Chemistry:Trinitroanisole

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Trinitroanisole
2,4,6-Trinitroanisole.svg
Names
Preferred IUPAC name
2-Methoxy-1,3,5-trinitrobenzene
Other names
2,4,6-Trinitroanisol; picric acid methyl esther; trisol; trinol; trinitroanisole
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 620-419-8
UNII
Properties
C7H5N3O7
Molar mass 243.131 g·mol−1
Appearance yellow, "leaf-like" crystals
Density 1.61 g/cm3
Melting point 68 °C (154 °F; 341 K)
Boiling point explodes
insoluble in water, soluble in diethyl ether and hot ethanol
Hazards
Main hazards explosive
GHS pictograms GHS01: ExplosiveGHS07: HarmfulGHS09: Environmental hazard
GHS Signal word Danger
H201, H302, H312, H332, H411
P210, P230, P240, P250, P261, P264, P270, P271, P273, P280, P301+312, P302+352, P304+312, P304+340, P312, P322, P330, P363, P370+380, P372, P373, P391, P401, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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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.[1] The compound's primary hazard is a blast of an instantaneous explosion, not flying projectiles or fragments.[2]

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.[3][4]

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.[1]

Molecular Formula

C7H5N3O7

Synonyms

  • 2-Methoxy-1,3,5-trinitrobenzene
  • Methyl picrate
  • 2,4,6-TRINITROANISOLE
  • 606-35-9
  • Ether, methyl picryl[2]

Use

Historically, trinitroanisole was used as a military explosive (e.g., Japanese Type 91), however, due to its tendency to form picric acid and dangerous picrate salts, its use has largely been abandoned.

Notes

  1. 1.0 1.1 Wasag-Chemie, Essen. "Explosivstoffe". 1961, p. 164.
  2. 2.0 2.1 PubChem. "2,4,6-Trinitroanisole" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/11817. 
  3. Cahours, Auguste (1849). "Researches relatives à l'action du mélange d'acide sulfurique et d'acide nitrique fumants sur les matières organiques" (in French). Annales de Chimie et de Physique. 3rd series 25: 5–44. https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dy4&view=1up&seq=11.  See especially pp. 21-30.
  4. Fedoroff, Basil T. (1960). Encyclopedia of Explosives and Related Items. 1. Dover, N.J.: Picatinny Arsenal. pp. A450–A453. https://archive.org/stream/Ullmans/01%20Ullmans-U-S-ARMY-Encyclopedia-of-Explosives-and-Related-Items-Vol-01#page/n557/mode/2up/.