Trinitroanisole

Synthesis

Trinitroanisole was first prepared in 1849 by the French chemist Auguste Cahours by reacting p-anisic acid (French: acide anisique) 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 (e.g., Japanese Type 91 or German Trinol), 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.

Notes

References

1. Wasag-Chemie, Essen. "Explosivstoffe". 1961, p. 164.
2. PubChem. "2,4,6-Trinitroanisole".
3. (1849). "Researches relatives à l'action du mélange d'acide sulfurique et d'acide nitrique fumants sur les matières organiques". Annales de Chimie et de Physique.
4. (1960). "Encyclopedia of Explosives and Related Items". Picatinny Arsenal.