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 of matter, state from solid to liquid. At the melting point the solid and liquid phase (matter), phase exist in Thermodynamic equilib ...
of 68 °C. It is highly toxic. 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 ex ...
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 higher than the local speed of sound in t ...
of 7200 meters per
second
The second (symbol: s) is a unit of time derived from the division of the day first into 24 hours, then to 60 minutes, and finally to 60 seconds each (24 × 60 × 60 = 86400). The current and formal definition in the International System of U ...
.
[Wasag-Chemie, Essen. "Explosivstoffe". 1961, p. 164.] 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 Cahours by reacting
p-anisic acid (French: ''acide anisique'') with a mixture of
sulfuric acid
Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...
and
fuming nitric acid.
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 compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...
in the presence of
sodium hydroxide
Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions .
Sodium hydroxide is a highly corrosive base (chemistry), ...
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 Alcohol ...
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
A military, also known collectively as armed forces, is a heavily armed, highly organized force primarily intended for warfare. Militaries are typically authorized and maintained by a sovereign state, with their members identifiable by a d ...
explosive (e.g., Japanese or German ''Trinol''), having the advantage of being made from readily obtainable raw materials such as phenol
Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire.
The molecule consists of a phenyl group () ...
. However, due to its toxicity and 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 (''pikros''), meaning "bitter", due to its bitter taste. It is one of the most acidic phenols. Like ot ...
and dangerous picrate salts, its use has largely been abandoned.
See also
* 2,4-Dinitroanisole
Notes
{{reflist
Explosive chemicals
Nitrobenzene derivatives