Trinitroanisole

Trinitroanisole is a chemical compound that exists as pale yellow crystals with a melting point of 68 °C. It is highly toxic. It is an explosive with a detonation velocity of 7200 meters per second. The compound's primary hazard is a blast of an instantaneous explosion, not flying projectiles or fragments.

Synthesis

Trinitroanisole was first prepared in 1849 by the French chemist Auguste [André Thomas Cahours|Auguste Cahours] by reacting p-anisic acid with a mixture of sulfuric acid and fuming nitric acid.
Trinitroanisole can be prepared by the reaction of 2,4-dinitrochlorobenzene with methanol in the presence of sodium hydroxide followed by the nitration of the resulting product. Alternatively, it can be prepared directly by the reaction of picryl chloride with methanol in the presence of sodium hydroxide.

Use

Historically, trinitroanisole was used as a military explosive, having the advantage of being made from readily obtainable raw materials such as phenol. However, due to its toxicity and tendency to form picric acid and dangerous picrate salts, its use has largely been abandoned.