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Trifluoroacetic Acid
Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula CF3CO2H. It is a structural analogue of acetic acid with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms and is a colorless liquid with a vinegar-like odor. TFA is a stronger acid than acetic acid, having an acid ionisation constant, ''K''a, that is approximately 34,000 times higher, as the highly electronegative fluorine atoms and consequent electron-withdrawing nature of the trifluoromethyl group weakens the oxygen-hydrogen bond (allowing for greater acidity) and stabilises the anionic conjugate base. TFA is widely used in organic chemistry for various purposes. Synthesis TFA is prepared industrially by the electrofluorination of acetyl chloride or acetic anhydride, followed by hydrolysis of the resulting trifluoroacetyl fluoride: : + 4 → + 3 + : + → + Where desired, this compound may be dried by addition of trifluoroacetic anhydride. An older ro ...
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Trifluoroacetate
Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula CF3CO2H. It is a structural analogue of acetic acid with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms and is a colorless liquid with a vinegar-like odor. TFA is a stronger acid than acetic acid, having an acid ionisation constant, ''K''a, that is approximately 34,000 times higher, as the highly electronegative Electronegativity, symbolized as , is the tendency for an atom of a given chemical element to attract shared electrons (or electron density) when forming a chemical bond. An atom's electronegativity is affected by both its atomic number and the ... fluorine atoms and consequent Electron-withdrawing functional group, electron-withdrawing nature of the trifluoromethyl group weakens the oxygen-hydrogen bond (allowing for greater acidity) and stabilises the anionic conjugate base. TFA is widely used in organic chemistry for various purposes. Synthesis TFA is pr ...
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CRC Handbook Of Chemistry And Physics
The ''CRC Handbook of Chemistry and Physics'' is a comprehensive one-volume reference resource for science research. First published in 1914, it is currently () in its 103rd edition, published in 2022. It is sometimes nicknamed the "Rubber Bible" or the "Rubber Book", as CRC originally stood for "Chemical Rubber Company". As late as the 1962–1963 edition (3604 pages) the ''Handbook'' contained myriad information for every branch of science and engineering. Sections in that edition include: Mathematics, Properties and Physical Constants, Chemical Tables, Properties of Matter, Heat, Hygrometric and Barometric Tables, Sound, Quantities and Units, and Miscellaneous. Earlier editions included sections such as "Antidotes of Poisons", "Rules for Naming Organic Compounds", "Surface Tension of Fused Salts", "Percent Composition of Anti-Freeze Solutions", "Spark-gap Voltages", "Greek Alphabet", "Musical Scales", "Pigments and Dyes", "Comparison of Tons and Pounds", "Twist Drill and St ...
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Sulfuric Acid
Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formula . It is a colorless, odorless and viscous liquid that is miscible with water. Pure sulfuric acid does not exist naturally on Earth due to its strong affinity to water vapor; it is hygroscopic and readily absorbs water vapor from the air. Concentrated sulfuric acid is highly corrosive towards other materials, from rocks to metals, since it is an oxidant with powerful dehydrating properties. Phosphorus pentoxide is a notable exception in that it is not dehydrated by sulfuric acid, but to the contrary dehydrates sulfuric acid to sulfur trioxide. Upon addition of sulfuric acid to water, a considerable amount of heat is released; thus the reverse procedure of adding water to the acid should not be performed since the heat released ...
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Organic Synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one of the most important branches of organic chemistry. There are several main areas of research within the general area of organic synthesis: '' total synthesis'', ''semisynthesis'', and ''methodology''. Total synthesis A total synthesis is the complete chemical synthesis of complex organic molecules from simple, commercially available petrochemical or natural precursors. Total synthesis may be accomplished either via a linear or convergent approach. In a ''linear'' synthesis—often adequate for simple structures—several steps are performed one after another until the molecule is complete; the chemical compounds made in each step are called synthetic intermediates. Most often, each step in a synthesis refers to a separate rea ...
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Reagent
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a substance ''consumed'' in the course of a chemical reaction. ''Solvents'', though involved in the reaction mechanism, are usually not called reactants. Similarly, '' catalysts'' are not consumed by the reaction, so they are not reactants. In biochemistry, especially in connection with enzyme-catalyzed reactions, the reactants are commonly called substrates. Definitions Organic chemistry In organic chemistry, the term "reagent" denotes a chemical ingredient (a compound or mixture, typically of inorganic or small organic molecules) introduced to cause the desired transformation of an organic substance. Examples include the Collins reagent, Fenton's reagent, and Grignard reagents. Analytical chemistry In analytical chemistry, a reag ...
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2,2,2-trifluoroethanol
2,2,2-Trifluoroethanol is the organic compound with the formula CF3CH2OH. Also known as TFE or trifluoroethyl alcohol, this colourless, water-miscible liquid has a smell reminiscent of ethanol. Due to the electronegativity of the trifluoromethyl group, this alcohol exhibits a stronger acidic character compared to ethanol. Synthesis Trifluoroethanol is produced industrially by hydrogenation or the hydride reduction of derivatives of trifluoroacetic acid, such as the esters or acyl chloride. TFE can also be prepared by hydrogenolysis of compounds of generic formula CF3−CHOH−OR (where R is hydrogen or an alkyl group containing from one to eight carbon atoms), in the presence of a palladium containing catalyst deposited on activated charcoal. As a co-catalyst for this conversion tertiary aliphatic amines like triethylamine are commonly employed. Uses Trifluoroethanol is used as a solvent in organic chemistry. Oxidations of sulfur compounds using hydrogen peroxide are effecti ...
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Trifluoroperacetic Acid
Trifluoroperacetic acid (trifluoroperoxyacetic acid, TFPAA) is an organofluorine compound, the peroxy acid analog of trifluoroacetic acid, with the condensed structural formula . It is a strong oxidizing agent for organic oxidation reactions, such as in Baeyer–Villiger oxidations of ketones. It is the most reactive of the organic peroxy acids, allowing it to successfully oxidise relatively unreactive alkenes to epoxides where other peroxy acids are ineffective. It can also oxidise the chalcogens in some functional groups, such as by transforming selenoethers to selones. It is a potentially explosive material and is not commercially available, but it can be quickly prepared as needed. Its use as a laboratory reagent was pioneered and developed by William D. Emmons. Properties At standard ambient temperature and pressure, trifluoroperacetic acid is a colourless liquid with a boiling point of 162 °C. It is soluble in acetonitrile, dichloromethane, diethyl ether, and sul ...
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Swarts Fluorination
Swarts fluorination is a process whereby the chlorine atoms in a compound – generally an organic compound, but experiments have been performed using silanes – are replaced with fluorine, by treatment with antimony trifluoride in the presence of chlorine or of antimony pentachloride. Some metal fluorides are particularly more useful than others, including silver(I) fluoride, mercurous fluoride, cobalt(II) fluoride and aforementioned antimony. Heating the mixture of the metal fluoride and the haloalkane (chlorine and bromine are replaced readily) yields the desired fluoro-alkane. In some particularly reactive cases, heating is unnecessary; shaking or stirring the reaction mixture is sufficient. This reaction has a good yield. The active species is antimony trifluorodichloride, which is produced in situ ''In situ'' (; often not italicized in English) is a Latin phrase that translates literally to "on site" or "in position." It can mean "locally", "on site", "on the premise ...
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Potassium Permanganate
Potassium permanganate is an inorganic compound with the chemical formula KMnO4. It is a purplish-black crystalline salt, that dissolves in water as K+ and , an intensely pink to purple solution. Potassium permanganate is widely used in the chemical industry and laboratories as a strong oxidizing agent, and also as a medication for dermatitis, for cleaning wounds, and general disinfection. It is on the World Health Organization's List of Essential Medicines. In 2000, worldwide production was estimated at 30,000 tonnes. Properties Potassium permanganate is the potassium salt of the tetrahedral transition metal oxo complex permanganate, in which four O2- ligands are bound to a manganese(VII) center. Structure KMnO4 forms orthorhombic crystals with constants: ''a'' = 910.5  pm, ''b'' = 572.0 pm, ''c'' = 742.5 pm. The overall motif is similar to that for barium sulfate, with which it forms solid solutions. In the solid (as in solution), each MnO4− centre is ...
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Trifluoroacetic Anhydride
Trifluoroacetic anhydride (TFAA) is the acid anhydride of trifluoroacetic acid. It is the perfluorinated derivative of acetic anhydride. Preparation Trifluoroacetic anhydride was originally prepared by the dehydration of trifluoroacetic acid with phosphorus pentoxide. The dehydration might also be carried out with excess α-halogenated acid chlorides. For example, with dichloroacetyl chloride: : 2 CF3COOH + Cl2CHCOCl → (CF3CO)2O + Cl2CHCOOH + HCl Uses Trifluoroacetic anhydride has various uses in organic synthesis. It may be used to introduce the corresponding trifluoroacetyl group, for which it is more convenient than the corresponding acyl chloride, trifluoroacetyl chloride, which is a gas. It can be used to promote reactions of carboxylic acids, including nucleophilic acyl substitution, Friedel-Crafts acylation, and acylation of other unsaturated compounds. Other electrophilic aromatic substitution reactions can also be promoted with trifluoroacetic anhydride, includ ...
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Acetic Anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air. Structure and properties Acetic anhydride, like most acid anhydrides, is a flexible molecule with a nonplanar structure. The pi system linkage through the central oxygen offers very weak resonance stabilization compared to the dipole-dipole repulsion between the two carbonyl oxygens. The energy barriers to bond rotation between each of the optimal aplanar conformations are quite low. Like most acid anhydrides, the carbonyl carbon atom of acetic anhydride has electrophilic character, as the leaving group is carboxylate. The internal asymmetry may contribute to acetic anhydride's potent electrophilicity as the asymmetric geome ...
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Acetyl Chloride
Acetyl chloride (CH3COCl) is an acyl chloride derived from acetic acid. It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl. Synthesis On an industrial scale, the reaction of acetic anhydride with hydrogen chloride produces a mixture of acetyl chloride and acetic acid: :(CH3CO)2O + HCl → CH3COCl + CH3CO2H Laboratory routes Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride. Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as PCl3, PCl5, SO2Cl2, phosgene, or SOCl2. However, these methods usually give acetyl chloride contaminated by phosphorus or sulfur impurities, which may interfere with the organic reactions. Other methods When heated, a mixture of dichloroacetyl chloride and acetic acid gives acetyl chloride. It can ...
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