Anthracene

Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings.

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,[15] which is translated to English as paranaphthalene.

[14] Two years later, however, he decided to rename the compound to its modern name derived from Ancient Greek: ἄνθραξ, romanized: anthrax, lit.

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.

[21] In any solvent except water,[22] 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.

[23][24] Anthracene also reacts with dienophile singlet oxygen in a [4+2]-cycloaddition (Diels–Alder reaction): Chemical oxidation occurs readily, giving anthraquinone, C14H8O2 (below), for example using hydrogen peroxide and vanadyl acetylacetonate.

[28] Plastics, such as polyvinyltoluene, can be doped with anthracene to produce an approximately water-equivalent scintillator in radiation therapy dosimetry.

[30] Derivatives having a hydroxyl group are 1-hydroxyanthracene and 2-hydroxyanthracene, homologous to phenol and naphthols, and hydroxyanthracene (also called anthrol, and anthracenol)[31][32] are pharmacologically active.

Many investigations indicate that anthracene is noncarcinogenic: "consistently negative findings in numerous in vitro and in vivo genotoxicity tests".

Skeletal formula and numbering system of anthracene
Skeletal formula and numbering system of anthracene
Ball-and-stick model of the anthracene molecule
Anthracene
Anthracene
NFPA 704 four-colored diamond Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code
Diels alder reaction of anthracene with singlet oxygen
Diels alder reaction of anthracene with singlet oxygen
Anthraquione
Anthraquione
Fluorescence of anthracene under UV light
False-color AFM image of anthracene diradical, where hydrogen atoms are removed at carbons 9 and 10