| Revision as of 19:16, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 401067327 of page Styphnic_acid for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 17:20, 4 August 2024 edit Ira Leviton (talk | contribs)Extended confirmed users332,442 editsm Fixed references. Please see Category:CS1 errors: dates. |
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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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| verifiedrevid = 401065747 |
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| Name = Styphnic acid |
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| verifiedrevid = 470483322 |
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| ImageFile = Styphnic acid.png |
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| Name = Styphnic acid |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageName = Styphnic acid |
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| ImageFile = Styphnic_acid_structure01.svg |
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| IUPACName = 2,4,6-trinitrobenzene-1,3-diol |
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| ImageName = Styphnic acid |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ImageFileL1 = Styphnic acid Ball and Stick.png |
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| ImageSizeL1 = 140px |
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| ImageFileR1 = Styphnic acid Space Fill.png |
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| ImageSizeR1 = 140px |
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| PIN = 2,4,6-Trinitrobenzene-1,3-diol |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6465 |
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| ChemSpiderID = 6465 |
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| PubChem = 6721 |
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| PubChem = 6721 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = IXHMHWIBCIYOAZ-UHFFFAOYSA-N |
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| StdInChIKey = IXHMHWIBCIYOAZ-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 82-71-3 --> |
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| CASNo = 82-71-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = R4TJB1U00D |
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| UNNumber = ] – ''Dry or wetted with < 20% water/alcohol''<br/>] – ''Wetted with >= 20% water/alcohol'' |
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| UNNumber = ] – ''Dry or wetted with < 20% water/alcohol''<br/>] – ''Wetted with >= 20% water/alcohol'' |
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| SMILES = c1c(c(c(c(c1(=O))O)(=O))O)(=O) |
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| SMILES = c1c(c(c(c(c1(=O))O)(=O))O)(=O) |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>6</sub>H<sub>3</sub>N<sub>3</sub>O<sub>8</sub> |
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| Formula = C<sub>6</sub>H<sub>3</sub>N<sub>3</sub>O<sub>8</sub> |
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| MolarMass = 245.11 g/mol |
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| MolarMass = 245.11 g/mol |
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| Density = 1.829 g/cm<sup>3</sup> |
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| Density = 1.829 g/cm<sup>3</sup> |
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| MeltingPt = 180 °C |
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| MeltingPtC = 180 |
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| BoilingPt = dec. |
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| BoilingPt = decomposes |
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'''Styphnic acid''' (from ] ''stryphnos'' "astringent"<ref>Alexander Senning (2006). {{Google books|Fl4sdCYrq3cC|Elsevier's Dictionary of Chemoetymology: The Whys and Whences of Chemical Nomenclature and Terminology|page=375}}</ref>), or 2,4,6-trinitro-1,3-benzenediol, is a yellow ] ] that forms hexagonal ]s. It is used in the manufacture of ]s, ]s, inks, medicines, and ]s such as ]. It is itself a low-sensitivity explosive, similar to ], but explodes upon rapid heating.<ref name="google">{{cite book |last1=Armarego |first1=W.L.F. |last2=Chai |first2=C.L.L. |title=Purification of Laboratory Chemicals |url=https://books.google.com/books?id=SYzm1tx2z3QC |publisher=Butterworth-Heinemann |date=2003 |page=353 |access-date=2015-05-20 |isbn=9780750675710}}</ref> |
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== History == |
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It was discovered in 1808 by ] who was researching ways of producing colorants from tropical logwoods.<ref>{{Cite book |url=https://books.google.com/books?id=L3T_QPcDkX4C&pg=PA246 |title=Annales de chimie |date=1808 |publisher=Masson |language=fr}}</ref> Upon boiling ] extract with nitric acid he filtered crystals understood to be styphnic acid in an impure form.<ref>{{Cite book |last=Gmelin |first=Leopold |url=https://books.google.com/books?id=rfE4AAAAMAAJ&pg=PA228 |title=Hand Book of Chemistry |date=1848 |publisher=Cavendish society |language=en}}</ref> In mid-1840s chemists purified and systematically studied the substance with ] and Heinrich Will giving its modern name,<ref>{{Cite journal |last=Böttger |first=Rudolph |last2=Will |first2=Heinrich |date=January 1846 |title=Ueber eine neue, der Pikrinsäure nahestehende Säure |url=https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/jlac.18460580302 |journal=Justus Liebigs Annalen der Chemie |language=en |volume=58 |issue=3 |pages=273–300 |doi=10.1002/jlac.18460580302 |issn=0075-4617}}</ref> while in 1871 J. Schreder proved that it's trinitroresorcinol.<ref>{{Cite journal |last=Schreder |first=J. |date=January 1871 |title=Ueber die Oxypikrinsäure (Styphninsäure) |url=https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/jlac.18711580207 |journal=Justus Liebigs Annalen der Chemie |language=en |volume=158 |issue=2 |pages=244–253 |doi=10.1002/jlac.18711580207 |issn=0075-4617}}</ref><ref>{{Cite book |last=Roscoe |first=Henry Enfield |url=https://books.google.com/books?id=HnfN90Fi0XgC&pg=PA144 |title=The chemistry of the hydrocarbons and their derivatives, or Organic chemistry. 1882-1892. 6 v |date=1887 |publisher=D. Appleton |language=en}}</ref> |
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==Preparation and chemistry== |
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It may be prepared by the nitration of ] with a mixture of ] and ].<ref name="powerlabs">{{cite web |last=Barros |first=Sam |title=PowerLabs Styphnic Acid Synthesis! |url=http://www.powerlabs.org/chemlabs/styphnic.htm |publisher=powerlabs.org |access-date=2015-05-20}}</ref> |
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This compound is an example of a ]. |
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Like picric acid, it is a moderately strong acid, capable of displacing carbon dioxide from solutions of ], for example. |
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It may be reacted with weakly basic oxides, such as those of lead and silver, to form the corresponding salts. |
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The solubility of picric acid and styphnic acid in water is less than their corresponding mono- and di-nitro compounds, and far less than their non-nitrated precursor phenols, so they may be purified by fractional crystallisation. |
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==References== |
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<references/> |
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{{Authority control}} |
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