1,4-Benzoquinone

1,4-Benzoquinone is the chemical compound with the formula C₆H₄O₂. This nonaromatic six-membered ring compound is the oxidized derivative of 1,4-hydroquinone.^[1] The molecule is multifunctional: it exhibits properties of a ketone, forming an oxime; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions.

Additional recommended knowledge

Essential Laboratory Skills Guide

What is the Correct Way to Check Repeatability in Balances?

Recognize and detect the effects of electrostatic charges on your balance

Applications in organic synthesis

It is used as a hydrogen acceptor and oxidant in organic synthesis.^[2] 1,4-Benzoquinone serves as a dehydrogenation reagent. It is also uses as a dienophile in Diels Alder reactions.^[3]

Related 1,4-benzoquinones

A variety of derivatives and analogues are known. Illustrative examples:

• 1,4-Naphthoquinone, derived by oxidation of naphthalene with chromium trioxide.^[4]
• 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, a stronger oxidant and dehydrogenation agent than 1,4-benzoquinone.^[5]
• Ubiquinone-1, a naturally occurring 1,4-benzoquinone.
• Chloro-p-benzoquinone, (CAS no. [695-99-8])^[6]
• Chloranil, 1,4-C₆Cl₄O₂, a stronger oxidant and dehydrogenation agent than 1,4-benzoquinone.

See also

• 1,2-Benzoquinone
• Quinones

References

1. ^ H. W. Underwood, Jr. and W. L. Walsh (1943). "Quinone". Org. Synth.; Coll. Vol. 2: 553. 
2. ^ Yang, T.-K.; Shen, C.-Y. ”1,4-Benzoquinone” in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289.
3. ^ Oda, M.; Kawase, T.; Okada, T.; Enomoto, T. (1998). "2-Cyclohexene-1,4-dione". Org. Synth.; Coll. Vol. 9: 186. 
4. ^ E. A. Braude E. A.; Fawcett, J. S. (1963). "1,4-Naphthoquinone". Org. Synth.; Coll. Vol. 4: 698. 
5. ^ Vogel, E.; Klug, W.; Breuer, A. (1988). "1,6-Methano[10]annulene". Org. Synth.; Coll. Vol. 6: 731. 
6. ^ Harman, R. E. (1963). "Chloro-p-benzoquinone". Org. Synth.; Coll. Vol. 4: 148.