1,3,5-Trinitrobenzene

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.^[2]

1,3,5-Trinitrobenzene^[1]

Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name 1,3,5-Trinitrobenzene
Other names sym-Trinitrobenzene
Identifiers
CAS Number	99-35-4 Y
3D model (JSmol)	Interactive image
ChemSpider	7156 Y
ECHA InfoCard	100.002.502
PubChem CID	7434
UNII	2H75703R1X Y
UN number	0388
CompTox Dashboard (EPA)	DTXSID6021406
SMILES C1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-]
Properties
Chemical formula	C6H3N3O6
Molar mass	213.105 g·mol−1
Density	1.76 g/cm3
Melting point	123.2 °C (253.8 °F; 396.3 K)
Boiling point	315 °C (599 °F; 588 K)
Solubility in water	330 mg/L
Magnetic susceptibility (χ)	−74.55·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)	2 3 4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Synthesis and reactions

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

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.^[4]

Uses and applications

Trinitrobenzene is more explosive than TNT, but more expensive.^[2] 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.^[5]

See also

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