2,4,6-Trinitrobenzoic acid

2,4,6-Trinitrobenzoic acid
Names
	IUPAC name 2,4,6-Trinitrobenzoic acid
Identifiers
CAS Number	129-66-8 ; 35860-50-5;
3D model (JSmol)	Interactive image;
Abbreviations	TNBA
ChemSpider	8204;
ECHA InfoCard	100.004.509
EC Number	204-958-2;
PubChem CID	8518;
UNII	134ID308V9;
UN number	0215
CompTox Dashboard (EPA)	DTXSID70861781 ;
	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[N+](=O)[O-])C(=O)O)[N+](=O)[O-])[N+](=O)[O-];
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:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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.

[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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