Trinitroanisole

Trinitroanisole
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
ECHA InfoCard 100.149.212 Edit this at Wikidata
EC Number
  • 620-419-8
UNII
  • InChI=1S/C7H5N3O7/c1-17-4-2-5(8(11)12)7(10(15)16)6(3-4)9(13)14/h2-3H,1H3 checkY
    Key: ASSSGXFIMKSEIH-UHFFFAOYSA-N checkY
  • COc1cc(c(c(c1)N(=O)=O)N(=O)=O)N(=O)=O
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
Occupational safety and health (OHS/OSH):
Main hazards
 explosive
GHS labelling:
GHS01: ExplosiveGHS07: Exclamation markGHS09: Environmental hazard
Danger
H201, H302, H312, H332, H411
P210, P230, P240, P250, P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P370+P380, 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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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]

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.

See also

Notes

  1. ^ a b Wasag-Chemie, Essen. "Explosivstoffe". 1961, p. 164.
  2. ^ PubChem. "2,4,6-Trinitroanisole". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-11-13.
  3. ^ Cahours, Auguste (1849). "Researches relatives à l'action du mélange d'acide sulfurique et d'acide nitrique fumants sur les matières organiques" [Investigations concerning the action of a mixture of sulfuric acid and fuming nitric acid on organic materials]. Annales de Chimie et de Physique. 3rd series (in French). 25: 5–44. See especially pp. 21-30.
  4. ^ Fedoroff, Basil T.; et al. (1960). Encyclopedia of Explosives and Related Items. Vol. 1. Dover, N.J.: Picatinny Arsenal. pp. A450–A453.