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Revision as of 15:35, 7 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.← Previous edit Latest revision as of 17:20, 4 August 2024 edit undoIra Leviton (talk | contribs)Extended confirmed users332,635 editsm Fixed references. Please see Category:CS1 errors: dates. 
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{{chembox {{chembox
| Verifiedfields = changed
⚫ | Name = Styphnic acid
| Watchedfields = changed
⚫ | ImageFile = Styphnic acid.png
| verifiedrevid = 470483322
⚫ <!-- | ImageSize = 150px -->
| ImageName = Styphnic acid | Name = Styphnic acid
| ImageFile_Ref = {{chemboximage|correct|??}}
⚫ | IUPACName = 2,4,6-trinitrobenzene-1,3-diol
| ImageFile = Styphnic_acid_structure01.svg
⚫ | Section1 = {{Chembox Identifiers
⚫ | ImageName = Styphnic acid
⚫ | ChemSpiderID = 6465
⚫ | ImageSize = 150px
| ImageFileL1 = Styphnic acid Ball and Stick.png
| ImageSizeL1 = 140px
⚫ | ImageFileR1 = Styphnic acid Space Fill.png
| ImageSizeR1 = 140px
⚫ | PIN = 2,4,6-Trinitrobenzene-1,3-diol
⚫ |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 6465
| PubChem = 6721 | PubChem = 6721
| InChI = 1/C6H3N3O8/c10-5-2(7(12)13)1-3(8(14)15)6(11)4(5)9(16)17/h1,10-11H | InChI = 1/C6H3N3O8/c10-5-2(7(12)13)1-3(8(14)15)6(11)4(5)9(16)17/h1,10-11H
| InChIKey = IXHMHWIBCIYOAZ-UHFFFAOYAQ | InChIKey = IXHMHWIBCIYOAZ-UHFFFAOYAQ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H3N3O8/c10-5-2(7(12)13)1-3(8(14)15)6(11)4(5)9(16)17/h1,10-11H | StdInChI = 1S/C6H3N3O8/c10-5-2(7(12)13)1-3(8(14)15)6(11)4(5)9(16)17/h1,10-11H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IXHMHWIBCIYOAZ-UHFFFAOYSA-N | StdInChIKey = IXHMHWIBCIYOAZ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 82-71-3 | CASNo = 82-71-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = R4TJB1U00D
| UNNumber = ] – ''Dry or wetted with < 20% water/alcohol''<br/>] – ''Wetted with >= 20% water/alcohol'' | UNNumber = ] – ''Dry or wetted with < 20% water/alcohol''<br/>] – ''Wetted with >= 20% water/alcohol''
| SMILES = c1c(c(c(c(c1(=O))O)(=O))O)(=O) | SMILES = c1c(c(c(c(c1(=O))O)(=O))O)(=O)
⚫ }}
⚫ |Section2={{Chembox Properties
⚫ | Formula = C<sub>6</sub>H<sub>3</sub>N<sub>3</sub>O<sub>8</sub>
⚫ | MolarMass = 245.11&nbsp;g/mol
⚫ | Density = 1.829&nbsp;g/cm<sup>3</sup>
| MeltingPtC = 180
⚫ | BoilingPt = decomposes
}} }}
⚫ | Section2 = {{Chembox Properties
⚫ | Formula = C<sub>6</sub>H<sub>3</sub>N<sub>3</sub>O<sub>8</sub>
⚫ | MolarMass = 245.11 g/mol
⚫ | Density = 1.829 g/cm<sup>3</sup>
| MeltingPt = 180 °C
⚫ | BoilingPt = dec.
⚫ }}
}} }}


'''Styphnic acid''', or 2,4,6-trinitro-1,3-benzenediol, is a yellow ] ] that forms hexagonal ]s. It is used in the manufacture of ]s, ]s, ]s, ]s, and ]s such as ]. It is itself a low sensitivity explosive, similar to ], but explodes upon rapid heating.<ref></ref> '''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>

== History ==
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>


==Preparation and chemistry== ==Preparation and chemistry==
⚫ 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>


⚫ This compound is an example of a ].
⚫ It may be prepared by the nitration of ] with a mixture of ] and ].<ref></ref>


⚫ Like picric acid, it is a moderately strong acid, capable of displacing carbon dioxide from solutions of ], for example.
⚫ This compound is an example of a trinitro].


⚫ It may be reacted with weakly basic oxides, such as those of lead and silver, to form the corresponding salts.
⚫ Like ], it is a moderately strong acid, displacing carbon dioxide from solutions of ] for example.


⚫ 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.
⚫ It may be reacted with weakly basic oxides such as those of lead and silver to form the corresponding salts.

⚫ The solubility of ] and styphnic acid in water is far less than the non nitrated phenol and less than the corresponding mono and di nitro compounds so they may be purified by fractional crystallisation.


==References== ==References==
<references/> <references/>


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