1,3,5-Trinitrobenzene

1,3,5-Trinitrobenzene^[1]
Names
Skeletal formula Skeletal formula
Ball-and-stick model Ball-and-stick model
Preferred IUPAC name 1,3,5-Trinitrobenzene
Other names sym-Trinitrobenzene
Identifiers
CAS Number	99-35-4 ^checkY
3D model (JSmol)	Interactive image
ChemSpider	7156 ^checkY
ECHA InfoCard	100.002.502 Edit this at Wikidata
PubChem CID	7434
UNII	2H75703R1X ^checkY
UN number	0388
CompTox Dashboard (EPA)	DTXSID6021406 Edit this at Wikidata
SMILES C1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-]
Properties
Chemical formula	C₆H₃N₃O₆
Molar mass	213.105 g·mol⁻¹
Density	1.76 g/cm³
Melting point	123.2 °C (253.8 °F; 396.3 K)
Boiling point	315 °C (599 °F; 588 K)
Solubility in water	330 mg/L
Magnetic susceptibility (χ)	−74.55·10⁻⁶ cm³/mol
Hazards
NFPA 704 (fire diamond)	[画像:NFPA 704 four-colored diamond] Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline Instability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerin Special hazards (white): no code 2 3 4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). checkY verify (what is ^checkY☒N ?) Infobox references

Chemical compound

1,3,5-Trinitrobenzene is one of three isomers of trinitrobenzene with the formula C₆H₃(NO₂)₃. A pale yellow solid, the compound is highly explosive.^[2]

Synthesis and reactions

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1,3,5-Trinitrobenzene is produced by decarboxylation of 2,4,6-trinitrobenzoic acid.^[2]^[3]

1,3,5-Trinitrobenzene forms charge-transfer complexes with electron-rich arenes.

Reduction of 1,3,5-trinitrobenzene gives 1,3,5-triaminobenzene, a precursor to phloroglucinol.^[4]

Uses and applications

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Trinitrobenzene is more explosive than TNT, but more expensive.^[2] It is primarily used as a high explosive compound for commercial mining and military applications. It has also been used as a narrow-range pH indicator, an agent to vulcanize natural rubber, and a mediating agent to mediate the synthesis of other explosive compounds.^[5]

References

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^ Record of 1,3,5-Trinitrobenzene in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ ^a ^b ^c Booth, Gerald (2005). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3-527-30673-2.
^ 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.
^ John Pike (1997年05月21日). "Explosives – Nitroaromatics". Globalsecurity.org. Retrieved 2013年10月28日.

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Synthesis and reactions

Uses and applications

See also

References