2-Fluoro-5-nitrobenzonitrile (CAS number 17417-09-3) is a benzene derivative with a fluorine, a nitrile and a nitro electron withdrawing groups. The triple-substituted 2-fluoro-5-nitrobenzonitrile is an ideal scaffold for molecular design. Each substituent has different reactivities, thus no protective group is required. Anti-tumour benzothiophene derivatives can be synthesized from 2-fluoro-5-nitrobenzonitrile reacting with methyl thioglycolate (93% yield). The synthetic route is fully customized and different functional groups can be introduced to the molecular scaffold depending on the desired lipophilicity and binding affinity. Other than benzothiophene, pyrroloquinoline and quinoline derivatives can be synthesized from 2-fluoro-5-nitrobenzonitrile.
The meta-position of nitro and nitrile groups allow 2-fluoro-5-nitrobenzonitrile to construct macrocycles.