2,4,6-Trinitrobenzoic acid
Impact-resistant high explosive
From Wikipedia, the free encyclopedia
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.
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| Names | |
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| IUPAC name
2,4,6-Trinitrobenzoic acid | |
| Identifiers | |
3D model (JSmol) |
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| Abbreviations | TNBA |
| ChemSpider | |
| ECHA InfoCard | 100.004.509 |
| EC Number |
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PubChem CID |
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| UNII | |
| UN number | 0215 |
CompTox Dashboard (EPA) |
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| 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 |
Henry's law constant (kH) |
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] | |
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| 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).
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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]