| Revision as of 16:19, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{chembox}} taken from revid 469904945 of page 1,3,5-Trinitrobenzene for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 02:47, 8 January 2024 edit Michael7604 (talk | contribs)Extended confirmed users8,895 edits it is an isomer of trinitrobenzene |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 446463348 |
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| verifiedrevid = 477204777 |
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| Reference = <ref>{{GESTIS|ZVG=38290|Name=1,3,5-Trinitrobenzene}}</ref> |
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| Reference = <ref>{{GESTIS|ZVG=38290|Name=1,3,5-Trinitrobenzene}}</ref> |
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| ImageFile = Trinitrobenzene.svg |
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| ImageFile = Trinitrobenzene.svg |
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| ImageSize1 = 160px |
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| ImageSize1 = 160px |
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| ImageName1 = Ball-and-stick model |
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| ImageName1 = Ball-and-stick model |
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| IUPACName = 1,3,5-Trinitrobenzene |
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| PIN = 1,3,5-Trinitrobenzene |
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| OtherNames = ''sym''-Trinitrobenzene |
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| OtherNames = ''sym''-Trinitrobenzene |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7156 |
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| ChemSpiderID = 7156 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 99-35-4 |
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| CASNo = 99-35-4 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 2H75703R1X |
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| PubChem = 7434 |
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| PubChem = 7434 |
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| UNNumber = 0388 |
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| UNNumber = 0388 |
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| SMILES = C1=C(C=C(C=C1(=O))(=O))(=O) |
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| SMILES = C1=C(C=C(C=C1(=O))(=O))(=O) |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=6|H=3|N=3|O=6 |
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| C=6 | H=3 | N=3 | O=6 |
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| Appearance = |
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| Appearance = |
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| Density = 1.76 g/cm<sup>3</sup> |
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| Density = 1.76 g/cm{{sup|3}} |
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| MeltingPtC = 123.2 |
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| MeltingPtC = 123.2 |
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| BoilingPtC = 315 |
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| BoilingPtC = 315 |
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| Solubility = 330 mg/L |
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| Solubility = 330 mg/L |
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| MagSus = -74.55·10{{sup|−6}} cm{{sup|3}}/mol |
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}} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| NFPA-F = 4 | NFPA-H = 2 | NFPA-R = 4 | NFPA-O = |
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| NFPA-F = 3 | NFPA-H = 2 | NFPA-R = 4 | NFPA-S = |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = }} |
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| AutoignitionPt = }} |
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}} |
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'''1,3,5-Trinitrobenzene''' is one of three isomers of ] with the formula C<sub>6</sub>H<sub>3</sub>(NO<sub>2</sub>)<sub>3</sub>. A pale yellow solid, the compound is highly explosive.<ref name=Ullmann>{{Ullmann |doi=10.1002/14356007.a17_411|title=Nitro Compounds, Aromatic|year=2005|last1=Booth|first1=Gerald}}</ref> |
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==Synthesis and reactions== |
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1,3,5-Trinitrobenzene is produced by ] of ].<ref name=Ullmann/><ref>{{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}}</ref> |
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1,3,5-Trinitrobenzene forms ]es with electron-rich arenes. |
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Reduction of 1,3,5-trinitrobenzene gives 1,3,5-triaminobenzene, a precursor to ].<ref>{{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}}</ref> |
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==Uses and applications== |
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Trinitrobenzene is more explosive than ], but more expensive.<ref name=Ullmann/> 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.<ref>{{cite web|author=John Pike |url=http://www.globalsecurity.org/military/systems/munitions/explosives-nitroaromatics.htm |title=Explosives – Nitroaromatics |publisher=Globalsecurity.org |date=1997-05-21 |accessdate=2013-10-28}}</ref> |
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==See also== |
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* ] |
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* ] |
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* ] |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Trinitrobenzene, 1, 3, 5-}} |
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] |
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] |