Chembox new
Section1= Chembox Identifiers
InChI=1/C14H10/c1-3- 7-13-11(5-1)9-10- 12-6-2-4-8-14(12)13/ h1-10H

Section2= Chembox Properties
MolarMass=178.23 g/mol

Section3= Chembox Hazards

Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings. The name "phenanthrene" is a composite of phenyl and anthracene. It provides the framework for the Steroids. In its pure form, it is found in cigarette smoke and is a known irritant, photosensitising skin to light.

The compound with a phenanthrene skeleton and nitrogens at the 4 and 5 position is known as phenanthroline or 4,5-diazaphenanthrene (IUPAC name).


A classical phenanthrene synthesis is the "Bardhan-Sengupta Phenanthrene Synthesis" (1932). [ [ Link] ] In the second step of this reaction 9,10-dihydrophenanthrene is oxidized with elemental selenium. Phenanthrene can also be obtained photochemically from certain diarylethenes.

Reactions of phenanthrene typically occur at the 9 and 10 positions, including:
* Organic oxidation to phenanthrenequinone with chromic acid [Organic Syntheses, Coll. Vol. 4, p.757 (1963); Vol. 34, p.76 (1954) [ Link] ]
* Organic reduction to [9,10-dihydrophenanthrene with hydrogen gas and raney nickel [ Organic Syntheses, Coll. Vol. 4, p.313 (1963); Vol. 34, p.31 (1954) [ Link] .]
* Electrophilic halogenation to 9-bromophenanthrene with bromine [Organic Syntheses, Coll. Vol. 3, p.134 (1955); Vol. 28, p.19 (1948) [ Link] .]
* Aromatic sulfonation to 2 and 3-phenanthrenesulfonic acids with sulfuric acid [Organic Syntheses, Coll. Vol. 2, p.482 (1943); Vol. 16, p.63 (1936) [ Link] .]
* Ozonolysis to diphenylaldehyde [Organic Syntheses, Coll. Vol. 5, p.489 (1973); Vol. 41, p.41 (1961) [ Link] .]

Canonical forms

Phenanthrene is more stable than its linear isomer anthracene. A classic and well established explanation is based on Clar's rule. A novel theory invokes so-called stabilizing hydrogen-hydrogen bonds between the C4 and C5 hydrogen atoms.

Natural occurrence

Ravatite is a natural analogue of (synthetic) phenanthrene. It was found in little amounts among few burning coal sites. Ravatite represents a small group of organic minerals.


External links

* [ Phenanthrene] at

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Look at other dictionaries:

  • Phenanthrene — Phénanthrène Phénanthrène Structure du phénanthrène Général No CAS …   Wikipédia en Français

  • Phénanthrène — Structure du phénanthrène Général …   Wikipédia en Français

  • phénanthrène — [ fenɑ̃trɛn ] n. m. • 1890; de phénol et gr. anthrax « charbon » ♦ Chim. Carbure cyclique (C14H10) isomère de l anthracène, produit de la distillation du goudron de houille, utilisé pour fabriquer le noir de fumée et des matières colorantes. ●… …   Encyclopédie Universelle

  • Phenanthrene — Phe*nan threne, n. [Phenyl + antracene.] (Chem.) A complex hydrocarbon, {C14H10}, found in coal tar, and obtained as a white crystalline substance with a bluish fluorescence. [1913 Webster] …   The Collaborative International Dictionary of English

  • phenanthrene — [fə nan′thrēn΄] n. [< PHEN + ANTHR(AC)ENE] a colorless, crystalline hydrocarbon, C14H10, an isomer of the anthracene present in coal tar, used in making dyes, explosives, etc …   English World dictionary

  • phenanthrene — fenantrenas statusas T sritis chemija formulė C₁₄H₁₀ atitikmenys: angl. phenanthrene rus. фенантрен …   Chemijos terminų aiškinamasis žodynas

  • phenanthrene — noun Etymology: International Scientific Vocabulary phen + anthracene Date: 1882 a crystalline tricyclic aromatic hydrocarbon C14H10 of coal tar isomeric with anthracene …   New Collegiate Dictionary

  • phenanthrene — /feuh nan threen/, n. Chem. a colorless, shiny, crystalline, water insoluble isomer of anthracene, C14H10, derived from coal tar: used chiefly in dyestuffs and in the synthesis of drugs. [1880 85; PHEN + ANTHR + ENE] * * * …   Universalium

  • phenanthrene — noun A tricyclic aromatic hydrocarbon obtained from coal tar; used in the manufacture of dyes, pharmaceuticals and explosives; it is isomeric with anthracene …   Wiktionary

  • phenanthrene — A compound isomeric with anthracene, derived from coal tar; a major component of steroids, as cyclopenta[α]p.. Used as a basis for the synthesis of various dyes and drugs. * * * phen·an·threne fə nan .thrēn n a cry …   Medical dictionary

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