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Naphthoquinone

Names
Preferred IUPAC name Naphthalene-1,4-dione
Other names 1,4-Naphthoquinone Naphthoquinone α-Naphthoquinone
Identifiers
CAS Number	130-15-4
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL55934
ChemSpider	8215
ECHA InfoCard	100.004.526
PubChem CID	8530
UNII	RBF5ZU7R7K
CompTox Dashboard (EPA)	DTXSID5040704
InChI InChI=1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6HKey: FRASJONUBLZVQX-UHFFFAOYSA-N InChI=1/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6HKey: FRASJONUBLZVQX-UHFFFAOYAK
SMILES O=C1c2ccccc2C(=O)cc1
Properties
Chemical formula	C10H6O2
Molar mass	158.15 g/mol
Density	1.422 g/cm
Melting point	126 °C (259 °F; 399 K)
Boiling point	Begins to sublime at 100 °C
Solubility in water	0.09 g/L
Magnetic susceptibility (χ)	-73.5·10 cm/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

1,4-Naphthoquinone or para-naphthoquinone is a quinone 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.

Preparation

The industrial synthesis involves aerobic oxidation of naphthalene over a vanadium oxide catalyst:

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.

Reactions

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:

Uses

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.

Derivatives

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.

Other natural naphthoquinones include juglone, plumbagin, droserone.

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.

Naphthoquinone functions as a ligand through its electrophilic carbon-carbon double bonds.

Dichlone, a chlorinated derivative of 1,4-naphthoquinone, is used as a fungicide.

See also

• Hydroxynaphthoquinone
• 1,4-Benzoquinone
• Plumbagin
• Hooker reaction

References

1. Merck Index, 11th Edition, 6315.
2. Gaultier, J.; Hauw, C. (1965). "Structure de l'α-Naphtoquinone". Acta Crystallographica. 18 (2): 179–183. Bibcode:1965AcCry..18..179G. doi:10.1107/S0365110X65000439.
3. ^ Grolig, J.; Wagner, R. "Naphthoquinones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_067. ISBN 978-3527306732.
4. Braude, E. A.; Fawcett, J. S. (1953). "1,4-Naphthoquinone" (PDF). Organic Syntheses. 33: 50; Collected Volumes, vol. 4, p. 698.
5. M.A. Filatov; S. Baluschev; I.Z. Ilieva; V. Enkelmann; T. Miteva; K. Landfester; S.E. Aleshchenkov; A.V. Cheprakov (2012). "Tetraaryltetraanthraporphyrins: Synthesis, Structure, and Optical Properties". J. Org. Chem. 77 (24): 11119–11131. doi:10.1021/jo302135q. PMID 23205621.
6. 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.
7. Kündig, E. P.; Lomberget, T.; Bragg, R.; Poulard, C.; Bernardinelli, G. (2004). "Desymmetrization of a meso-Diol Complex Derived from : Use of New Diamine Acylation Catalysts". Chemical Communications. 2004 (13): 1548–1549. doi:10.1039/b404006f. PMID 15216374.

• 1,4-Naphthoquinones