadditions to prepare naphthoquinones and 1,4-phenanthrenediones. It acts as a dehydrogenation reagent and an oxidizer in synthetic organic chemistry. In the Thiele-Winter reaction, it is involved in the preparation of triacetate of hydroxyquinol by reacting with acetic anhydride and sulfuric acid. It is also used in the synthesis of bromadol and to suppress double- bond migration during olefin metathesis reactions. It is used as a precursor to hydroquinone which finds application in photography and as a reducing agent and an antioxidant in rubber production.
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-Benzoquinone is used as a dienophile in Diels-Alder cycloadditions to prepare naphthoquinones and 1,4-phenanthrenediones. It acts as a dehydrogenation reagent and an oxidizer in synthetic organic chemistry. In the Thiele-Winter reaction, it is involved in the preparation of triacetate of hydroxyquinol by reacting with acetic anhydride and sulfuric acid. It is also used in the synthesis of bromadol and to suppress double- bond migration during olefin metathesis reactions. It is used as a precursor to hydroquinone which finds application in photography and as a reducing agent and an antioxidant in rubber production.
Solubility
Soluble in water, ethanol, ether, methanol, benzene, acetone and ethyl acetate.
Notes
Light sensitive. Store in cool place. Incompatible and reacts violently with strong oxidizing agents.
RUO – Research Use Only
Mild reoxidant in palladium-catalyzed reactions, to convert Pd(0) back to Pd(II); see e.g.: Org. Synth. Coll., 8, 137 (1993). For use in the Pd-catalyzed oxidative addition of amines to electron-deficient alkenes, to give enamines, see Palladium(II) chloride, 11034. For the cis-1,4-stereo- and regioselective chloroacetoxylation of 1,3-dienes by Pd(OAc)2 and LiCl, in the presence of benzoquinone, see Palladium(II) acetate, 10516.
Reacts with allyl or isoprenyl tin derivatives in the presence of BF3 etherate to give ortho allyl-substituted quinones: Org. Synth. Coll., 9, 741 (1998). For a reaction scheme, see 2,3-Dimethoxy-5-methyl-1,4-benzoquinone, B24777.
Ajeel, M. A.; Aroua, M. K.; Daud, W. M. A. W. p-Benzoquinone Anodic Degradation by Carbon Black Diamond Composite Electrodes. Electrochim. Acta. 2015, 169, 46-51.
Papa, C. M.; Cesnik, A. J.; Evans, T. C.; Choi, K. S. Electrochemical Synthesis of Binary and Ternary Niobium-Containing Oxide Electrodes Using the p-Benzoquinone/Hydroquinone Redox Couple. Langmuir 2015, 31 (34), 9502-9510.