Trinitroanisole

Trinitroanisole

Names
IUPAC name 2-Methoxy-1,3,5-trinitrobenzene
Other names 2,4,6-Trinitroanisol; picric acid methyl ether; trisol; trinol; trinitroanisole
Identifiers
CAS Number	606-35-9 Y
3D model (Jmol)	Interactive image
ChemSpider	15546303 Y
ECHA InfoCard	100.149.212
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 Y Key: ASSSGXFIMKSEIH-UHFFFAOYSA-N Y
SMILES COc1cc(c(c(c1)N(=O)=O)N(=O)=O)N(=O)=O
Properties
Chemical formula	C7H5N3O7
Molar mass	243.13 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
Main hazards	explosive
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

Trinitroanisole is a chemical compound that exists as pale yellow crystals with a melting point of 68 °C. It is an explosive with a detonation velocity of 7200 meters per second.^[1]

Synthesis

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), however, due to its tendency to form picric acid and dangerous picrate salts, its use has largely been abandoned.

Notes