Togni Reagent II
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Togni Reagent II
Togni reagent II (1-trifluoromethyl-1,2-benziodoxol-3(1''H'')-one) is a chemical compound used in organic synthesis for direct electrophilic trifluoromethylation. History Synthesis, properties, and reactivity of the compound were first described in 2006 by Antonio Togni and his coworkers at ETH Zurich. The article also contains information on Togni reagent I (1,3-dihydro-3,3-dimethyl-1-(trifluoromethyl)-1,2-benziodoxole). Preparation The synthesis consists of three steps. In the first step, 2-iodobenzoic acid is oxidized by sodium periodate and cyclized to 1-hydroxy-1,2-benziodoxol-3(1''H'')-one. The target compound can then be obtained by acylation with acetic anhydride and subsequent substitution reaction with trifluoromethyltrimethylsilane. Alternatively, trichloroisocyanuric acid can be used as oxidant in the place of sodium periodate for a newer one-pot synthesis method. Properties Physical properties The compound crystallized in a monoclinic crystal stru ...
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Chemical Compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element is therefore not a compound. A compound can be transformed into a different substance by a chemical reaction, which may involve interactions with other substances. In this process, bonds between atoms may be broken and/or new bonds formed. There are four major types of compounds, distinguished by how the constituent atoms are bonded together. Molecular compounds are held together by covalent bonds; ionic compounds are held together by ionic bonds; intermetallic compounds are held together by metallic bonds; coordination complexes are held together by coordinate covalent bonds. Non-stoichiometric compounds form a disputed marginal case. A chemical formula specifies the number of atoms of each element in a compound molecule, using the s ...
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Monoclinic Crystal System
In crystallography, the monoclinic crystal system is one of the seven crystal systems. A crystal system is described by three vectors. In the monoclinic system, the crystal is described by vectors of unequal lengths, as in the orthorhombic system. They form a parallelogram prism. Hence two pairs of vectors are perpendicular (meet at right angles), while the third pair makes an angle other than 90°. Bravais lattices Two monoclinic Bravais lattices exist: the primitive monoclinic and the base-centered monoclinic. For the base-centered monoclinic lattice, the primitive cell has the shape of an oblique rhombic prism;See , row mC, column Primitive, where the cell parameters are given as a1 = a2, α = β it can be constructed because the two-dimensional centered rectangular base layer can also be described with primitive rhombic axes. Note that the length a of the primitive cell below equals \frac \sqrt of the conventional cell above. Crystal classes The table below organ ...
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Catalysis
Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quickly, very small amounts of catalyst often suffice; mixing, surface area, and temperature are important factors in reaction rate. Catalysts generally react with one or more reactants to form intermediates that subsequently give the final reaction product, in the process of regenerating the catalyst. Catalysis may be classified as either homogeneous, whose components are dispersed in the same phase (usually gaseous or liquid) as the reactant, or heterogeneous, whose components are not in the same phase. Enzymes and other biocatalysts are often considered as a third category. Catalysis is ubiquitous in chemical industry of all kinds. Estimates are that 90% of all commercially produced chemical products involve catalysts at some s ...
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Copper
Copper is a chemical element with the symbol Cu (from la, cuprum) and atomic number 29. It is a soft, malleable, and ductile metal with very high thermal and electrical conductivity. A freshly exposed surface of pure copper has a pinkish-orange color. Copper is used as a conductor of heat and electricity, as a building material, and as a constituent of various metal alloys, such as sterling silver used in jewelry, cupronickel used to make marine hardware and coins, and constantan used in strain gauges and thermocouples for temperature measurement. Copper is one of the few metals that can occur in nature in a directly usable metallic form ( native metals). This led to very early human use in several regions, from circa 8000 BC. Thousands of years later, it was the first metal to be smelted from sulfide ores, circa 5000 BC; the first metal to be cast into a shape in a mold, c. 4000 BC; and the first metal to be purposely alloyed with another metal, tin, to create ...
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Alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, and Biological Chemistry'. 1232 pages. Two general types of monoalkenes are distinguished: terminal and internal. Also called α-olefins, terminal alkenes are more useful. However, the International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc. for cyclic ones; and "olefin" for the general class – cyclic or acyclic, with one or more double bonds. Acyclic alkenes, with only one double bond and no other functional groups (also known as mono-enes) form a homologous series of hydrocarbons with the general formula with '' ...
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Togni S Reagent II Reaction 02
Togni is an Italian surname, may refer to: * Camillo Togni, Italian composer * Darix Togni (1922–1976), Italian circus man *Eugênio Rômulo Togni (born 1982), retired Brazilian footballer and current football coach *Franco Togni (1960-2016), Italian male marathon runner and mountain runner * Gastón Alberto Togni (born 1997), Argentine professional football forward *Gianni Togni, Italian singer * Marco Togni, Italian Mathematician *Peter Togni, Canadian composer *Raul Togni Neto (born 1992), Brazilian professional basketball player * Rômulo Eugênio Togni, (born 1982) Brazilian footballer *Victor Togni Victor Togni (15 March 1935 - 29 March 1965) was a Swiss Canadian organist, improviser, composer, and teacher. His compositions received positive reception. He won first prize at the American Guild of Organists' Improvisation Competition on June ..., Swiss Canadian organist See also * Mamma Togni, an Italian dramatic monologue by Dario Fo and Franca Rame {{surname Italia ...
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Alcohol (chemistry)
In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl () functional group bound to a saturated carbon atom. The term ''alcohol'' originally referred to the primary alcohol ethanol (ethyl alcohol), which is used as a drug and is the main alcohol present in alcoholic drinks. An important class of alcohols, of which methanol and ethanol are the simplest examples, includes all compounds which conform to the general formula . Simple monoalcohols that are the subject of this article include primary (), secondary () and tertiary () alcohols. The suffix ''-ol'' appears in the IUPAC chemical name of all substances where the hydroxyl group is the functional group with the highest priority. When a higher priority group is present in the compound, the prefix ''hydroxy-'' is used in its IUPAC name. The suffix ''-ol'' in non-IUPAC names (such as paracetamol or cholesterol) also typically indicates that the substance is an alcohol. However, some compou ...
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Togni S Reagent II Reaction 01
Togni is an Italian surname, may refer to: * Camillo Togni, Italian composer * Darix Togni (1922–1976), Italian circus man *Eugênio Rômulo Togni (born 1982), retired Brazilian footballer and current football coach *Franco Togni (1960-2016), Italian male marathon runner and mountain runner * Gastón Alberto Togni (born 1997), Argentine professional football forward *Gianni Togni, Italian singer * Marco Togni, Italian Mathematician *Peter Togni, Canadian composer *Raul Togni Neto (born 1992), Brazilian professional basketball player * Rômulo Eugênio Togni, (born 1982) Brazilian footballer *Victor Togni Victor Togni (15 March 1935 - 29 March 1965) was a Swiss Canadian organist, improviser, composer, and teacher. His compositions received positive reception. He won first prize at the American Guild of Organists' Improvisation Competition on June ..., Swiss Canadian organist See also * Mamma Togni, an Italian dramatic monologue by Dario Fo and Franca Rame {{surname Italia ...
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Phenolates
Phenolates (also called phenoxides) are anions, salts, and esters of phenols. They may be formed by reaction of phenols with strong base. Properties Alkali metal phenolates, such as sodium phenolate hydrolyze in aqueous solution to form basic solutions. At pH = 10, phenol and phenolate are in approximately 1:1 proportions. Phenolate anions are enolates. As such, they react as nucleophiles at both oxygen and carbon positions. In general, reaction at oxygen occurs under kinetic control, whereas reaction at carbon occurs under thermodynamic control. Uses Alkyl aryl ethers can be synthesized through the Williamson ether synthesis by treating sodium phenolate with an alkyl halide: :C6H5ONa + CH3I → C6H5OCH3 + NaI :C6H5ONa + (CH3O)2SO2 → C6H5OCH3 + (CH3O)SO3Na Production of salicylic acid Salicylic acid is produced in the Kolbe–Schmitt reaction between carbon dioxide and sodium phenolate. : See also * Sodium phenolate Sodium phenoxide (sodium phenolate) is an organ ...
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Tetrahydrofuran
Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. Production About 200,000 tonnes of tetrahydrofuran are produced annually. The most widely used industrial process involves the acid-catalyzed dehydration of 1,4-butanediol. Ashland/ISP is one of the biggest producers of this chemical route. The method is similar to the production of diethyl ether from ethanol. The butanediol is derived from condensation of acetylene with formaldehyde followed by hydrogenation. DuPont developed a process for producing THF by oxidizing ''n''-butane to crude maleic anhydride, followed by catalytic hydrogenation. A third major industrial route entails hydroformylation of allyl alcohol followed by ...
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Acetonitrile
Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula and structure . This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not classed as organic). It is produced mainly as a byproduct of acrylonitrile manufacture. It is used as a polar aprotic solvent in organic synthesis and in the purification of butadiene. The skeleton is linear with a short distance of 1.16  Å. Acetonitrile was first prepared in 1847 by the French chemist Jean-Baptiste Dumas. Applications Acetonitrile is used mainly as a solvent in the purification of butadiene in refineries. Specifically, acetonitrile is fed into the top of a distillation column filled with hydrocarbons including butadiene, and as the acetonitrile falls down through the column, it absorbs the butadiene which is then sent from the bottom of the tower to a second separating tower. Heat is then employed in the separatin ...
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Trifluoroiodomethane
Trifluoroiodomethane, also referred to as trifluoromethyl iodide is a halomethane with the formula CF3I. It is an experimental alternative to Halon 1301 (CBrF3) in unoccupied areas. It would be used as a gaseous fire suppression flooding agent for in-flight aircraft and electronic equipment fires. Chemistry It is used in the rhodium-catalyzed α- trifluoromethylation of α,β-unsaturated ketones. It can be used as a new generation fire extinguishing agent to replace Halon in fire protection systems. The mechanism of extinguishing fires for CF3I is active and primarily based on interruption of the chain reaction in the combustion area of the flame by so-called "negative" catalytic action. It is also used as an eco-friendly insulation gas to replace SF6 in electrical power industry. In the presence of sunlight or at temperatures above 100 °C it can react with water, forming hazardous by-products such as hydrogen fluoride (HF), hydrogen iodide (HI) and carbonyl fluoride (CO ...
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