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5,8-Dihydroxy-1,4-naphthoquinone
Naphthazarin, often called 5,8-dihydroxy-1,4-naphthoquinone or 5,8-dihydroxy-1,4-naphthalenedione (IUPAC), is a naturally occurringThomson R.H. Naturally Occurring Quinones. Academic Press, London (1971). Quoted by Khalafy and Bruce.Thomson R.H. Naturally Occurring Quinones III. Chapman and Hall, London (1987). Quoted by Khalafy and Bruce. organic compound with formula , formally derived from 1,4-naphthoquinone through replacement of two hydrogen atoms by hydroxyl (OH) groups. It is thus one of many dihydroxynaphthoquinone structural isomers. Naphthazarin is soluble in 1,4-dioxane from which it crystallizes as deep red needles that melt at 228−232 °C. Synthesis Naphtharazin can be prepared by condensation of 1,4-dimethoxybenzene with 2,3-dichloromaleic anhydride followed by reductive dechlorination and reoxidation.Lewis J.R. and Paul J.J.(1977). Z. Naturforsch., B, 32: 1473. Quoted by Khalafy and Bruce.Huot R. and Brassard P. (1974). Can. J. Chem., 52: 838. Quoted ...
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Dihydroxynaphthoquinone
A dihydroxynaphthoquinone (formula: ) is any of several organic compounds that can be viewed as derivatives of naphthoquinone through replacement of two hydrogen atoms (H) by hydroxyl groups (OH). The unqualified term "dihydroxynaphthoquinone" usually means a derivative of 1,4-naphthoquinone. Other dihydroxy- compounds can be derived from the two other known isomers, 1,2-naphthoquinone (''ortho''-) and 2,6-naphthoquinone (''amphi''-). Isomers From 1,4-naphthoquinone Due to the symmetry of the parent quinone, there are only nine distinct isomers of dihydroxy-1,4-naphthoquinone: * 2,3-Dihydroxy-1,4-naphthoquinone. * 2,5-Dihydroxy-1,4-naphthoquinone. * 2,6-Dihydroxy-1,4-naphthoquinone. * 2,7-Dihydroxy-1,4-naphthoquinone. * 2,8-Dihydroxy-1,4-naphthoquinone. * 5,6-Dihydroxy-1,4-naphthoquinone. * 5,7-Dihydroxy-1,4-naphthoquinone. * 5,8-Dihydroxy-1,4-naphthoquinone (naphthazarin). J. Khalafy and J.M. Bruce (2002), ''Oxidative dehydrogenation of 1-tetralones: Synthesis of juglone, na ...
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IUPAC
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is a member of the International Science Council (ISC). IUPAC is registered in Zürich, Switzerland, and the administrative office, known as the "IUPAC Secretariat", is in Research Triangle Park, North Carolina, United States. This administrative office is headed by IUPAC's executive director, currently Lynn Soby. IUPAC was established in 1919 as the successor of the International Congress of Applied Chemistry for the advancement of chemistry. Its members, the National Adhering Organizations, can be national chemistry societies, national academies of sciences, or other bodies representing chemists. There are fifty-four National Adhering Organizations and three Associate National Adhering Organizations. IUPAC's Inter-divisional Committee on ...
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Dechlorination
In organochlorine chemistry, reductive dechlorination describes any chemical reaction which cleaves the covalent bond between carbon and chlorine via reductants, to release chloride ions. Many modalities have been implemented, depending on the application. Reductive dechlorination is often applied to remediation of chlorinated pesticides or dry cleaning solvents. It is also used occasionally in the synthesis of organic compounds, e.g. as pharmaceuticals. Chemical Dechlorination is a common reaction in organic synthesis. Usually only stoichiometric amounts of dechlorinating agent are used. A classic Ullmann reaction is the conversion of 2-chloronitrobenzene into 2,2'-dinitrobiphenyl with a copper - bronze alloy. Other examples: *Zerovalent iron * Organophosphorus(III) compounds effect gentle dechlorinations. The products are alkenes and phosphorus(V). *Alkaline earth metals and zinc are used for more difficult dechlorinations. The side product is zinc chloride. Biological ...
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Hydroquinones
Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''para'' position. It is a white granular solid. Substituted derivatives of this parent compound are also referred to as hydroquinones. The name "hydroquinone" was coined by Friedrich Wöhler in 1843. Production Hydroquinone is produced industrially in two main ways.Phillip M. Hudnall "Hydroquinone" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. 2005 Wiley-VCH, Weinheim. . * The most widely used route is similar to the cumene process in reaction mechanism and involves the dialkylation of benzene with propene to give 1,4-diisopropylbenzene. This compound reacts with air to afford the bis(hydroperoxide), which is structurally similar to cumene hydroperoxide and rearranges in acid to give acetone and hydroquinone. * A sec ...
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Manganese Dioxide
Manganese dioxide is the inorganic compound with the formula . This blackish or brown solid occurs naturally as the mineral pyrolusite, which is the main ore of manganese and a component of manganese nodules. The principal use for is for dry-cell batteries, such as the alkaline battery and the zinc–carbon battery.. is also used as a pigment and as a precursor to other manganese compounds, such as . It is used as a reagent in organic synthesis, for example, for the oxidation of allylic alcohols. is α polymorph that can incorporate a variety of atoms (as well as water molecules) in the "tunnels" or "channels" between the manganese oxide octahedra. There is considerable interest in as a possible cathode for lithium-ion batteries. Structure Several polymorphs of are claimed, as well as a hydrated form. Like many other dioxides, crystallizes in the rutile crystal structure (this polymorph is called pyrolusite or ), with three-coordinate oxide and octahedral metal centres. ...
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Oxidation
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a decrease in the oxidation state. There are two classes of redox reactions: * ''Electron-transfer'' – Only one (usually) electron flows from the reducing agent to the oxidant. This type of redox reaction is often discussed in terms of redox couples and electrode potentials. * ''Atom transfer'' – An atom transfers from one substrate to another. For example, in the rusting of iron, the oxidation state of iron atoms increases as the iron converts to an oxide, and simultaneously the oxidation state of oxygen decreases as it accepts electrons released by the iron. Although oxidation reactions are commonly associated with the formation of oxides, other chemical species can serve the same function. In hydrogenation, C=C (and other) bonds ar ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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1,4-dioxane
1,4-Dioxane () is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers ( 1,2- and 1,3-) are rarely encountered. Dioxane is used as a solvent for a variety of practical applications as well as in the laboratory, and also as a stabilizer for the transport of chlorinated hydrocarbons in aluminum containers.Wisconsin Department of Health Services (20131,4-Dioxane Fact Sheet Publication 00514. Accessed 2016-11-12. Synthesis Dioxane is produced by the acid-catalysed dehydration of diethylene glycol, which in turn is obtained from the hydrolysis of ethylene oxide. In 1985, the global production capacity for dioxane was between 11,000 and 14,000 tons. In 1990, the total U.S. production volume of dioxane was between 5,250 and 9,150 tons. Structure The dioxane molecule is centrosymmetric, meaning that it adopts a chai ...
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