Trinitroanisole is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

that exists as pale yellow crystals with a

melting point The melting point (or, rarely, liquefaction point) of a substance is the temperature at which it changes state from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium. The melting point of a substance depen ...

of 68 °C. It is an

explosive An explosive (or explosive material) is a reactive substance that contains a great amount of potential energy that can produce an explosion if released suddenly, usually accompanied by the production of light, heat, sound, and pressure. An expl ...

with a

detonation velocity Explosive velocity, also known as detonation velocity or velocity of detonation (VoD), is the velocity at which the shock wave front travels through a detonated explosive. Explosive velocities are always faster than the local speed of sound in t ...

of 7200 meters per

second The second (symbol: s) is the unit of time in the International System of Units (SI), historically defined as of a day – this factor derived from the division of the day first into 24 hours, then to 60 minutes and finally to 60 seconds ea ...

.Wasag-Chemie, Essen. "Explosivstoffe". 1961, p. 164.

Synthesis

Trinitroanisole was first prepared in 1849 by the French chemist Auguste Cahours by reacting

p-anisic acid ''p''-Anisic acid, also known as 4-methoxybenzoic acid or draconic acid, is one of the isomers of anisic acid. The term "anisic acid" often refers to this form specifically. It is a white crystalline solid which is insoluble in water, highly sol ...

(French: ''acide anisique'') with a mixture of

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular fo ...

and

fuming nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available nitric ...

. Trinitroanisole can be prepared by the reaction of 2,4-dinitrochlorobenzene with

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is ...

in the presence of

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and al ...

followed by the

nitration In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols an ...

of the resulting product. Alternatively, it can be prepared directly by the reaction of

picryl chloride Picryl chloride is an organic compound with the formula ClC6H2(NO2)3. It is a bright yellow solid that is highly explosive, as is typical for polynitro aromatics such as picric acid. Its detonation velocity is 7,200 m/s. Reactions The reactivit ...

with methanol in the presence of sodium hydroxide.

Use

Historically, trinitroanisole was used as a

military A military, also known collectively as armed forces, is a heavily armed, highly organized force primarily intended for warfare. It is typically authorized and maintained by a sovereign state, with its members identifiable by their distinct ...

explosive (e.g., Japanese '), however, due to its tendency to form

picric acid Picric acid is an organic compound with the formula (O2N)3C6H2OH. Its IUPAC name is 2,4,6-trinitrophenol (TNP). The name "picric" comes from el, πικρός (''pikros''), meaning "bitter", due to its bitter taste. It is one of the most acidic ...

and dangerous

picrate A picrate is a salt containing the anion (O2N)3C6H2O− or an ester derivative of the picrate anion. These salts are often produced by reactions of picric acid (2,4,6-trinitrophenol). The picrate ion is intensely yellow, although many of its salt ...

salts, its use has largely been abandoned.

Notes

{{reflist Explosive chemicals Nitrobenzenes