Benzo(c)cinnoline

Benzo(c)cinnoline is a chemical compound that belongs to the class of organic compounds known as polycyclic aromatic hydrocarbons (PAHs). It is a heterocyclic compound with a structure based on a cinnoline skeleton with an additional benzene ring fused to it.

Structure and Properties

Benzo(c)cinnoline is a tricyclic compound that consists of a benzene ring fused to a cinnoline ring system. The cinnoline ring system is a bicyclic compound that consists of a six-membered ring fused to a five-membered ring, with two nitrogen atoms in the five-membered ring. The benzene ring is a six-membered ring consisting of six carbon atoms and six hydrogen atoms, with alternating single and double bonds.

The molecular formula of benzo(c)cinnoline is C13H8N2, and its molecular weight is 196.22 g/mol. It is a solid at room temperature, with a melting point of 208-210 °C.

Synthesis

The synthesis of benzo(c)cinnoline involves the condensation of aniline with malononitrile in the presence of sodium ethoxide, followed by cyclization and aromatization.

Applications

Benzo(c)cinnoline has potential applications in the field of organic electronics, due to its ability to form stable radicals and cations. It can also be used as a building block for the synthesis of more complex organic compounds.

Safety and Toxicity

As with other polycyclic aromatic hydrocarbons, benzo(c)cinnoline may have potential health risks. It is recommended to handle it with care and use appropriate safety measures.