2,4,6-Trinitrobenzoic acid
{{Short description|Impact-resistant high explosive}}
{{Chembox
| ImageFile = Trinitrobenzoic acid.svg
| IUPACName = 2,4,6-Trinitrobenzoic acid
| Section1 = {{Chembox Identifiers
| Abbreviations = TNBA
| CASNo1 = 129-66-8
| CASNo1_Ref = {{Cascite|correct|CAS}}
| CASNo2 = 35860-50-5
| PubChem = 8518
| ChemSpiderID = 8204
| EC_number = 204-958-2
| UNNumber = 0215
| DrugBank =
| KEGG =
| MeSHName =
| ChEBI =
| RTECS =
| SMILES = C1=C(C=C(C(=C1[N+](=O)[O-])C(=O)O)[N+](=O)[O-])[N+](=O)[O-]
| 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)
| Beilstein =
| Gmelin =
| 3DMet =
| UNII = 134ID308V9
}}
| Section2 = {{Chembox Properties
| C = 7 | H =3 | N = 3 | O = 8
| Appearance = pale yellow
| Density =
| MeltingPt = 228.7 °C (Decomposes)
| BoilingPt =
| LogP = 0.23
| VaporPressure = 7.23 10−9mm Hg
| HenryConstant = 2.62 10−14atm cu m/mol
| pKa = 0.65
| pKb =
| Solubility = Insoluble
| SolubleOther = Soluble in acetone, methanol, benzene, ethanol, ether
}}
| Section3 = {{Chembox Structure
| CrystalStruct = Orthorhombic or rhombohedral
| Coordination =
| MolShape =
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| Section7 = {{Chembox Hazards
| MainHazards = explosive
| NFPA-H =
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| ExternalSDS =
| GHSPictograms = {{GHS01}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|201}}
| PPhrases = {{P-phrases|210|230|240|250|280|370+380|372|373|401|501}}
| FlashPt =
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| PEL =
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| Section8 = {{Chembox Related
| OtherCompounds =
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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{{Cite journal |last=Brown |first=D. J. |year=1947 |title=Improved preparation of 2:4:6-trinitrobenzoic acid |url=https://onlinelibrary.wiley.com/doi/10.1002/jctb.5000660510 |journal=Journal of the Society of Chemical Industry |language=en |volume=66 |issue=5 |pages=168 |doi=10.1002/jctb.5000660510}} and with dichromate.{{cite journal |doi=10.15227/orgsyn.002.0095|title=2,4,6-Trinitrobenzoic Acid|journal=Organic Syntheses|year=1922|volume=2|page=95|first1=H. T.|last1=Clarke|first2=W. W.|last2=Hartman}}
Upon heating, 2,4,6-trinitrobenzoic acid undergoes decarboxylation to give 1,3,5-trinitrobenzene.{{cite journal |doi=10.15227/orgsyn.002.0093|title=1,3,5-Trinitrobenzene|journal=Organic Syntheses|year=1922|volume=2|page=93|first1=H. T.|last1=Clarke|first2=W. W.|last2=Hartman}} Reduction with tin gives 2,4,6-triaminobenzenoic acid, a precursor to phloroglucinol (1,3,5-trihydroxybenzene).{{cite journal |doi=10.15227/orgsyn.009.0074|title=Phloroglucinol|journal=Organic Syntheses|year=1929|volume=9|page=74|first1=H. T.|last1=Clarke|first2=W. W.|last2=Hartman}}
References
{{DEFAULTSORT:Trinitrobenzoic acid, 2,4,6-}}