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Anthracene
Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes, as a scintillator to detect high energy particles, as production of pharmaceutical drugs. Anthracene is colorless but exhibits a blue (400–500 nm peak) fluorescence under ultraviolet radiation.
Crude anthracene (with a melting point of only 180°) was discovered in 1832 by Jean-Baptiste Dumas and Auguste Laurent who crystalized it from a fraction of coal tar later known as "anthracene oil". Since their (inaccurate) measurements showed the proportions of carbon and hydrogen of it to be the same as in naphthalene, Laurent called it paranaphtaline in his 1835 publication of the discovery, which is translated to English as paranaphthalene. Two years later, however, he decided to rename the compound to its modern name derived from Ancient Greek: ἄνθραξ, romanized: anthrax, lit. 'coal' because after discovering other polyaromatic hydrocarbons he decided it was only one of isomers of naphthalene. This notion was disproved in 1850s and 1860s.
Anthracene, as many other polycyclic aromatic hydrocarbons, is generated during combustion processes. Most human exposure is through tobacco smoke or ingestion of charred food.
The mineral form of anthracene is called freitalite and is related to a coal deposit. Coal tar, which contains around 1.5% anthracene, remains a major industrial source of this material. Common impurities are phenanthrene and carbazole.
A classic laboratory method for the preparation of anthracene is by cyclodehydration of o-methyl- or o-methylene-substituted diarylketones in the so-called Elbs reaction, for example from o-tolyl phenyl ketone.
Reduction of anthracene with alkali metals yields the deeply colored radical anion salts M+[anthracene]− (M = Li, Na, K). Reduction with sodium in ethanol gives 9,10-dihydroanthracene, preserving the aromaticity of the two flanking rings.
In any solvent except water, anthracene photodimerizes by the action of UV light:
The dimer, called dianthracene (or sometimes paranthracene), is connected by a pair of new carbon-carbon bonds, the result of the [4+4] cycloaddition. It reverts to anthracene thermally or with UV irradiation below 300 nm. Substituted anthracene derivatives behave similarly. The reaction is affected by the presence of oxygen.
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Anthracene
Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes, as a scintillator to detect high energy particles, as production of pharmaceutical drugs. Anthracene is colorless but exhibits a blue (400–500 nm peak) fluorescence under ultraviolet radiation.
Crude anthracene (with a melting point of only 180°) was discovered in 1832 by Jean-Baptiste Dumas and Auguste Laurent who crystalized it from a fraction of coal tar later known as "anthracene oil". Since their (inaccurate) measurements showed the proportions of carbon and hydrogen of it to be the same as in naphthalene, Laurent called it paranaphtaline in his 1835 publication of the discovery, which is translated to English as paranaphthalene. Two years later, however, he decided to rename the compound to its modern name derived from Ancient Greek: ἄνθραξ, romanized: anthrax, lit. 'coal' because after discovering other polyaromatic hydrocarbons he decided it was only one of isomers of naphthalene. This notion was disproved in 1850s and 1860s.
Anthracene, as many other polycyclic aromatic hydrocarbons, is generated during combustion processes. Most human exposure is through tobacco smoke or ingestion of charred food.
The mineral form of anthracene is called freitalite and is related to a coal deposit. Coal tar, which contains around 1.5% anthracene, remains a major industrial source of this material. Common impurities are phenanthrene and carbazole.
A classic laboratory method for the preparation of anthracene is by cyclodehydration of o-methyl- or o-methylene-substituted diarylketones in the so-called Elbs reaction, for example from o-tolyl phenyl ketone.
Reduction of anthracene with alkali metals yields the deeply colored radical anion salts M+[anthracene]− (M = Li, Na, K). Reduction with sodium in ethanol gives 9,10-dihydroanthracene, preserving the aromaticity of the two flanking rings.
In any solvent except water, anthracene photodimerizes by the action of UV light:
The dimer, called dianthracene (or sometimes paranthracene), is connected by a pair of new carbon-carbon bonds, the result of the [4+4] cycloaddition. It reverts to anthracene thermally or with UV irradiation below 300 nm. Substituted anthracene derivatives behave similarly. The reaction is affected by the presence of oxygen.