Bucherer Carbazole Synthesis
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Bucherer Carbazole Synthesis
The Bucherer carbazole synthesis is a chemical reaction used to synthesize carbazoles from naphthols and aryl hydrazines using sodium bisulfite. The reaction is named after Hans Theodor Bucherer. See also * Borsche-Drechsel cyclization *Bucherer reaction The Bucherer reaction in organic chemistry is the reversible conversion of a naphthol to a naphthylamine in the presence of ammonia and sodium bisulfite. The reaction is widely used in the synthesis of dye precursors aminonaphthalenesulfonic ac ... References * * {{Organic reactions Nitrogen heterocycle forming reactions Heterocycle forming reactions Name reactions ...
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Hans Theodor Bucherer
Hans Theodor Bucherer (19 May 1869 – 29 May 1949) was a German chemist and gave name to several chemical reactions, for example the Bucherer carbazole synthesis, the Bucherer reaction, and the Bucherer–Bergs reaction Life Bucherer started studying chemistry at the University of Munich, University of Karlsruhe and later with Johannes Wislicenus at the University of Leipzig. After he received his Ph.D in 1893 he worked at BASF. He became professor at Technical University of Dresden in 1901 changed to the Technical University of Berlin in 1913 and became professor at the Technical University of Munich The Technical University of Munich (TUM or TU Munich; german: Technische Universität München) is a public research university in Munich, Germany. It specializes in engineering, technology, medicine, and applied and natural sciences. Establis ... in 1926. References 1869 births 1949 deaths 20th-century German chemists Academic staff of the Technical University o ...
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Chemical Reaction
A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the positions of electrons in the forming and breaking of chemical bonds between atoms, with no change to the Atomic nucleus, nuclei (no change to the elements present), and can often be described by a chemical equation. Nuclear chemistry is a sub-discipline of chemistry that involves the chemical reactions of unstable and radioactive Chemical element, elements where both electronic and nuclear changes can occur. The substance (or substances) initially involved in a chemical reaction are called reagent, reactants or reagents. Chemical reactions are usually characterized by a chemical change, and they yield one or more Product (chemistry), products, which usually have properties different from the reactants. Reactions often consist of a sequence o ...
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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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Hydrazine
Hydrazine is an inorganic compound with the chemical formula . It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly toxic unless handled in solution as, for example, hydrazine hydrate (). Hydrazine is mainly used as a foaming agent in preparing polymer foams, but applications also include its uses as a precursor to polymerization catalysts, pharmaceuticals, and agrochemicals, as well as a long-term storable propellant for in-space spacecraft propulsion. Additionally, hydrazine is used in various rocket fuels and to prepare the gas precursors used in air bags. Hydrazine is used within both nuclear and conventional electrical power plant steam cycles as an oxygen scavenger to control concentrations of dissolved oxygen in an effort to reduce corrosion. the world hydrazine hydrate market amounted to $350 million. About two million tons of hydrazine hydrate were used in foam blowing agents in 2015. Hydrazines r ...
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Sodium Bisulfite
Sodium bisulfite (or sodium bisulphite, sodium hydrogen sulfite) is a chemical mixture with the approximate chemical formula NaHSO3. Sodium bisulfite in fact is not a real compound, but a mixture of salts that dissolve in water to give solutions composed of sodium and bisulfite ions. It appears in form of white or yellowish-white crystals with an odor of sulfur dioxide. For properties of sodium bisulfite, refer to the table located to the right. Regardless of its ill-defined nature, sodium bisulfite is used in many different industries such a food additive with E number E222 in the food industry, a reducing agent in the cosmetic industry, and a decomposer of residual hypochlorite used in the bleaching industry. Synthesis Sodium bisulfite solutions can be prepared by treating a solution of suitable base, such as sodium hydroxide or sodium bicarbonate with sulfur dioxide. :SO2 + NaOH → NaHSO3 :SO2 + NaHCO3 → NaHSO3 + CO2 Attempts to crystallize the product yield Sodium me ...
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Bucherer Reaction
The Bucherer reaction in organic chemistry is the reversible conversion of a naphthol to a naphthylamine in the presence of ammonia and sodium bisulfite. The reaction is widely used in the synthesis of dye precursors aminonaphthalenesulfonic acids. :C10H7-2-OH + NH3 C10H7-2-NH2 + H2O The French chemist Robert Lepetit was the first to discover the reaction in 1898. The German chemist Hans Theodor Bucherer (1869–1949) discovered (independent from Lepetit) its reversibility and its potential especially in industrial chemistry. Bucherer published his results in 1904 and his name is connected to this reaction. The organic reaction also goes by the name Bucherer-Lepetit reaction or (wrongly) the Bucherer-Le Petit reaction. The reaction is used to convert 1,7-dihydroxynaphthalene into 7-amino-1-naphthol and 1-aminonaphthalene-4-sulfonic acid into 1-hydroxynaphthalene-4-sulfonic acid. It is also useful for transamination reactions of 2-aminonaphthalenes. Mechanism In ...
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Nitrogen Heterocycle Forming Reactions
Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at seventh in total abundance in the Milky Way and the Solar System. At standard temperature and pressure, two atoms of the element bond to form N2, a colorless and odorless diatomic gas. N2 forms about 78% of Earth's atmosphere, making it the most abundant uncombined element. Nitrogen occurs in all organisms, primarily in amino acids (and thus proteins), in the nucleic acids ( DNA and RNA) and in the energy transfer molecule adenosine triphosphate. The human body contains about 3% nitrogen by mass, the fourth most abundant element in the body after oxygen, carbon, and hydrogen. The nitrogen cycle describes the movement of the element from the air, into the biosphere and organic compounds, then back into the atmosphere. Many industrially important ...
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Heterocycle Forming Reactions
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different chemical element, 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 ...
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