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| Names | |
|---|---|
| Preferred IUPAC name Phenanthrene | |
| Identifiers | |
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3D model (JSmol) | |
| 1905428 | |
| ChEBI | |
| ChemSpider |
|
| ECHA InfoCard | 100.001.437 |
| EC Number |
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| 28699 | |
| KEGG |
|
| MeSH | C031181 |
| UNII | |
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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] | |
| 0D | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Phenanthrene is apolycyclic aromatic hydrocarbon (PAH) with formula C14H10, consisting of three fusedbenzene 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 thephenacenes, rather than straight as in theacenes. The compounds with a phenanthrene skeleton but with nitrogen atoms in place of CH sites are known asphenanthrolines.
Phenanthrene was discovered incoal tar in 1872 independently byCarl Graebe (article manuscript received on November 1st[5]) as well as byWilhelm Rudolph Fittig and his doctoral studentEugen Ostermayer [de] (manuscript received on November 19th[6] but Ostermayer defended his dissertation in August[7]). Fittig and Ostermayer were able to determine the structure of the compound by oxidizing it first to acorresponding quinone and then todiphenic acid, and soon Graebe confirmed it by a synthesis fromstilbene.[8]
Prior to February 1873 Fittig sent a letter to Graebe where he proposed to name the hydrocarbon phenanthrene (German:Phenanthren) in order to account for its similarity tobiphenyl andanthracene, which was swiftly adopted.[9]
Phenanthrene is nearly insoluble in water but is soluble in most low-polarity organic solvents such astoluene,carbon tetrachloride,ether,chloroform,acetic acid andbenzene.
Phenanthrene is fluorescent under ultraviolet light, exhibiting a largeStoke shift.[10] It can be used inscintillators.
Reactions of phenanthrene typically occur at the 9 and 10 positions, including:
Phenanthrene is extracted from coal tar, of which it comprises 5% by weight.[16]
In principle it could be obtained by chemical synthesis. TheBardhan–Sengupta phenanthrene synthesis is a classic way to make phenanthrenes.[17]
This process involveselectrophilic aromatic substitution using a tetheredcyclohexanol group usingdiphosphorus pentoxide, which closes the central ring onto an existing aromatic ring.Dehydrogenation usingseleniumaromatizes the other rings into aromatic ones as well. The aromatization of six-membered rings producesH2Se.
Phenanthrene can also be obtained photochemically from certaindiarylethenes (Mallory reaction):
Other synthesis routes include theHaworth reaction and theWagner-Meerwein-typering-expansion, as depicted below:
Commercially phenanthrene is not synthesized but extracted from the byproducts of coal coking, since it makes around 4–6% ofcoke oven coal tar.[18]
Morphinan is thechemical structure found in severalpsychoactive drugs, consisting ofopiateanalgesics,cough suppressants, anddissociativehallucinogens, among others. Examplesmorphine,codeine, anddextromethorphan (DXM).[16]
Ravatite is a natural mineral consisting of phenanthrene.[19] It is found in small amounts among a few coal burning sites. Ravatite represents a small group of organic minerals.
Phenanthrene derivatives occur in plants asphenanthrenoids. They have been reported from flowering plants, mainly in the familyOrchidaceae, and a few in the familiesDioscoreaceae,Combretaceae andBetulaceae, as well as in the lower plant classMarchantiophyta (liverworts).[20]
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