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1,3,5-Trinitrobenzene

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1,3,5-Trinitrobenzene
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name 1,3,5-Trinitrobenzene
Other names sym-Trinitrobenzene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.502 Edit this at Wikidata
PubChem CID
UNII
UN number 0388
CompTox Dashboard (EPA)
SMILES
  • C1=C(C=C(C=C1(=O))(=O))(=O)
Properties
Chemical formula C6H3N3O6
Molar mass 213.105 g·mol
Density 1.76 g/cm
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 cm/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
2 3 4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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

Reduction of 1,3,5-trinitrobenzene gives 1,3,5-triaminobenzene, a precursor to phloroglucinol.

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.

See also

References

  1. Record of 1,3,5-Trinitrobenzene in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ Booth, Gerald (2005). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.
  3. Clarke, H. T.; Hartman, W. W. (1922). "1,3,5-Trinitrobenzene". Organic Syntheses. 2: 93. doi:10.15227/orgsyn.002.0093.
  4. Clarke, H. T.; Hartman, W. W. (1929). "Phloroglucinol". Organic Syntheses. 9: 74. doi:10.15227/orgsyn.009.0074.
  5. John Pike (1997-05-21). "Explosives – Nitroaromatics". Globalsecurity.org. Retrieved 2013-10-28.
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