Pigment Violet 23
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Pigment Violet 23
Pigment violet 23 is an organic compound that is a commercial pigment. It is member of the dioxazine family of heterocyclic compounds, but derived from carbazoles. It is prepared by condensation of chloranil and 3-amino-''N''-ethylcarbazole. It has a centrosymmetric angular structure. For many years, the structure was assigned, incorrectly, as having a "linear structure" (European Community number, EC no. 228-767-9, CAS RN 6358-30-1) which differ in terms of the carbazole ring fusion. Pigment violet 23 is prepared by condensation of an aniline with chloranil.Horst Tappe, Walter Helmling, Peter Mischke, Karl Rebsamen, Uwe Reiher, Werner Russ, Ludwig Schläfer and Petra Vermehren "Reactive Dyes"in Ullmann's Encyclopedia of Industrial Chemistry 2000, Wiley-VCH, Weinheim. {{doi, 10.1002/14356007.a22_651 References Organic pigments ...
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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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Pigment
A pigment is a colored material that is completely or nearly insoluble in water. In contrast, dyes are typically soluble, at least at some stage in their use. Generally dyes are often organic compounds whereas pigments are often inorganic compounds. Pigments of prehistoric and historic value include ochre, charcoal, and lapis lazuli. Economic impact In 2006, around 7.4 million tons of inorganic, organic, and special pigments were marketed worldwide. Estimated at around US$14.86 billion in 2018 and will rise at over 4.9% CAGR from 2019 to 2026. The global demand for pigments was roughly US$20.5 billion in 2009. According to an April 2018 report by ''Bloomberg Businessweek'', the estimated value of the pigment industry globally is $30 billion. The value of titanium dioxide – used to enhance the white brightness of many products – was placed at $13.2 billion per year, while the color Ferrari red is valued at $300 million each year. Physical principles ...
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Oxazine
Oxazines are heterocyclic compounds containing one oxygen and one nitrogen atom in a doubly unsaturated six-membered ring. Isomers exist depending on the relative position of the heteroatoms and relative position of the double bonds. By extension, the derivatives are also referred to as oxazines; examples include ifosfamide and morpholine (tetrahydro-1,4-oxazine). A commercially available dihydro-1,3-oxazine is a reagent in the Meyers synthesis of aldehydes. Fluorescent dyes such as Nile red and Nile blue are based on the aromatic benzophenoxazine. Cinnabarine and cinnabaric acid are two naturally occurring dioxazines, being derived from biodegradation of tryptophan. Dioxazines Dioxazines are pentacyclic compounds consisting of two oxazine subunits. A commercially important example is the pigment pigment violet 23. Benzoxazines Benzoxazines are bicyclic compounds formed by the ring fusion of a benzene ring with an oxazine. Polybenzoxazines are a class of polymers formed by th ...
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Heterocyclic Compound
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles. Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles. 59% of US FDA-approved drugs contain nitrogen heterocycles. Classification The study of heterocyclic chemistry focuses especially on unsaturated derivatives, and the preponderance of work and applications involves unstrained 5- and 6-membered rings. Included are pyridine, thiophene, pyrrole, and furan. Another large class of heterocycles refers to those fused to benzene rings. For example, the fused benzene derivatives of pyridine, thiophene, pyrrole, and furan are quinol ...
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Carbazole
Carbazole is an aromatic heterocyclic organic compound. It has a tricyclic structure, consisting of two six-membered benzene rings fused on either side of a five-membered nitrogen-containing ring. The compound's structure is based on the indole structure, but in which a second benzene ring is fused onto the five-membered ring at the 2–3 position of indole (equivalent to the 9a–4a double bond in carbazole, respectively). Carbazole is a constituent of tobacco smoke. Synthesis A classic laboratory organic synthesis for carbazole is the Borsche–Drechsel cyclization. In the first step, phenylhydrazine is condensed with cyclohexanone to the corresponding imine. The second step is a hydrochloric acid-catalyzed rearrangement reaction and ring-closing reaction to tetrahydrocarbazole. In one modification, both steps are rolled into one by carrying out the reaction in acetic acid. In the third step, this compound is oxidized by red lead to carbazole itself. Another classic is ...
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Chloranil
Chloranil is a quinone with the molecular formula C6Cl4O2. Also known as tetrachloro-1,4-benzoquinone, it is a yellow solid. Like the parent benzoquinone, chloranil is a planar molecule J.-M. Lü, S. V. Rosokha, I. S. Neretin and J. K. Kochi, "Quinones as Electron Acceptors. X-Ray Structures, Spectral (EPR, UV-vis) Characteristics and Electron-Transfer Reactivities of Their Reduced Anion Radicals as Separated vs Contact Ion Pairs" Journal of the American Chemical Society 2006 128, 16708-16719. that functions as a mild oxidant. Synthesis and use as reagent Chloranil is produced by chlorination of phenol to give hexachlorocyclohexa-2,5-dien-1-one ("hexachlorophenol"). Hydrolysis of the dichloromethylene group in this dienone gives chloranil: :C6H5OH + 6 Cl2 → C6Cl6O + 6 HCl :C6Cl6O + H2O → C6Cl4O2 + 2 HCl Chloroanil serves as a hydrogen acceptor. It is more electrophilic than quinone itself. It is used for the aromatization reactions, such as the conversion of cy ...
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European Community Number
The European Community number (EC number) is a unique seven-digit identifier that was assigned to substances for regulatory purposes within the European Union by the European Commission. The ''EC Inventory'' comprises three individual inventories, EINECS, ELINCS and the NLP list. Structure The EC number may be written in a general form as: NNN-NNN-R, where R is a check digit and N represents integers. The check digit is calculated using the ISBN method. According to this method, the check digit R is the following sum modulo 11: :R = (N_1 + 2 N_2 + 3N_3 + 4N_4 + 5N_5 + 6N_6) \bmod 11 If the remainder R is equal to 10, that combination of digits is not used for an EC number. To illustrate, the EC number of dexamethasone is 200-003-9. N1 is 2, N2 through N5 are 0, and N6 is 3. :\frac = \frac = 1 + \frac The remainder is 9, which is the check digit. There is a set of 181 ELINCS numbers (EC numbers starting with 4) for which the checksum by the above algorithm is 10 and the ...
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Ring Fusion
In organic chemistry annulation (from the Latin ''anellus'' for "little ring"; occasionally annelation) is a chemical reaction in which a new ring is constructed on a molecule. : Examples are the Robinson annulation, Danheiser annulation and certain cycloadditions. Annular molecules are constructed from side-on condensed cyclic segments, for example helicenes and acenes. In transannulation a bicyclic molecule is created by intramolecular carbon-carbon bond formation in a large monocyclic ring. An example is the samarium(II) iodide induced ketone - alkene cyclization of ''5-methylenecyclooctanone'' which proceeds through a ketyl intermediate: : Benzannulation The term benzannulated compounds refers to derivatives of cyclic compounds (usually aromatic) which are fused to a benzene ring. Examples are listed in the table below: In contemporary chemical literature, the term benzannulation also means "construction of benzene rings from acyclic precursors". upright=1.4, Protonatio ...
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