9726. sym-Trinitrobenzene

Nomenclature

CAS number: 99-35-4
1,3,5-Trinitrobenzene; benzite.
C6H3N3O6; mol wt 213.10.
C 33.82%, H 1.42%, N 19.72%, O 45.05%.

Description and references

Prepared by decarboxylation of trinitrobenzoic acid, obtained by oxidation of TNT: Clarke, Hartman, Org. Synth. 2, 93 (1922); by the action of alkali on 2,4,6-trinitrobenzaldehyde: Secareanu, Bull. Soc. Chim. 51, 591 (1932). Use as explosive, less sensitive to impact than TNT but more powerful and brisant: Robertson, J. Chem. Soc. 119, 8 (1921); van Duin, Rec. Trav. Chim. 39, 687 (1920). Review of toxicology and human exposure: Toxicological Profile for 1,3-Dinitrobenzene and 1,3,5-Trinitrobenzene (PB95-264289, 1995) 168 p.

Chemical structure

Properties

Orthorhombic bipyramidal plates from glacial acetic acid. mp 122.5°. bp 315°. d420 1.76; d4152 1.4775. Log P (octanol:water) 1.18. Dimorphic, the other (rare) form melts at 61°. Can be sublimed by careful heating, explodes when heated rapidly. Absorption spectrum: Hatzsch, Picton, Ber. 42, 2121 (1909). Soly (g/100 g solvent): water 0.035; benzene 6.2; methanol 4.9; alcohol 1.9; ether 1.5; carbon disulfide 0.25; petr ether 0.05. Freely sol in dil Na2SO3 soln. LD50 orally in rats: 275 mg/kg (Toxicological Profile).

Use

Explosive. Vulcanizing agent for natural rubber. Indicator for pH 12.0-14.0.