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Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) with formula C14H10, consisting of three fused benzene rings. It is a colorless, crystal-like solid, but can also appear yellow. Phenanthrene is used to make dyes, plastics, pesticides, explosives, and drugs. It has also been used to make bile acids, cholesterol and steroids.
Phenanthrene occurs naturally and also is a man-made chemical. Commonly, humans are exposed to phenanthrene through inhalation of cigarette smoke, but there are many routes of exposure. Animal studies have shown that phenanthrene is a potential carcinogen. However, according to IARC, it is not identified as a probable, possible or confirmed human carcinogen.
Phenanthrene's three fused rings are angled as in the , rather than straight as in the . The compounds with a phenanthrene skeleton but with nitrogen atoms in place of CH sites are known as .
Prior to February 1873 Fittig sent a letter to Graebe where he proposed to name the hydrocarbon phenanthrene () in order to account for its similarity to biphenyl and anthracene, which was swiftly adopted.
Phenanthrene is fluorescent under ultraviolet light, exhibiting a large Stokes shift. It can be used in Scintillator.
In principle it could be obtained by chemical synthesis. The Bardhan–Sengupta phenanthrene synthesis is a classic way to make phenanthrenes. (2025). 9780470638859 ISBN 9780470638859
This process involves electrophilic aromatic substitution using a tethered cyclohexanol group using diphosphorus pentoxide, which closes the central ring onto an existing aromatic ring. Dehydrogenation using selenium aromatizes the other rings into aromatic ones as well. The aromatization of six-membered rings produces H2Se.
Phenanthrene can also be obtained photochemically from certain (Mallory reaction):
Other synthesis routes include the Haworth reaction and the Wagner-Meerwein-type ring-expansion, as depicted below: phenanthrene is not synthesized but extracted from the byproducts of coal coking, since it makes around 4–6% of coke oven coal tar.
Ravatite is a natural mineral consisting of phenanthrene. Ravatite Mineral Data It is found in small amounts among a few coal burning sites. Ravatite represents a small group of organic minerals.
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