Phenanthrenequinone

Phenanthrenequinone is an organic compound with the formula C14H8O2. It is a yellow solid that is soluble in organic solvents. Phenanthrenequinone is used as a dye and a photographic developer. It is derived from phenanthrene, a polycyclic aromatic hydrocarbon.

Structure and synthesis

Phenanthrenequinone is a quinone derivative of phenanthrene. It consists of a phenanthrene core with two carbonyl groups attached at the 9 and 10 positions. The molecule is planar, as is typical for quinones.

Phenanthrenequinone can be synthesized from phenanthrene by oxidation with chromic acid. The reaction proceeds via a diol intermediate, which is then dehydrated to give the quinone.

Properties and uses

Phenanthrenequinone is a yellow solid that is soluble in organic solvents. It has a strong absorption in the ultraviolet and visible regions of the electromagnetic spectrum, which makes it useful as a dye.

In addition to its use as a dye, phenanthrenequinone is also used as a photographic developer. It is particularly useful for this purpose because it can be used in both acidic and alkaline solutions.

Phenanthrenequinone is also used in the synthesis of other organic compounds. For example, it can be used as a starting material for the synthesis of anthraquinone derivatives, which are used in the production of dyes and pigments.

Safety

Like many quinones, phenanthrenequinone is a strong oxidizing agent. It can cause burns and eye damage, and it is harmful if swallowed or inhaled. Appropriate safety precautions should be taken when handling this compound.

See also

• Phenanthrene
• Quinone
• Organic chemistry