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Picoline
Picoline refers to any of three isomers of methylpyridine (CH3C5H4N). They are all colorless liquids with a characteristic smell similar to that of pyridine. They are miscible with water and most organic solvents. The CAS number of an unspecified picoline isomer is 333-41-1 The methyl group in 2- and 4- picolines is reactive; e.g., 2-picolines condenses with acetaldehyde in the presence of warm aqueous sodium hydroxide to form 2-propenylpyridine. History Picoline was obtained, in impure form, in 1826 by the German chemist Otto Unverdorben (1806 – 1873), who obtained it by the pyrolysis (roasting) of bones. He called it ''Odorin'' due to its unpleasant smell. In 1849, the Scottish chemist Thomas Anderson (1819 – 1874) prepared picoline in pure form, from coal tar and via the pyrolysis of bones. Anderson also named picoline by combining the Latin words ''pix'' (tar) and ''oleum'' (oil) because coal tar oil was a source of picoline. By 1870, the German chemist Adolf von Ba ...
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2-Methylpyridine
2-Methylpyridine, or 2-picoline, is the compound described with formula C6H7N. 2-Picoline is a colorless liquid that has an unpleasant odor similar to pyridine. It is mainly used to make vinylpyridine and the agrichemical nitrapyrin. Synthesis 2-Picoline was the first pyridine compound reported to be isolated in pure form. It was isolated from coal tar in 1846 by T. Anderson. This chemistry was practiced by Reilly Industries. It is now mainly produced by two principal routes. One method involves the condensation of acetaldehyde and ammonia in the presence of an oxide catalyst. This method affords a mixture of 2- and 4-picolines: : Another method involves the condensation of acetone and acrylonitrile to give 5-oxohexanenitrile, which then cyclizes to give 2-picoline. Approximately 8000 t/a was produced worldwide in 1989. Reactions Most of the reactions of picoline are centered on the methyl group. For example, the principal use of 2-picoline is as a precursor of 2-vinylpyrid ...
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Pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow, due to the formation of extended, unsaturated polymeric chains, which show significant electrical conductivity. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. As of 2016, it is synthesized on the scale of about 20,000 tons per year worldwide. Properties Physical properties The molecular electric dipole moment is 2.2 debyes. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase ...
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3-Methylpyridine
3-Methylpyridine or 3-picoline, is an organic compound with formula 3-CH3C5H4N. It is one of three positional isomers of methylpyridine, whose structures vary according to where the methyl group is attached around the pyridine ring. This colorless liquid is a precursor to pyridine derivatives that have applications in the pharmaceutical and agricultural industries. Like pyridine, 3-methylpyridine is a colorless liquid with a strong odor and is classified as a weak base. Synthesis 3-Methylpyridine is produced industrially by the reaction of acrolein, with ammonia. These ingredients are combined as gases which flows over an oxide-based heterogeneous catalyst. The reaction is multistep, culminating in cyclisation. :2 CH2CHCHO + NH3 → CH3C5H4N + 2H2O This process also affords substantial amounts of pyridine, which arises by demethylation of the 3-methylpyridine. A route that gives better control of the product starts with acrolein, propionaldehyde, and ammonia: :CH2CHCHO ...
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Thomas Anderson (chemist)
Thomas Anderson (2 July 1819 – 2 November 1874) was a 19th-century Scottish chemist. In 1853 his work on alkaloids led him to discover the correct formula/composition for codeine., In 1868 he discovered pyridine and related organic compounds such as picoline through studies on the distillation of bone oil and other animal matter. As well as his work on organic chemistry, Anderson made important contributions to agricultural chemistry, writing over 130 reports on soils, fertilisers and plant diseases. He kept abreast of all areas of science, and was able to advise his colleague Joseph Lister on Pasteur's germ theory and the use of carbolic acid as an antiseptic. Biographys Born in Leith, Thomas Anderson graduated from the University of Edinburgh with a medical doctorate in 1841. Having developed an interest in chemistry during his medical studies, he then spent several years studying chemistry in Europe, including spells under Jöns Jakob Berzelius in Sweden and Jus ...
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Pyridinium
Pyridinium refers to the cation . It is the conjugate acid of pyridine. Many related cations are known involving substituted pyridines, e.g. picolines, lutidines, collidines. They are prepared by treating pyridine with acids. As pyridine is often used as an organic base in chemical reactions, pyridinium salts are produced in many acid-base reactions. Its Salt (chemistry), salts are often insoluble in the organic solvent, so Precipitation (chemistry), precipitation of the pyridinium leaving group complex is an indication of the progress of the reaction. Pyridinium cations are aromatic, as determined through Hückel's rule. They are isoelectronic with benzene. ''N''-Alkylpyridinium cations When the acidic proton is replaced by alkyl, the compounds are called ''N''-alkylpyridinium. A simple representative is Methylpyridinium, ''N''-methylpyridinium ([C5H5NCH3]+). These pyridinium intermediates have been used as electrophiles in synthetic organic chemistry to build dearomatized ...
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4-Methylpyridine
4-Methylpyridine is the organic compound with the formula CH3C5H4N. It is one of the three isomers of methylpyridine. This pungent liquid is a building block for the synthesis of other heterocyclic compounds. Its conjugate acid, the 4-methylpyridinium ion, has a p''K''a of 5.98, about 0.7 units above that of pyridine itself. Production and uses 4-Methylpyridine is both isolated from coal tar and is synthesized industrially. It forms via the reaction of acetaldehyde and ammonia in the presence of an oxide catalyst. The method also affords some 2-methylpyridine. 4-Methylpyridine is of little intrinsic value but is a precursor to other commercially significant species, often of medicinal interest. For example, ammoxidation of 4-methylpyridine gives 4-cyanopyridine, the precursor to a variety of other derivatives such as the antituberculosis drug isoniazid. Toxicity Like most alkylpyridines, the LD50 In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50% ...
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4-Picoline Structural Formula V1
4-Methylpyridine is the organic compound with the formula CH3C5H4N. It is one of the three isomers of methylpyridine. This pungent liquid is a building block for the synthesis of other heterocyclic compounds. Its conjugate acid, the 4-methylpyridinium ion, has a p''K''a of 5.98, about 0.7 units above that of pyridine itself. Production and uses 4-Methylpyridine is both isolated from coal tar and is synthesized industrially. It forms via the reaction of acetaldehyde and ammonia in the presence of an oxide catalyst. The method also affords some 2-methylpyridine. 4-Methylpyridine is of little intrinsic value but is a precursor to other commercially significant species, often of medicinal interest. For example, ammoxidation of 4-methylpyridine gives 4-cyanopyridine, the precursor to a variety of other derivatives such as the antituberculosis drug isoniazid. Toxicity Like most alkylpyridines, the LD50 In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50% ...
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Niacin (substance)
Niacin, also known as nicotinic acid, is an organic compound and a form of vitamin B3, an essential human nutrient. It can be manufactured by plants and animals from the amino acid tryptophan. Niacin is obtained in the diet from a variety of whole and processed foods, with highest contents in fortified packaged foods, meat, poultry, red fish such as tuna and salmon, lesser amounts in nuts, legumes and seeds. Niacin as a dietary supplement is used to treat pellagra, a disease caused by niacin deficiency. Signs and symptoms of pellagra include skin and mouth lesions, anemia, headaches, and tiredness. Many countries mandate its addition to wheat flour or other food grains, thereby reducing the risk of pellagra. The amide derivative nicotinamide (niacinamide) is a component of the coenzymes nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP+). Although niacin and nicotinamide are identical in their vitamin activity, nicotinamide doe ...
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Wilhelm Körner
Wilhelm Körner, later a.k.a. Guglielmo Körner (April 20, 1839 in Cassel – March 29, 1925 in Milan), was a German chemist. Life Körner studied chemistry at Giessen, where he graduated in 1860. In 1866, he became assistant to Kekulé at Ghent. In 1867, when Kekulé was called to Bonn, Körner left Ghent for Palermo where entered the laboratory of Stanislao Cannizzaro, and occupied himself with the study of the aromatic compounds. Besides his work on aromatic compounds, his interest in botany led him to the study of many vegetable substances. In 1870, he accepted the chair of organic chemistry at "Scuola Superiore di Agricoltura" ("School of Agriculture", University of Milan The University of Milan ( it, Università degli Studi di Milano; la, Universitas Studiorum Mediolanensis), known colloquially as UniMi or Statale, is a public research university in Milan, Italy. It is one of the largest universities in Europe ...), where he retained until 1922, when for reasons ...
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Methyl Group
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, bounded to the rest of the molecule by a single covalent bond (), it can be found on its own in any of three forms: methanide anion (), methylium cation () or methyl radical (). The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed. Methyl cation, anion, and radical Methyl cation The methylium cation () exists in the gas phase, but is otherwise not encountered. Some compounds are considered to be sources of the cation, and this simplification is used pervasively in organic chemistry. For example, protonation of methanol gives an elect ...
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Calcium Oxide
Calcium oxide (CaO), commonly known as quicklime or burnt lime, is a widely used chemical compound. It is a white, Caustic (substance), caustic, alkaline, crystalline solid at room temperature. The broadly used term "''lime (material), lime''" connotes calcium-containing inorganic materials, in which carbonates, oxides and hydroxides of calcium, silicon, magnesium, aluminium, and iron predominate. By contrast, ''quicklime'' specifically applies to the single chemical compound calcium oxide. Calcium oxide that survives processing without reacting in building products such as cement is called free lime. Quicklime is relatively inexpensive. Both it and a chemical derivative (calcium hydroxide, of which quicklime is the base anhydride) are important commodity chemicals. Preparation Calcium oxide is usually made by the thermal decomposition of materials, such as limestone or seashells, that contain calcium carbonate (CaCO3; mineral calcite) in a lime kiln. This is accomplished by hea ...
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Decarboxylation
Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is the first chemical step in photosynthesis, is called carboxylation, the addition of CO2 to a compound. Enzymes that catalyze decarboxylations are called decarboxylases or, the more formal term, carboxy-lyases (Enzyme Commission number, EC number 4.1.1). In organic chemistry The term "decarboxylation" usually means replacement of a carboxyl group () with a hydrogen atom: :RCO2H -> RH + CO2 Decarboxylation is one of the oldest known organic reactions. It is one of the processes assumed to accompany pyrolysis and destructive distillation. Metal salts, especially copper compounds, facilitate the reaction via the intermediacy of metal carboxylate complexes. Decarboxylation of aryl carboxylates can generate the equivalent of the correspond ...
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