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2,4,6-Trinitrobenzoic acid

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Impact-resistant high explosive
2,4,6-Trinitrobenzoic acid
Names
IUPAC name 2,4,6-Trinitrobenzoic acid
Identifiers
CAS Number
3D model (JSmol)
Abbreviations TNBA
ChemSpider
ECHA InfoCard 100.004.509 Edit this at Wikidata
EC Number
  • 204-958-2
PubChem CID
UNII
UN number 0215
CompTox Dashboard (EPA)
InChI
  • 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)
SMILES
  • C1=C(C=C(C(=C1(=O))C(=O)O)(=O))(=O)
Properties
Chemical formula C7H3N3O8
Molar mass 257.114 g·mol
Appearance pale yellow
Melting point 228.7 °C (Decomposes)
Solubility in water Insoluble
Solubility Soluble in acetone, methanol, benzene, ethanol, ether
log P 0.23
Vapor pressure 7.23 10mm Hg
Henry's law
constant (kH) 		2.62 10atm cu m/mol
Acidity (pKa) 0.65
Structure
Crystal structure Orthorhombic or rhombohedral
Hazards
Occupational safety and health (OHS/OSH):
Main hazards explosive
GHS labelling:
Pictograms GHS01: Explosive
Signal word Danger
Hazard statements H201
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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 and with dichromate.

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

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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