It appears as colourless monoclinic crystals with a faint aromatic odour. Its solution exhibits blue fluorescence. It is composed of phenyl and anthracene, hence the name is phenanthrene. Anthracene is the linear isomer of phenanthrene.
![Structure of Phenanthrene](https://pharmacyscope.com/wp-content/uploads/2022/08/Screenshot-2022-08-18-182110.png)
It is used as an adhesive and sealant. Exposure to this compound may cause irritation to the skin and respiratory tract.
Phenanthrene undergoes additional reactions on the double bond between 9 and 10 which showed a strong olefinic character. The 9, 10-bond in phenanthrene closely resembles an alkene double bond in both its length and chemical reactivity. Hence, all chemical reactions of phenanthrene occur across 9, 10-bond.
Chemical Reaction of Phenanthrene
(1) Oxidation: Using, tert-butyl hydroperoxide and molybdenum acetylacetonate [MoO2 (acac)2] it can be oxidized to phenanthrenequinone.
![Reaction of Phenanthrene](https://pharmacyscope.com/wp-content/uploads/2022/08/Screenshot-2022-08-18-182223-1024x183.png)
(2) Reduction: When the solid lithium aluminium hydride is vigorously shaken with molten phenanthrene at high temperature, phenanthrene is reduced to 9, 10 dihydrophenanthrene.
![dihydrophenanthrene](https://pharmacyscope.com/wp-content/uploads/2022/08/Screenshot-2022-08-18-213323.png)
(3) Halogenation: Phenanthrene forms a crystalline dibromide which is sufficiently stable to be isolated. The dibromide can be converted further to mono Bromo product by gentle heating.
![Reaction of Phenanthrene](https://pharmacyscope.com/wp-content/uploads/2022/08/Screenshot-2022-08-18-213423-1024x203.png)
(4) Sulfonation: When phenanthrene is treated with conc. H2SO4, the following two products are obtained after neutralization with NaOH.
![phenanthrene](https://pharmacyscope.com/wp-content/uploads/2022/08/Screenshot-2022-08-18-213512-1024x480.png)
(5) Nitration: Upon treatment with a nitrating mixture, phenanthrene gives 9-nitro derivative.
![9-nitro derivative](https://pharmacyscope.com/wp-content/uploads/2022/08/Screenshot-2022-08-18-213644.png)
(6) Acylation: Phenanthrene undergoes acylation with acetyl chloride in the presence of aluminium chloride at 0°C to give 9-acetylphenanthrene acetyl.
![acetylphenanthrene](https://pharmacyscope.com/wp-content/uploads/2022/08/Screenshot-2022-08-18-213739-1024x230.png)
(7) Ozonolysis: Phenanthrene reacts quickly with one mole of ozone at the 9, 10-double bond to give mono ozonide derivative which upon further thermal decomposition, gives 2′-formyl-2-biphenyl carboxylic acid.
![Reaction of Phenanthrene](https://pharmacyscope.com/wp-content/uploads/2022/08/Screenshot-2022-08-18-213843-1024x204.png)
Synthesis of Phenanthrene:
(i) Friedel Craft’s acylation:
![Synthesis of Phenanthrene](https://pharmacyscope.com/wp-content/uploads/2022/08/Screenshot-2022-08-18-213934-1024x266.png)
(ii) Clemmensen reduction
![Synthesis of Phenanthrene](https://pharmacyscope.com/wp-content/uploads/2022/08/Screenshot-2022-08-18-214114-1024x257.png)
(iii) Ring closure
![Ring closure](https://pharmacyscope.com/wp-content/uploads/2022/08/Screenshot-2022-08-18-214300-1024x628.png)
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