1,4-benzoquinone
Also known as p-benzoquinone, p-BQ, benzo-1,4-quinone, benzoquinone, Quinone, p-quinone, 1,4-Cyclohexadienedione, Cyclohexadienedione
1,4-Benzoquinone, commonly known as '''para-quinone''', is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone
Chemical data
- Formula
- C6H4O2
- Molecular weight
- 108.09 g/mol
- IUPAC name
- cyclohexa-2,5-diene-1,4-dione
- SMILES
- C1=CC(=O)C=CC1=O
- InChIKey
- AZQWKYJCGOJGHM-UHFFFAOYSA-N
- XLogP
- 0.2
- Polar surface area
- 34.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
32,756 papersArticle
9 sectionsContents
- Preparation
- Structure and redox
- Reactions and applications
- Organic synthesis
- Related 1,4-benzoquinones
- Metabolism
- Safety
- See also
- References
1,4-Benzoquinone, commonly known as '''para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.
==Preparation== 1,4-Benzoquinone is prepared industrially by oxidation of hydroquinone, which can be obtained by several routes. One route involves oxidation of diisopropylbenzene and the Hock rearrangement. The net reaction can be represented as follows: C6H4(CHMe2)2 + 3 O2 -> C6H4O2 + 2 OCMe2 + H2O The reaction proceeds via the bis(hydroperoxide) and the hydroquinone. Acetone is a coproduct.