Phenanthrene

Phenanthrene

Chembox new
ImageFile=Phenanthrene.pngImageSize=200px
IUPACName=Phenanthrene
OtherNames=
Section1= Chembox Identifiers
CASNo=85-01-8
PubChem=995
SMILES=c1ccc2c(c1)ccc3ccccc32
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
Formula=C14H10
MolarMass=178.23 g/mol
Appearance=
Density=
MeltingPt=
BoilingPt=
Solubility=
Section3= Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

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).

Chemistry

A classical phenanthrene synthesis is the "Bardhan-Sengupta Phenanthrene Synthesis" (1932). [chempensoftware.com [http://www.chempensoftware.com/reactions/RXN039.htm 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) [http://www.orgsynth.org/orgsyn/pdfs/CV4P0757.pdf 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) [http://www.orgsynth.org/orgsyn/pdfs/CV4P0313.pdf Link] .]
* Electrophilic halogenation to 9-bromophenanthrene with bromine [Organic Syntheses, Coll. Vol. 3, p.134 (1955); Vol. 28, p.19 (1948) [http://www.orgsynth.org/orgsyn/pdfs/CV3P0134.pdf 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) [http://www.orgsynth.org/orgsyn/pdfs/CV2P0482.pdf Link] .]
* Ozonolysis to diphenylaldehyde [Organic Syntheses, Coll. Vol. 5, p.489 (1973); Vol. 41, p.41 (1961) [http://www.orgsynth.org/orgsyn/pdfs/CV5P0489.pdf 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.

References

External links

* [http://www.scorecard.org/chemical-profiles/summary.tcl?edf_substance_id=85%2d01%2d8 Phenanthrene] at scorecard.org


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