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Revision as of 18:08, 18 February 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit		Latest revision as of 20:49, 22 February 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,042 edits Added bibcode. | Use this tool. Report bugs. | #UCB_Gadget
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	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 408415503		| verifiedrevid = 414651852
	| Reference=<ref>''Merck Index'', 11th Edition, '''6315'''.</ref>		| Reference =<ref>''Merck Index'', 11th Edition, '''6315'''.</ref>
⚫	| Name = Naphthoquinone
	| ImageFile = Naphthoquinone.png		| Name = Naphthoquinone
		⚫	| ImageFile = 1,4-Naphthoquinone.svg
	| ImageSize = 130
	| ImageFile1 = 1,4-Naphthoquinone-3D-balls.png		| ImageSize = 130
			| ImageFile1 = 1,4-Naphthoquinone-3D-balls.png
	| ImageSize1 = 180		| ImageSize1 = 180
	| ImageName1 = Ball-and-stick model		| ImageName1 = Ball-and-stick model
			| PIN = Naphthalene-1,4-dione <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->
	| IUPACName = 4a,8a-Dihydronaphthalene-1,4-dione
	| OtherNames = Naphthoquinone<br />1,4-Naphthoquinone<br />α-Naphthoquinone		| OtherNames = 1,4-Naphthoquinone<br />Naphthoquinone<br />α-Naphthoquinone
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| CASNo_Ref = {{cascite}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 130-15-4		| CASNo = 130-15-4
			| UNII_Ref = {{fdacite|correct|FDA}}
	| SMILES = O=C2C=CC(C1=CC=CC=C12)=O
			| UNII = RBF5ZU7R7K
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 55934
			| PubChem = 8530
			| ChemSpiderID = 8215
			| InChI = 1/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H
			| InChIKey = FRASJONUBLZVQX-UHFFFAOYAK
			| StdInChI = 1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H
			| StdInChIKey = FRASJONUBLZVQX-UHFFFAOYSA-N
			| SMILES = O=C1c2ccccc2C(=O)cc1
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>10</sub>H<sub>6</sub>O<sub>2</sub>		| Formula = C{{sub|10}}H{{sub|6}}O{{sub|2}}
	| MolarMass = 158.15 g/mol		| MolarMass = 158.15 g/mol
	| Density = 1.422 g/cm³		| Density = 1.422 g/cm{{sup|3}}
	| MeltingPt = 126 °C		| MeltingPtC = 126
	| BoilingPt = Begins to sublime at 100 °C		| MeltingPt_notes =
			| BoilingPt = Begins to sublime at 100 °C
	| Solubility = 0.09 g/L		| Solubility = 0.09 g/L
			| MagSus = -73.5·10{{sup|−6}} cm{{sup|3}}/mol
	}}		}}
	}}		}}
			'''1,4-Naphthoquinone''' or '''para-naphthoquinone''' is a ] derived from ]. It forms volatile yellow triclinic crystals and has a sharp odor similar to ]. It is almost insoluble in cold water, slightly soluble in ], and more soluble in polar organic solvents. In ] 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.<ref>{{ cite journal |author1=Gaultier, J. |author2=Hauw, C. | title = Structure de l'α-Naphtoquinone | journal = Acta Crystallographica | year = 1965 | volume = 18 | issue = 2 | pages = 179–183 | doi = 10.1107/S0365110X65000439 |bibcode=1965AcCry..18..179G }}</ref> It is an ] of ].
	'''Naphthoquinone''' is a class of ]s based on the C6-C4 skeleton.
			==Preparation==
	1,4-Naphthoquinone can be viewed as derivatives of ] through the replacement of two ] atoms by two ] groups.
			The industrial synthesis involves aerobic oxidation of naphthalene over a vanadium oxide catalyst:<ref name=Ullmann>{{ Ullmann | author = Grolig, J. | author2 = Wagner, R. | title = Naphthoquinones | doi = 10.1002/14356007.a17_067 }}</ref>
			:C{{sub|10}}H{{sub|8}} + 3/2 O{{sub|2}} → C{{sub|10}}H{{sub|6}}O{{sub|2}} + H{{sub|2}}O
			In the laboratory, naphthoquinone can be produced by the oxidation of a variety of naphthalene compounds. An inexpensive route involves oxidation of naphthalene with ].<ref>{{ OrgSynth | author = Braude, E. A. | author2 = Fawcett, J. S. | year = 1953 | title = 1,4-Naphthoquinone | volume = 33 | pages = 50 | collvol = 4 | collvolpages = 698 | prep = CV4P0698 | url = http://www.orgsyn.org/orgsyn/pdfs/CV4P0698.pdf }}</ref>
			==Reactions==
	The name is also used generically for two other ]s:
			1,4-Naphthoquinone acts as strong ] in ]. Its adduct with ] 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 ] at low temperature in the presence of 1 equivalent of ]:<ref>{{ cite journal | author = M.A. Filatov | author2 = S. Baluschev | author3 = I.Z. Ilieva| author4 = V. Enkelmann | author5 = T. Miteva| author6 = K. Landfester | author7 = S.E. Aleshchenkov | author8 = A.V. Cheprakov | title = Tetraaryltetraanthraporphyrins: Synthesis, Structure, and Optical Properties | journal = J. Org. Chem. | year = 2012 | volume = 77 | issue = 24 | pages = 11119–11131 | doi = 10.1021/jo302135q | pmid = 23205621 }}</ref>
	* ]
			]
	* ]
	* ] (''amphi''-naphthoquinone)
			==Uses==
	Naturally occurring naphtoquinones
			1,4-Naphthoquinone is mainly used as a precursor to ] by reaction with butadiene followed by oxidation. Nitration gives 5-nitro-1,4-naphthalenedione, precursor to an {{Not a typo|aminoanthroquinone}} that is used as a dye precursor.<ref name=Ullmann/>
	* ]
	* ]
	* ]
	==Properties==		==Derivatives==
		⚫	Naphthoquinone forms the central chemical structure of many natural compounds, most notably the ]. 2-Methyl-1,4-naphthoquinone, called ], is a more effective coagulant than vitamin K.
	1,4-Naphthoquinone forms yellow triclinic crystals and has an odor similar to ]. It is sparingly soluble in cold water, slightly soluble in ], and freely soluble in most polar organic solvents. In ] solutions it produces a reddish-brown color. Because of their aromatic stability, 1,4-naphthoquinone derivatives are known to possess anti-bacterial and anti-tumor properties.
			Other natural naphthoquinones include ], ], ].
⚫	Naphthoquinone forms the central chemical structure of many natural compounds, most notably the ].
		⚫	Naphthoquinone ] have significant pharmacological properties. They are ], they have significant ], ], ], ], ], and ] 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.<ref>{{ cite journal | last1 = Babula | first1 = P. | last2 = Adam | first2 = V. | last3 = Havel | first3 = L. | last4 = Kizek | first4 = R. |title = Naphthoquinones and their Pharmacological Properties | language = Czech | journal = Ceská a Slovenská Farmacie | year = 2007 | volume = 56 | issue = 3 | pages = 114–120 | pmid = 17867522 }}</ref>
	==Medicinal uses==
⚫	Naphthoquinone derivatives have significant pharmacological properties. They are ], they have significant ], ], ], ], ], and ] 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.<ref>{{cite journal | last1 = Babula | first1 = P | last2 = Adam | first2 = V | last3 = Havel | first3 = L | last4 = Kizek | first4 = R | title = Naphthoquinones and their pharmacological properties | journal = Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti | volume = 56 | issue = 3 | pages = 114–20 | year = 2007 | pmid = 17867522 }}</ref>
			Naphthoquinone functions as a ligand through its electrophilic carbon-carbon double bonds.<ref>{{ cite journal |author1=Kündig, E. P. |author2=Lomberget, T. |author3=Bragg, R. |author4=Poulard, C. |author5=Bernardinelli, G. | title = Desymmetrization of a ''meso''-Diol Complex Derived from <nowiki></nowiki>: Use of New Diamine Acylation Catalysts | journal = Chemical Communications | year = 2004 | volume = 2004 | issue = 13 | pages = 1548–1549 | doi = 10.1039/b404006f |pmid=15216374 }}</ref>
			], a chlorinated derivative of 1,4-naphthoquinone, is used as a fungicide.
	==See also==		==See also==
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	*]		*]
	*]		*]
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	==References==		==References==
			{{reflist}}
	<references/>
	{{Vitamin}}		{{Vitamin}}
	{{Natural phenol}}		{{Natural phenol}}
		⚫	{{DEFAULTSORT:Naphthoquinone, 1, 4-}}
	]		]
	]
	]
	]
	]
	]
	]
	]
⚫	]
	]