Names | |
---|---|
Preferred IUPAC name 2,4,6-Trimethylpyridine | |
Identifiers | |
ECHA InfoCard | 100.003.286 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
Properties | |
C8H11N | |
Molar mass | 121.18 g·mol −1 |
Appearance | colourless liquid with pyridine-like smell [1] |
Melting point | -44,5 °C |
Boiling point | 171–172 °C [1] |
35 g·l−1 (20 °C) [1] | |
Vapor pressure | 4 hPa (20 °C) [1] |
Acidity (pKa) | 7.43 (25 °C) [2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
2,4,6-Trimethylpyridine (2,4,6-collidine) is an organic compound which belongs to the heterocycles (more precisely, heteroaromatics). It consists of a pyridine ring substituted with three methyl groups. It belongs to the substance group of the collidines, a group of six constitutional isomers. 2,4,6-trimethylpyridine is the most well-known isomer of this group.
The compound has a refractive index of 1.4959 (25 °C). [3]
2,4,6-Trimethylpyridine was isolated from Dippel's oil in 1854. [4] [5] A synthesis can be carried out analogously to the Hantzsch's dihydropyridine synthesis from ethyl acetoacetate (as β-ketocarbonyl compound), acetaldehyde and ammonia in the ratio 2: 1: 1. [6]
By oxidation of the methyl groups with potassium permanganate collidinic acid is obtained. [7]
2,4,6-Trimethylpyridine is used in organic syntheses (for example, for dehydrohalogenation [8] ), by binding the formed hydrogen halides.
Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one methine group (=CH−) replaced by a nitrogen atom (=N−). 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.
Acridine is an organic compound and a nitrogen heterocycle with the formula C13H9N. Acridines are substituted derivatives of the parent ring. It is a planar molecule that is structurally related to anthracene with one of the central CH groups replaced by nitrogen. Like the related molecules pyridine and quinoline, acridine is mildly basic. It is an almost colorless solid, which crystallizes in needles. There are few commercial applications of acridines; at one time acridine dyes were popular, but they are now relegated to niche applications, such as with acridine orange. The name is a reference to the acrid odour and acrid skin-irritating effect of the compound.
Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found in plants. Over 200 biologically active quinoline and quinazoline alkaloids are identified. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance.
Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula AlCl3. It forms a hexahydrate with the formula [Al(H2O)6]Cl3, containing six water molecules of hydration. Both the anhydrous form and the hexahydrate are colourless crystals, but samples are often contaminated with iron(III) chloride, giving them a yellow colour.
Caesium fluoride is an inorganic compound with the formula CsF. A hygroscopic white salt, caesium fluoride is used in the synthesis of organic compounds as a source of the fluoride anion. The compound is noteworthy from the pedagogical perspective as caesium also has the highest electropositivity of all commonly available elements and fluorine has the highest electronegativity.
Thionyl chloride is an inorganic compound with the chemical formula SOCl2. It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons.
In organic chemistry, the Knoevenagel condensation reaction is a type of chemical reaction named after German chemist Emil Knoevenagel. It is a modification of the aldol condensation.
Menthone is a chemical compound of the monoterpene class of naturally occurring organic compounds found in a number of essential oils, one that presents with minty flavor. It is a specific pair of stereoisomers of the four possible such isomers for the chemical structure, 2-isopropyl-5-methylcyclohexanone. Of those, the stereoisoomer l-menthone—formally, the (2S,5R)-trans isomer of that structure, as shown at right—is the most abundant in nature. Menthone is structurally related to menthol, which has a secondary alcohol (>C-OH) in place of the carbon-oxygen double bond projecting from the cyclohexane ring.
Collidine is the trivial name used to describe the chemical compounds which are trimethyl derivatives of pyridine. Their chemical properties resemble those of pyridine, although the presence of the methyl groups may prohibit some of the more straightforward reactions. Collidine comes in several isomers:
Pyrylium is a cation with formula C5H5O+, consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in the ring are conjugated as in benzene, giving it an aromatic character. In particular, because of the positive charge, the oxygen atom is trivalent. Pyrilium is a mono-cyclic and heterocyclic compound, one of the oxonium ions.
Neopentyl alcohol is a compound with formula (CH3)3CCH2OH. It is a colorless solid. The compound is one of the eight isomers of pentyl alcohol.
Picolinic acid is an organic compound with the formula NC5H4CO2H. It is a derivative of pyridine with a carboxylic acid (COOH) substituent at the 2-position. It is an isomer of nicotinic acid and isonicotinic acid, which have the carboxyl side chain at the 3- and 4-positions, respectively. It is a white solid although impure samples can appear tan. The compoundthat is soluble in water.
2,6-Lutidine is a natural heterocyclic aromatic organic compound with the formula (CH3)2C5H3N. It is one of several dimethyl-substituted derivative of pyridine, all of which are referred to as lutidines. It is a colorless liquid with mildly basic properties and a pungent, noxious odor.
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.
2,4,6-Trichlorophenol, also known as TCP, phenaclor, Dowicide 2S, Dowcide 2S, omal, is a chlorinated phenol that has been used as a fungicide, herbicide, insecticide, antiseptic, defoliant, and glue preservative. It is a clear to yellowish crystalline solid with a strong, phenolic odor. It decomposes on heating to produce toxic and corrosive fumes including hydrogen chloride and chlorine.
Arsabenzene (IUPAC name: arsinine) is an organoarsenic heterocyclic compound with the chemical formula C5H5As. It belongs to a group of compounds called heteroarenes that have the general formula C5H5E (E= N, P, As, Sb, Bi).
2-Methyl-1-butanol (IUPAC name, also called active amyl alcohol) is an organic compound with the formula CH3CH2CH(CH3)CH2OH. It is one of several isomers of amyl alcohol. This colorless liquid occurs naturally in trace amounts and has attracted some attention as a potential biofuel, exploiting its hydrophobic (gasoline-like) and branched structure. It is chiral.
The Kröhnke pyridine synthesis is reaction in organic synthesis between α-pyridinium methyl ketone salts and α, β-unsaturated carbonyl compounds used to generate highly functionalized pyridines. Pyridines occur widely in natural and synthetic products, so there is wide interest in routes for their synthesis. The method is named after Fritz Kröhnke.
Benzyl iodide is an organic compound with the chemical formula C
7H
7I. The compound consists of a benzene ring with an attached iodidemethyl group. The substance is an alkyl halide and is a constitutional isomer of the iodotoluenes.
Collidinic acid is an organic compound that belongs to the heterocycles. It belongs to the group of pyridinetricarboxylic acids and consists of a pyridine ring which carries three carboxy groups in the 2-, 4- and 6-positions. The name is derived from 2,4,6-collidine (2,4,6-trimethylpyridine).