2,4,6-Trinitrobenzoic acid

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2,4,6-Trinitrobenzoic acid
Names
IUPAC name
2,4,6-Trinitrobenzoic acid
Identifiers
3D model (JSmol)
Abbreviations TNBA
ChemSpider
ECHA InfoCard 100.004.509 Edit this at Wikidata
EC Number
  • 204-958-2
UNII
UN number 0215
  • InChI=1S/C7H3N3O8/c11-7(12)6-4(9(15)16)1-3(8(13)14)2-5(6)10(17)18/h1-2H,(H,11,12)
  • C1=C(C=C(C(=C1[N+](=O)[O-])C(=O)O)[N+](=O)[O-])[N+](=O)[O-]
Properties
C7H3N3O8
Molar mass 257.114 g·mol−1
Appearance pale yellow
Melting point 228.7 °C (Decomposes)
Insoluble
Solubility Soluble in acetone, methanol, benzene, ethanol, ether
log P 0.23
Vapor pressure 7.23 10−9mm Hg
2.62 10−14atm cu m/mol
Acidity (pKa) 0.65
Structure
Orthorhombic or rhombohedral
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 explosive
GHS labelling:[1]
GHS01: Explosive
Danger
H201
P210, P230, P240, P250, P280, P370+P380, P372, P373, P401, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,4,6-Trinitrobenzoic acid (TNBA) is an organic compound with the formula (O2N)3C6H2CO2H. It is a high explosive nitrated derivative of benzoic acid.

Preparation and reactions

2,4,6-Trinitrobenzoic acid is prepared by oxidation of 2,4,6-trinitrotoluene (TNT). It is formed by oxidation of TNT and nitric acid with chlorate[2] and with dichromate.[3]

Upon heating, 2,4,6-trinitrobenzoic acid undergoes decarboxylation to give 1,3,5-trinitrobenzene.[4] Reduction with tin gives 2,4,6-triaminobenzenoic acid, a precursor to phloroglucinol (1,3,5-trihydroxybenzene).[5]

References

  1. ^ "2,4,6-Trinitrobenzoic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 1 April 2022.
  2. ^ Brown, D. J. (1947). "Improved preparation of 2:4:6-trinitrobenzoic acid". Journal of the Society of Chemical Industry. 66 (5): 168. doi:10.1002/jctb.5000660510.
  3. ^ Clarke, H. T.; Hartman, W. W. (1922). "2,4,6-Trinitrobenzoic Acid". Organic Syntheses. 2: 95. doi:10.15227/orgsyn.002.0095.
  4. ^ Clarke, H. T.; Hartman, W. W. (1922). "1,3,5-Trinitrobenzene". Organic Syntheses. 2: 93. doi:10.15227/orgsyn.002.0093.
  5. ^ Clarke, H. T.; Hartman, W. W. (1929). "Phloroglucinol". Organic Syntheses. 9: 74. doi:10.15227/orgsyn.009.0074.
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