1,4-Naphthoquinone

changed 414651852 Merck Index, 11th Edition, 6315. Naphthoquinone 1,4-Naphthoquinone.svg skin-invert-image 130 1,4-Naphthoquinone-3D-balls.png 180 Ball-and-stick model Naphthalene-1,4-dione 1,4-NaphthoquinoneNaphthoquinoneα-Naphthoquinone correct CAS 130-15-4 correct FDA RBF5ZU7R7K changed EBI 55934 8530 8215 1/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H FRASJONUBLZVQX-UHFFFAOYAK 1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H FRASJONUBLZVQX-UHFFFAOYSA-N O=C1c2ccccc2C(=O)cc1 C10H6O2 158.15 g/mol 1.422 g/cm3 126 Begins to sublime at 100 °C 0.09 g/L −73.5·10−6 cm3/mol 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. Natural vitamin K is a derivative of 1,4-naphthoquinone. It is a planar molecule with one aromatic ring fused to a quinone subunit.Gaultier, J. Hauw, C. Structure de l'α-Naphtoquinone Acta Crystallographica 1965 18 2 179–183 10.1107/S0365110X65000439 1965AcCry..18..179G 1,4-naphathoquinone itself has some vitamin K activity.Fernholz Erhard Ansbacher S. MacPhillamy H. B. The Vitamin K Activity of Naphthoquinones Journal of the American Chemical Society February 1940 62 2 430–432 10.1021/ja01859a052 It is an isomer of 1,2-naphthoquinone. Preparation The industrial synthesis involves aerobic oxidation of naphthalene over a vanadium oxide catalyst: Grolig, J. Wagner, R. Naphthoquinones 10.1002/14356007.a17_067 C10H8 + 3/2 O2 → C10H6O2 + H2O However, naphthoquinone rapidly oxidizes to phthalic anhydride under these conditions, and the latter is the major product.10.1007/s13203-018-0199-4 59 Applied Petrochemical Research 8 Autoxidation of aromatics Natalia Montoya Sánchez Arno de Klerk 6 September 2017 28 March 2018 free 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 Organic Syntheses Braude, E. A. Fawcett, J. S. 1953 33 50 10.15227/orgsyn.033.0050 free 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: M.A. Filatov S. Baluschev I.Z. Ilieva V. Enkelmann T. Miteva K. Landfester S.E. Aleshchenkov A.V. Cheprakov Tetraaryltetraanthra[2,3]porphyrins: Synthesis, Structure, and Optical Properties J. Org. Chem. 2012 77 24 11119–11131 10.1021/jo302135q 23205621 class=skin-invert-image|center|400 px|Diels-Alder reaction of 1,4-naphthoquinone with 1,3-butadiene Reduction of 1,4-naphthoquinone with dithionite gives 1,4-dihydroxynaphthalene. The reaction is reversible: oxidation of the diol give back the quinone.Booth Gerald Ullmann's Encyclopedia of Industrial Chemistry Naphthalene Derivatives 2000 10.1002/14356007.a17_009 978-3-527-30385-4 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. Naphthoquinone functions as a ligand through its electrophilic carbon-carbon double bonds.Kündig, E. P. Lomberget, T. Bragg, R. Poulard, C. Bernardinelli, G. Desymmetrization of a meso-Diol Complex Derived from [Cr(CO)3(η6-5,8-Naphthoquinone)]: Use of New Diamine Acylation Catalysts Chemical Communications 2004 2004 13 1548–1549 10.1039/b404006f 15216374 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. Some naphthoquinone derivatives 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. Babula P. Adam V. Havel L. Kizek R. Naphthoquinones and their Pharmacological Properties Czech Ceská a Slovenská Farmacie 2007 56 3 114–120 17867522 Natural 1,4-naphthoquinones thumb|right|upright|Chemical structure of juglone, a compound produced by black walnut trees. Alkannin, commercial red-brown dye from Alkanna tinctoria Dichlone, a chlorinated derivative of 1,4-naphthoquinone, a fungicide. Droserone, found in plants of the genus Plumbago Hexahydroxy-1,4-naphthalenedione Juglone, growth-stunting exudate of black walnut trees Lapachol, yellow irritant from lapacho tree Lawsone, dye in henna Menatetrenone, a polyhydroxylated 1,4-naphthoquinone found in some sea urchins 2-Methoxy-1,4-naphthoquinone, a compound found in Impatiens species Nigrosporin B, lightly studied compound found in the fungus Nigrospora sp Plumbagin, yellow toxin found in plants of the genus Plumbago Spinochrome B, a marine pigment Spinochrome D, a marine pigment Vitamin K and related compounds Phylloquinone Vitamin K2 Menadione (2-Methyl-1,4-naphthoquinone) Naphthazarin, red solid that occurs naturally and is earily prepared Synthetic 1,4-naphthoquinones Atovaquone, a drug Buparvaquone, an antiprotozoal drug used in veterinary medicine See also Hydroxynaphthoquinone 1,4-Benzoquinone Hooker reaction References Category:1,4-Naphthoquinones