Phenanthridine

Phenanthridine is a polycyclic aromatic hydrocarbon that consists of three benzene rings connected by two carbon atoms. It is a basic structure of many natural and synthetic compounds. The name "phenanthridine" is derived from the three rings it contains: phenyl, anthracene, and pyridine.

Structure and Synthesis

Phenanthridine is a tricyclic compound, meaning it contains three rings. The rings are fused together, sharing two carbon atoms. The structure of phenanthridine is similar to that of anthracene, but with a nitrogen atom replacing one of the carbon atoms in the central ring.

Phenanthridine can be synthesized through several methods. One common method is the Bischler-Napieralski reaction, which involves the cyclization of a N-phenylethylamine derivative. Another method is the Pictet-Spengler reaction, which involves the condensation of a beta-phenylethylamine derivative with an aldehyde or ketone.

Properties and Uses

Phenanthridine is a colorless, crystalline solid. It is soluble in most organic solvents, but insoluble in water. It has a melting point of 101-102 degrees Celsius and a boiling point of 360 degrees Celsius.

Phenanthridine is used as a starting material in the synthesis of many natural and synthetic compounds. It is also used as a ligand in coordination chemistry.

Health Effects

Exposure to phenanthridine can cause irritation to the eyes, skin, and respiratory tract. Ingestion can cause nausea, vomiting, and abdominal pain. Long-term exposure can lead to liver and kidney damage.

See Also

• Polycyclic aromatic hydrocarbon
• Benzene
• Anthracene
• Pyridine
• Bischler-Napieralski reaction
• Pictet-Spengler reaction

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