1,3,5-Trinitrobenzene

1,3,5-Trinitrobenzene is an organic compound with the formula C6H3(NO2)3. It is one of three trinitrated benzene-derivatives. A pale yellow solid, the compound is highly explosive.[2]

1,3,5-Trinitrobenzene[1]
Names
IUPAC name
1,3,5-Trinitrobenzene
Other names
sym-Trinitrobenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.502
UNII
UN number 0388
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)
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
4
2
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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Infobox references

Explosive properties

1,3,5-Trinitrobenzene is a high explosive. It is moderately explosive in liquid form and extremely explosive in its dry powder form. It will detonate under strong shock. High temperatures, whether by sudden heating of any quantity, or by the accumulation of heat when large quantities are burning, will also cause detonation.

Synthesis and reactions

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

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 too expensive.[2] It used primarily as a high explosive for commercial mining and military use. Some other uses include a narrow-range pH indicator, an agent to vulcanize natural rubber, and a mediating agent to mediate the synthesis of other explosive compounds.[3]

Safety precautions

It is an extremely powerful oxidizing agent which may cause violent reaction with reducing materials.[4]

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.
  3. John Pike (1997-05-21). "Explosives – Nitroaromatics". Globalsecurity.org. Retrieved 2013-10-28.
  4. Sax, N. I. and Lewis, R. J. Sr. (1987) Hazardous chemicals desk reference. Van Nostrand Reinhold, New York. p. 664.
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