1,2-Naphthoquinone

1,2-naphthoquinone.svg

1,2-Naphthoquinone is an organic compound with the formula C₁₀H₆O₂. It is one of the two isomeric naphthoquinones, the other being 1,4-Naphthoquinone. This compound is a yellow solid that is slightly soluble in water.

Structure and Properties

1,2-Naphthoquinone consists of a naphthalene ring system with two carbonyl groups at the 1 and 2 positions. The presence of these carbonyl groups makes it a quinone, a class of compounds known for their role in redox reactions.

Synthesis

1,2-Naphthoquinone can be synthesized through the oxidation of 1,2-dihydroxynaphthalene using various oxidizing agents such as chromium trioxide or potassium permanganate.

Applications

1,2-Naphthoquinone is used in the synthesis of various dyes and pharmaceuticals. It also serves as an intermediate in the production of vitamin K analogs and other biologically active compounds.

Biological Activity

1,2-Naphthoquinone has been studied for its potential biological activities, including its role as an enzyme inhibitor and its effects on cell signaling pathways. It is known to generate reactive oxygen species (ROS), which can lead to oxidative stress in biological systems.

Safety and Handling

1,2-Naphthoquinone is classified as hazardous and should be handled with care. It can cause skin and eye irritation and may be harmful if inhaled or ingested. Proper personal protective equipment (PPE) such as gloves and goggles should be used when handling this compound.

See Also

• Naphthoquinone
• 1,4-Naphthoquinone
• Quinone
• Naphthalene