Phenanthrene
| Phenanthrene | |
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Phenanthrene |
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| Identifiers | |
| CAS number | 85-01-8  |
| PubChem | 995 |
| UNII | 448J8E5BST |
| KEGG | C11422 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C14H10 |
| Molar mass | 178.23 g mol−1 |
| Appearance | Colorless solid |
| Density | 1.18 g/cm3[1] |
| Melting point |
101 °C, 374 K, 214 °F ([1]) |
| Boiling point |
332 °C, 605 K, 630 °F ([1]) |
| Solubility in water | 1.6 mg/L[1] |
| Hazards | |
| NFPA 704 |
 1
1
0
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| Flash point | 171 °C (340 °F)[1] |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
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.[citation needed] 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.
Contents |
[edit] Chemistry
Phenanthrene is nearly insoluble in water but is soluble in most organic solvents such as toluene, carbon tetrachloride, ether, chloroform, acetic acid and benzene.
A classical phenanthrene synthesis is the Bardhan-Sengupta phenanthrene synthesis.[2]
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 [3]
- Organic reduction to[9,10-dihydrophenanthrene with hydrogen gas and raney nickel [4]
- Electrophilic halogenation to 9-bromophenanthrene with bromine [5]
- Aromatic sulfonation to 2 and 3-phenanthrenesulfonic acids with sulfuric acid [6]
- Ozonolysis to diphenylaldehyde [7]
[edit] 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.
[edit] Natural occurrence
Ravatite is a natural analog of synthetic phenanthrene. It is found in small amounts among a few coal burning sites. Ravatite represents a small group of organic minerals.
[edit] References
- ^ a b c d e 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.
[edit] External links
- Phenanthrene at scorecard.org
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