1,4-Naphthoquinone or para-naphthoquinone is an organic compound derived from naphthalene. It forms volatile yellow triclinic crystals and has a sharp odor similar to benzoquinone. It is almost insoluble in cold water, slightly soluble in petroleum ether, and more soluble in polar organic solvents. In alkaline solutions it produces a reddish-brown color. Vitamin K is a derivative of 1,4-naphthoquinone. It is a planar molecule with one aromatic ring fused to a quinone subunit. It is an isomer of 1,2-naphthoquinone.
|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||158.15 g/mol|
|Melting point||126 °C (259 °F; 399 K)|
|Boiling point||Begins to sublime at 100 °C|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
- C10H8 + 3/2 O2 → C10H6O2 + H2O
In the laboratory, naphthoquinone can be produced by the oxidation of a variety of naphthalene compounds. An inexpensive route involves oxidation of naphthalene with chromium trioxide.
1,4-Naphthoquinone acts as strong dienophile in Diels-Alder reaction. Its adduct with 1,3-butadiene can be prepared by two methods: 1) long (45 days) exposure of naphthoquinone in neat liquid butadiene taken in huge excess at room temperature in a thick-wall glass tube or 2) fast catalyzed cycloaddition at low temperature in the presence of 1 equivalent of tin(IV) chloride:
1,4-Naphthoquinone is mainly used as a precursor to anthraquinone by reaction with butadiene followed by oxidation. Nitration gives 5-nitro-1,4-naphthalenedione, precursor to an aminoanthroquinone that is used as a dye precursor.
Naphthoquinone forms the central chemical structure of many natural compounds, most notably the K vitamins. 2-Methyl-1,4-naphthoquinone, called menadione, is a more effective coagulant than vitamin K.
Naphthoquinone derivatives have significant pharmacological properties. They are cytotoxic, they have significant antibacterial, antifungal, antiviral, insecticidal, anti-inflammatory, and antipyretic properties. Plants with naphthoquinone content are widely used in China and the countries of South America, where they are used to treat malignant and parasitic diseases.
Dichlone, a chlorinated derivative of 1,4-naphthoquinone, is used as a fungicide.
- Merck Index, 11th Edition, 6315.
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- Braude, E. A.; Fawcett, J. S. (1953). "1,4-Naphthoquinone" (PDF). Organic Syntheses. 33: 50.; Collective Volume, 4, p. 698
- M.A. Filatov; S. Baluschev; I.Z. Ilieva; V. Enkelmann; T. Miteva; K. Landfester; S.E. Aleshchenkov; A.V. Cheprakov (2012). "Tetraaryltetraanthra[2,3]porphyrins: Synthesis, Structure, and Optical Properties". J. Org. Chem. 77 (24): 11119–11131. doi:10.1021/jo302135q.
- Babula, P.; Adam, V.; Havel, L.; Kizek, R. (2007). "Naphthoquinones and their Pharmacological Properties". Ceská a Slovenská Farmacie (in Czech). 56 (3): 114–120. PMID 17867522.
- Kündig, E. P.; Lomberget, T.; Bragg, R.; Poulard, C.; Bernardinelli, G. (2004). "Desymmetrization of a meso-Diol Complex Derived from [Cr(CO)3(η6-5,8-Naphthoquinone)]: Use of New Diamine Acylation Catalysts". Chemical Communications. 2004 (13): 1548–1549. doi:10.1039/b404006f.