Phenanthrene
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Preferred IUPAC name
Phenanthrene | |
Identifiers | |
3D model (
JSmol ) |
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1905428 | |
ChEBI | |
ChemSpider | |
ECHA InfoCard
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100.001.437 |
EC Number |
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28699 | |
KEGG | |
MeSH | C031181 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C14H10 | |
Molar mass | 178.234 g·mol−1 |
Appearance | Colorless solid |
Density | 1.18 g/cm3[1] |
Melting point | 101 °C (214 °F; 374 K)[1] |
Boiling point | 332 °C (630 °F; 605 K)[1] |
1.6 mg/L[1] | |
−127.9·10−6 cm3/mol | |
Hazards | |
NFPA 704 (fire diamond) | |
Flash point | 171 °C (340 °F; 444 K)[1] |
Structure | |
C2v[2] | |
0 D | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[3]
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.[3] However, according to IARC, it is not identified as a probable, possible or confirmed human carcinogen.[4]
Phenanthrene's three fused rings are angled as in the
Chemistry
Phenanthrene is nearly insoluble in water but is soluble in most low-polarity organic solvents such as toluene, carbon tetrachloride, ether, chloroform, acetic acid and benzene.
The Bardhan–Sengupta phenanthrene synthesis is a classic way to make phenanthrenes.[5]
This process involves
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[6]
- Electrophilic halogenation to 9-bromophenanthrene with bromine[8]
- Aromatic sulfonation to 2 and 3-phenanthrenesulfonic acids with sulfuric acid[9]
- Ozonolysis to diphenylaldehyde[10]
Canonical forms
Phenanthrene is more stable than its linear isomer
Natural occurrences
Ravatite is a natural mineral consisting of phenanthrene.[11] It is found in small amounts among a few coal burning sites. Ravatite represents a small group of organic minerals.
In plants
See also
References
- ^ a b c d e Record of CAS RN 85-01-8 in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ Peter Atkins, J. D. P., Atkins' Physical Chemistry. Oxford: 2010. P. 443.
- ^ a b "Phenanthrene Fact Sheet" (PDF). archive.epa.gov. U.S. Environmental Protection Agency. Retrieved 19 July 2019.
- ^ "Phenanthrene". Sigma-Alrdich.
- ISBN 9780470638859.
- ^ Organic Syntheses, Coll. Vol. 4, p. 757 (1963); Vol. 34, p. 76 (1954).
- ^ Organic Syntheses, Coll. Vol. 4, p. 313 (1963); Vol. 34, p. 31 (1954).
- ^ Organic Syntheses, Coll. Vol. 3, p. 134 (1955); Vol. 28, p. 19 (1948).
- ^ Organic Syntheses, Coll. Vol. 2, p. 482 (1943); Vol. 16, p. 63 (1936).
- ^ Organic Syntheses, Coll. Vol. 5, p. 489 (1973); Vol. 41, p. 41 (1961).
- ^ Ravatite Mineral Data
External links
- Phenanthrene at scorecard.org