|Jmol-3D images||Image 1|
|Molar mass||178.23 g mol−1|
101 °C, 374 K, 214 °F ()
332 °C, 605 K, 630 °F ()
|Solubility in water||1.6 mg/L|
|Flash point||171 °C (340 °F)|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings. The name phenanthrene is a composite of phenyl and anthracene. In its pure form, it is found in cigarette smoke and is a known irritant, photosensitizing skin to light. Phenanthrene appears as a white powder having blue fluorescence.
The compound with a phenanthrene skeleton and nitrogens at the 4 and 5 positions is known as phenanthroline.
Phenanthrene is the backbone of morphinan.
A classical phenanthrene synthesis is the Bardhan–Sengupta phenanthrene synthesis.
The first step is an electrophilic aromatic substitution reaction, which is allowed when the diphosphorous pentoxide makes the alcohol a better leaving group. However, no alkenes outside of the initial aromatic ring are created. In the second step of this reaction 9,10-dihydrophenanthrene is oxidized with elemental selenium. The aromatization of six-membered rings by selenium is not clearly understood, but it does produce H2Se.
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 reduction to[9,10-dihydrophenanthrene with hydrogen gas and raney nickel 
- Electrophilic halogenation to 9-bromophenanthrene with bromine 
- Aromatic sulfonation to 2 and 3-phenanthrenesulfonic acids with sulfuric acid 
- Ozonolysis to diphenylaldehyde 
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.
- Record of CAS RN 85-01-8 in the GESTIS Substance Database from the IFA
- chempensoftware.com Link
- Organic Syntheses, Coll. Vol. 4, p.757 (1963); Vol. 34, p.76 (1954) Link
- Organic Syntheses, Coll. Vol. 4, p.313 (1963); Vol. 34, p.31 (1954) Link.
- Organic Syntheses, Coll. Vol. 3, p.134 (1955); Vol. 28, p.19 (1948) Link.
- Organic Syntheses, Coll. Vol. 2, p.482 (1943); Vol. 16, p.63 (1936) Link.
- Organic Syntheses, Coll. Vol. 5, p.489 (1973); Vol. 41, p.41 (1961) Link.
- Ravatite Mineral Data
- Phenanthrene at scorecard.org