https://www.sciencemadness.org/smwiki/index.php?title=Trinitrophloroglucinol&feed=atom&action=history
Trinitrophloroglucinol - Revision history
2024-03-28T10:23:06Z
Revision history for this page on the wiki
MediaWiki 1.25.1
https://www.sciencemadness.org/smwiki/index.php?title=Trinitrophloroglucinol&diff=13548&oldid=prev
Mabus at 19:47, 25 October 2020
2020-10-25T19:47:33Z
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<td colspan='2' style="background-color: white; color:black; text-align: center;">← Older revision</td>
<td colspan='2' style="background-color: white; color:black; text-align: center;">Revision as of 19:47, 25 October 2020</td>
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<tr><td class='diff-marker'> </td><td style="background-color: #f9f9f9; color: #333333; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #e6e6e6; vertical-align: top; white-space: pre-wrap;"><div>| BoilingPt_ref =  </div></td><td class='diff-marker'> </td><td style="background-color: #f9f9f9; color: #333333; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #e6e6e6; vertical-align: top; white-space: pre-wrap;"><div>| BoilingPt_ref =  </div></td></tr>
<tr><td class='diff-marker'> </td><td style="background-color: #f9f9f9; color: #333333; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #e6e6e6; vertical-align: top; white-space: pre-wrap;"><div>| BoilingPt_notes = Decomposes</div></td><td class='diff-marker'> </td><td style="background-color: #f9f9f9; color: #333333; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #e6e6e6; vertical-align: top; white-space: pre-wrap;"><div>| BoilingPt_notes = Decomposes</div></td></tr>
<tr><td class='diff-marker'>−</td><td style="color:black; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>| Density = 1.89 g/cm<sup>3</sup><ref>Wolff; Gredel; Irngartinger; Dreier; Acta Crystallographica, Section C: Crystal Structure Communications; vol. 52; nb. pt 12; (1996); p. 3225 - 3227</ref></div></td><td class='diff-marker'>+</td><td style="color:black; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>| Density = 1.89 g/cm<sup>3</sup><ref><ins class="diffchange diffchange-inline">[https://onlinelibrary.wiley.com/doi/epdf/10.1107/S0108270196009523 </ins>Wolff; Gredel; Irngartinger; Dreier; Acta Crystallographica, Section C: Crystal Structure Communications; vol. 52; nb. pt 12; (1996); p. 3225 - 3227<ins class="diffchange diffchange-inline">]</ins></ref></div></td></tr>
<tr><td class='diff-marker'> </td><td style="background-color: #f9f9f9; color: #333333; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #e6e6e6; vertical-align: top; white-space: pre-wrap;"><div>| Formula = C<sub>6</sub>H<sub>3</sub>N<sub>3</sub>O<sub>9</sub></div></td><td class='diff-marker'> </td><td style="background-color: #f9f9f9; color: #333333; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #e6e6e6; vertical-align: top; white-space: pre-wrap;"><div>| Formula = C<sub>6</sub>H<sub>3</sub>N<sub>3</sub>O<sub>9</sub></div></td></tr>
<tr><td class='diff-marker'> </td><td style="background-color: #f9f9f9; color: #333333; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #e6e6e6; vertical-align: top; white-space: pre-wrap;"><div>| HenryConstant =  </div></td><td class='diff-marker'> </td><td style="background-color: #f9f9f9; color: #333333; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #e6e6e6; vertical-align: top; white-space: pre-wrap;"><div>| HenryConstant =  </div></td></tr>
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Mabus
https://www.sciencemadness.org/smwiki/index.php?title=Trinitrophloroglucinol&diff=13547&oldid=prev
Mabus: Created page with "{{Chembox | Name = Trinitrophloroglucinol | Reference = | IUPACName = 2,4,6-Trinitrobenzene-1,3,5-triol | PIN = | SystematicName = | OtherNames = 1,3,5-Trihydroxy-2,4,6-trinit..."
2020-10-25T19:44:12Z
<p>Created page with "{{Chembox | Name = Trinitrophloroglucinol | Reference = | IUPACName = 2,4,6-Trinitrobenzene-1,3,5-triol | PIN = | SystematicName = | OtherNames = 1,3,5-Trihydroxy-2,4,6-trinit..."</p>
<p><b>New page</b></p><div>{{Chembox<br />
| Name = Trinitrophloroglucinol<br />
| Reference =<br />
| IUPACName = 2,4,6-Trinitrobenzene-1,3,5-triol<br />
| PIN =<br />
| SystematicName =<br />
| OtherNames = 1,3,5-Trihydroxy-2,4,6-trinitrobenzene<br>2,4,6-Trinitro-1,3,5-benzenetriol<br>2,4,6-Trinitro-1,3,5-trihydroxybenzene<br>2,4,6-Trinitro-1,3,5-trihydroxy-benzol<br>TNPG<br>Trinitro-phloroglucinol<br />
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| Appearance = Yellowish solid<br />
| BoilingPt = <br />
| BoilingPtC = <br />
| BoilingPt_ref = <br />
| BoilingPt_notes = Decomposes<br />
| Density = 1.89 g/cm<sup>3</sup><ref>Wolff; Gredel; Irngartinger; Dreier; Acta Crystallographica, Section C: Crystal Structure Communications; vol. 52; nb. pt 12; (1996); p. 3225 - 3227</ref><br />
| Formula = C<sub>6</sub>H<sub>3</sub>N<sub>3</sub>O<sub>9</sub><br />
| HenryConstant = <br />
| LogP = <br />
| MolarMass = 261.105 g/mol<br />
| MeltingPt = <br />
| MeltingPtC = 167-168<br />
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| MeltingPt_notes = <ref>Cantillo, David; Damm, Markus; Dallinger, Doris; Bauser, Marcus; Berger, Markus; Kappe, C. Oliver; Organic<br />
Process Research and Development; vol. 18; nb. 11; (2014); p. 1360 - 1366</ref><br />
| Odor = Odorless<br />
| pKa = <br />
| pKb = <br />
| Solubility = Soluble<br />
| SolubleOther = Soluble in [[dimethylformamide]], [[ethanol]]<br />
| Solvent = <br />
| VaporPressure = ~0 mmHg<br />
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'''Trinitrophloroglucinol''' ('''TNPG''') or '''2,4,6-trinitro-1,3,5-benzenetriol''' is a nitrated aromatic phenol, used as high explosive. It has the chemical formula '''C<sub>6</sub>H<sub>3</sub>N<sub>3</sub>O<sub>9</sub>'''.<br />
<br />
==Properties==<br />
===Chemical===<br />
Addition of trinitrophloroglucinol to an aq. solution of [[iron(III) chloride|ferric chloride]] gives a blue-violet product.<br />
<br />
[[Potassium bicarbonate]] mixed with TNPG gives its tripotassium salt.<br />
<br />
===Physical===<br />
Trinitrophloroglucinol is a yellowish or yellow-orange solid. It is soluble in water and organic solvents.<br />
<br />
===Explosive===<br />
There is little available data about TNGU's explosive properties. Some sources indicate that it's somewhat sensitive.<br />
<br />
Potassium salts of TNPG have been found to be more stable than its parent compound.<ref>https://www.sciencedirect.com/science/article/abs/pii/S0304389407001161?via%3Dihub</ref><br />
<br />
==Availability==<br />
TNPG is not available to the public and when available it's more expensive than similar explosive compounds.<br />
<br />
==Preparation==<br />
Trinitrophloroglucinol can be prepared via complete nitration of [[phloroglucinol]]. The reaction temperature is maintained between 5-10 °C. Yield is given as 91%.<ref>Straessler, Nicholas A.; Synthetic Communications; vol. 40; nb. 17; (2010); p. 2513 - 2519</ref><ref>https://patents.google.com/patent/US7737308B1/en</ref><br />
<br />
Refluxing [[hexanitrobenzene]] with [[hydrofluoric acid]] at 90 °C for 2 hours will produce TNPG, with an yield of 40%.<ref>[https://pubs.acs.org/doi/10.1021/jo00198a001 Nielsen, Arnold T.; Chafin, Andrew P.; Christian, Stephen L.; Journal of Organic Chemistry; vol. 49; nb. 24; (1984); p. 4575 - 4580]</ref><br />
<br />
==Projects==<br />
*Make blasting caps<br />
*Make colored compounds<br />
<br />
==Handling==<br />
===Safety===<br />
Trinitrophloroglucinol is toxic and a powerful explosive. Handle it with care.<br />
<br />
===Storage===<br />
In closed containers.<br />
<br />
===Disposal===<br />
Should be carefully incinerated or neutralized with an oxidizing solution.<br />
<br />
==References==<br />
<references/><br />
===Relevant Sciencemadness threads===<br />
*[http://www.sciencemadness.org/talk/viewthread.php?tid=4457 Crystal growth and preparative details of nitrophenols (stypnic, picric acid)]<br />
*[https://www.sciencemadness.org/whisper/viewthread.php?tid=485 reduction of syphnic acid]<br />
<br />
[[Category:Chemical compounds]]<br />
[[Category:Organic compounds]]<br />
[[Category:Aromatic compounds]]<br />
[[Category:Nitro compounds]]<br />
[[Category:Nitroaromatics]]<br />
[[Category:Acids]]<br />
[[Category:Phenols]]<br />
[[Category:Materials unstable in basic solution]]<br />
[[Category:Energetic materials]]<br />
[[Category:High explosives]]<br />
[[Category:Secondary explosives]]<br />
[[Category:Dyes]]</div>
Mabus