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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.
Oxidation of 1,10-phenanthroline with a mixture of nitric and sulfuric acids gives 1,10-phenanthroline-5,6-dione. [6] 1,10-Phenanthroline forms many coordination complexes. One example is the iron complex called ferroin. Alkyllithium reagents form deeply colored derivatives with phenanthroline.
It has been prepared by oxidation of phenanthrene with chromic acid. [3] It is used as an artificial mediator for electron acceptor/donor in Mo/W containing formate dehydrogenase reduction of carbon dioxide to formate and vice versa. It is a better electron acceptor than the natural nicotinamide adenine dinucleotide (NAD +).
1-Hydroxyphenanthrene is a phenanthrol and a human metabolite of phenanthrene that can be detected in urine of persons exposed to PAHs. [1]It can also be used as a marker for PAH pollution measured in marine fish bile.
ortho-Substituted substrates generally give 1-substituted phenanthrenes, unless the substituent is a good leaving group, in which case elimination to form unsubstituted phenanthrene occurs. [11] meta- Substituted substrates give mixtures of 2- and 4-substituted products. Substitution of the exocyclic double bond is well tolerated.
Phenanthrene can also be treated with other oxidizing agents (such as hydrogen peroxide, chromium trioxide, potassium dichromate, or potassium permanganate), which first yields phenanthrenequinone and gives diphenic acid on further oxidation.
Friedel–Crafts test for aromatic hydrocarbons [ edit ] Reaction of chloroform with aromatic compounds using an aluminium chloride catalyst gives triarylmethanes, which are often brightly colored, as is the case in triarylmethane dyes.
Nudol is a phenanthrene from the orchids Eulophia nuda, Eria carinata and Eria stricta. [10] 9,10-Dihydro-2,5-dimethoxyphenanthrene-1,7-diol is a phenanthrene from Eulophia nuda. This compound shows cytotoxic activity against human cancer cells. [11] 2,7-Dihydroxy-3,6-dimethoxyphenanthrene is a phenanthrene from Dehaasia longipedicellata. [12]