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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 401065747
| Watchedfields = changed
⚫ | Name = Styphnic acid
⚫ | verifiedrevid = 470483322
⚫ | ImageFile = Styphnic acid.png
⚫ | Name = Styphnic acid
⚫ <!-- | ImageSize = 150px -->
| ImageFile_Ref = {{chemboximage|correct|??}}
⚫ | ImageName = Styphnic acid
| ImageFile = Styphnic_acid_structure01.svg
⚫ | IUPACName = 2,4,6-trinitrobenzene-1,3-diol
⚫ | ImageName = Styphnic acid
⚫ | Section1 = {{Chembox Identifiers
⚫ | ImageSize = 150px
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| 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 | ChemSpiderID = 6465
| PubChem = 6721 | PubChem = 6721
Line 16: Line 23:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | 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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Latest revision as of 17:20, 4 August 2024

Styphnic acid
Styphnic acid
Names
Preferred IUPAC name 2,4,6-Trinitrobenzene-1,3-diol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.306 Edit this at Wikidata
PubChem CID
UNII
UN number 0219 – Dry or wetted with < 20% water/alcohol
0394 – Wetted with >= 20% water/alcohol
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H3N3O8/c10-5-2(7(12)13)1-3(8(14)15)6(11)4(5)9(16)17/h1,10-11HKey: IXHMHWIBCIYOAZ-UHFFFAOYSA-N
  • InChI=1/C6H3N3O8/c10-5-2(7(12)13)1-3(8(14)15)6(11)4(5)9(16)17/h1,10-11HKey: IXHMHWIBCIYOAZ-UHFFFAOYAQ
SMILES
  • c1c(c(c(c(c1(=O))O)(=O))O)(=O)
Properties
Chemical formula C6H3N3O8
Molar mass 245.11 g/mol
Density 1.829 g/cm
Melting point 180 °C (356 °F; 453 K)
Boiling point decomposes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Styphnic acid (from Greek stryphnos "astringent"), or 2,4,6-trinitro-1,3-benzenediol, is a yellow astringent acid that forms hexagonal crystals. It is used in the manufacture of dyes, pigments, inks, medicines, and explosives such as lead styphnate. It is itself a low-sensitivity explosive, similar to picric acid, but explodes upon rapid heating.

History

It was discovered in 1808 by Michel Eugène Chevreul who was researching ways of producing colorants from tropical logwoods. Upon boiling Pernambuco wood extract with nitric acid he filtered crystals understood to be styphnic acid in an impure form. In mid-1840s chemists purified and systematically studied the substance with Rudolf Christian Böttger and Heinrich Will giving its modern name, while in 1871 J. Schreder proved that it's trinitroresorcinol.

Preparation and chemistry

It may be prepared by the nitration of resorcinol with a mixture of nitric and sulfuric acid.

This compound is an example of a trinitrophenol.

Like picric acid, it is a moderately strong acid, capable of displacing carbon dioxide from solutions of sodium carbonate, for example.

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

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.

References

  1. Alexander Senning (2006). Elsevier's Dictionary of Chemoetymology: The Whys and Whences of Chemical Nomenclature and Terminology, p. 375, at Google Books
  2. Armarego, W.L.F.; Chai, C.L.L. (2003). Purification of Laboratory Chemicals. Butterworth-Heinemann. p. 353. ISBN 9780750675710. Retrieved 2015-05-20.
  3. Annales de chimie (in French). Masson. 1808.
  4. Gmelin, Leopold (1848). Hand Book of Chemistry. Cavendish society.
  5. Böttger, Rudolph; Will, Heinrich (January 1846). "Ueber eine neue, der Pikrinsäure nahestehende Säure". Justus Liebigs Annalen der Chemie. 58 (3): 273–300. doi:10.1002/jlac.18460580302. ISSN 0075-4617.
  6. Schreder, J. (January 1871). "Ueber die Oxypikrinsäure (Styphninsäure)". Justus Liebigs Annalen der Chemie. 158 (2): 244–253. doi:10.1002/jlac.18711580207. ISSN 0075-4617.
  7. Roscoe, Henry Enfield (1887). The chemistry of the hydrocarbons and their derivatives, or Organic chemistry. 1882-1892. 6 v. D. Appleton.
  8. Barros, Sam. "PowerLabs Styphnic Acid Synthesis!". powerlabs.org. Retrieved 2015-05-20.
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