1,3,5-Trinitrobenzene Explained

1,3,5-Trinitrobenzene is one of three isomers of trinitrobenzene with the formula C₆H₃(NO₂)₃. A pale yellow solid, the compound is highly explosive.

Synthesis and reactions

1,3,5-Trinitrobenzene is produced by decarboxylation of 2,4,6-trinitrobenzoic acid.^[1]

1,3,5-Trinitrobenzene forms charge-transfer complexes with electron-rich arenes.

Reduction of 1,3,5-trinitrobenzene gives 1,3,5-triaminobenzene, a precursor to phloroglucinol.^[2]

Uses and applications

Trinitrobenzene is more explosive than TNT, but more expensive. It is primarily used as a high explosive compound for commercial mining and military applications. It has also been used as a narrow-range pH indicator, an agent to vulcanize natural rubber, and a mediating agent to mediate the synthesis of other explosive compounds.^[3]

See also

• 1,2,3-Trinitrobenzene
• TNT equivalent
• RE factor

Notes and References

1. 10.15227/orgsyn.002.0093. 1,3,5-Trinitrobenzene. Organic Syntheses. 1922. 2. 93. H. T.. Clarke. W. W.. Hartman.
2. 10.15227/orgsyn.009.0074. Phloroglucinol. Organic Syntheses. 1929. 9. 74. H. T.. Clarke. W. W.. Hartman.
3. Web site: John Pike . Explosives – Nitroaromatics . Globalsecurity.org . 1997-05-21 . 2013-10-28.