1,3,5-Trinitrobenzene

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1,3,5-Trinitrobenzene [1]
Skeletal formula Trinitrobenzene.svg
Skeletal formula
Ball-and-stick model Trinitrobenzene-3D-balls.png
Ball-and-stick model
Names
Preferred IUPAC name
1,3,5-Trinitrobenzene
Other names
sym-Trinitrobenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.502 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
UN number 0388
  • C1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-]
Properties
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)
330 mg/L
−74.55·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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 [77 °F], 100 kPa).
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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]

Contents

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

References

  1. ↑ Record of 1,3,5-Trinitrobenzene in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 2 3 Booth, Gerald (2005). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN   978-3-527-30673-2.
  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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