2,4,6-Trinitrobenzoic acid
Impact-resistant high explosive
Names | |
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IUPAC name 2,4,6-Trinitrobenzoic acid | |
Identifiers | |
CAS Number |
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3D model (JSmol) |
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Abbreviations | TNBA |
ChemSpider |
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ECHA InfoCard | 100.004.509 |
EC Number |
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PubChem CID |
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UNII |
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UN number | 0215 |
CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | C7H3N3O8 |
Molar mass | 257.114 g·mol−1 |
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 10−9mm Hg |
Henry's law constant (kH) | 2.62 10−14atm 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:[1] | |
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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 [77 °F], 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[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
- ^ "2,4,6-Trinitrobenzoic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 1 April 2022.
- ^ 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.
- ^ Clarke, H. T.; Hartman, W. W. (1922). "2,4,6-Trinitrobenzoic Acid". Organic Syntheses. 2: 95. doi:10.15227/orgsyn.002.0095.
- ^ Clarke, H. T.; Hartman, W. W. (1922). "1,3,5-Trinitrobenzene". Organic Syntheses. 2: 93. doi:10.15227/orgsyn.002.0093.
- ^ Clarke, H. T.; Hartman, W. W. (1929). "Phloroglucinol". Organic Syntheses. 9: 74. doi:10.15227/orgsyn.009.0074.