1,3,5-Trinitrobenzene

1,3,5-Trinitrobenzene[1]
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)
ChEBI
ChemSpider
ECHA InfoCard 100.002.502
EC Number
  • 202-752-7
Gmelin Reference
 27979
PubChem CID
UNII
UN number 0388
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H3N3O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H
    Key: UATJOMSPNYCXIX-UHFFFAOYSA-N
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
GHS labelling:[1]
Pictograms
 GHS01: ExplosiveGHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Signal word
 Danger
Hazard statements
 H201, H300, H310, H330, H373, H410
Precautionary statements
 P210, P230, P240, P250, P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P370+P380, P372, P373, P391, P401, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
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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Infobox references

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]

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

References

  1. ^ Record of 1,3,5-Trinitrobenzene in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ a b c 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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