Reactions of anthracene

Due to its less aromaticity than benzene, anthracene of reaction give both electrophilic substitution and addition reactions and these reactions occur at position 9 or 10 since the carbocations produced due to the attack of an electrophile on position 9 or 10 are the most stable since aromatic sextet is preserved in two of the three rings.

Electrophilic substitution reactions:



Nitration: Anthracene on nitration with aqueous nitric acid undergoes oxidation to form anthraquinone but with nitric acid in acetic acid at 15-20° C gives a mixture of 9-nitroanthracene and 9,10-dinitroanthracene


Friedel-Craft reaction: Friedel-Craft reaction occurs at 9- position in non-polar solvent but in presence of polar solvent it occurs at 1-position.

Friedel-Craft reaction

Sulphonation: Anthracene can be easily sulphonated to give a mixture of 1- and 2- sulphonic acids.

Reactions of anthracene

Formylation (Vilsmeier reaction): Anthracene can be formylated at 9-position when heated at 120 °C with N-methylformanilide in presence of POCl3.

Vilsmeier reaction

Addition reaction:

Diels-Alder reactions: Antharacene undergoes Diels-Alder reaction at 9- and 10- positions and forms endo-anthracene maleic anhydride.

Diels-Alder reactions

Reduction: When reduced with sodium and isopentanol, anthracene forms 9,10- dihydroanthracene. Catalytic reduction of anthracene using nickel at 200 – 250 °C makes tetra, hexa, octa, and finally perhydroanthracene (C14H24)


Oxidation: Anthracene on oxidation with potassium dichromate(K2Cr2O7) and sulphuric acid gives anthraquinone


Uses: Used as an insecticide for crops, wood preservative. Herbal drugs like senna, aloes, etc containing anthraquinones are used as laxatives/purgatives.

Make sure you also check our other amazing Article on : Resonance of Phenanthrene
Spread the love

Hello friends I’m Sameer Ray We tried our best to design this website in the way any pharmacy student would like and love to get. They can gather information and content about the pharmacy

Leave a Comment