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|Section2= |Section3= |Section4= }} 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, which in turn is the backbone of a large number of psychoactive chemicals including antitussives, analgesics, and dissociative drugs. ==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. : This process involves electrophilic aromatic substitution using a tethered cyclohexanol group using diphosphorus pentoxide, which closes the central ring onto an existing aromatic ring. Dehydrogenation using selenium makes converts the other rings into aromatic ones as well. 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 Syntheses, Coll. Vol. 4, p.757 (1963); Vol. 34, p.76 (1954) (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) (Link ).〕 * Electrophilic halogenation to 9-bromophenanthrene with bromine〔Organic Syntheses, Coll. Vol. 3, p.134 (1955); Vol. 28, p.19 (1948) (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) (Link ).〕 * Ozonolysis to diphenylaldehyde〔Organic Syntheses, Coll. Vol. 5, p.489 (1973); Vol. 41, p.41 (1961) (Link ).〕 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「phenanthrene」の詳細全文を読む スポンサード リンク
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