Thianaphthene is an aromatic organic compound with a molecular formula C8H6S and an odor similar to naphthalene (mothballs). It occurs naturally as a constituent of petroleum-related deposits such as lignite tar.

Use

Thianaphthene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP. It is also used in the manufacturing of dyes such as thioindigo.

Thianaphthene may be used in the preparation of 2-thianapthenylphenyllithium, via metalation by n-butyllithium.

Synthesis

Most syntheses of benzothiophene create substituted benzothiophenes as a precursor to further reactions. An example is the reaction of an alkyne-substituted 2-bromobenzene with either sodium sulfide or potassium sulfide to form benzothiophene with an alkyl substitution at position 2.