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
CAS Number	606-35-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	15546303 ;
ECHA InfoCard	100.149.212
EC Number	620-419-8;
PubChem CID	11817;
UNII	N042W5PE52;
CompTox Dashboard (EPA)	DTXSID6060551 ;
	InChI InChI=1S/C7H5N3O7/c1-17-4-2-5(8(11)12)7(10(15)16)6(3-4)9(13)14/h2-3H,1H3 Key: ASSSGXFIMKSEIH-UHFFFAOYSA-N ;
	SMILES COc1cc(c(c(c1)N(=O)=O)N(=O)=O)N(=O)=O;
Properties
Chemical formula	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
Solubility in water	insoluble in water, soluble in diethyl ether and hot ethanol
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	explosive
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H201, H302, H312, H332, H411
Precautionary statements	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). verify (what is ?) Infobox references

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.

Notes

^ ^a ^b Wasag-Chemie, Essen. "Explosivstoffe". 1961, p. 164.
^ PubChem. "2,4,6-Trinitroanisole". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-11-13.
^ 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.
^ Fedoroff, Basil T.; et al. (1960). Encyclopedia of Explosives and Related Items. Vol. 1. Dover, N.J.: Picatinny Arsenal. pp. A450–A453.

[Explosives-1] Wasag-Chemie, Essen. "Explosivstoffe". 1961, p. 164.

[:0-2] 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.

[1]

[2]

[3]

[4]

Synthesis

Use

See also

Notes