Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Styphnic acid: Difference between pages

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470483322

| Name = Styphnic acid

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageFile = Styphnic_acid_structure01.svg

| ImageName = Styphnic acid

| 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}}

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 82-71-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = R4TJB1U00D

| SMILES = c1c(c(c(c(c1[N+](=O)[O-])O)[N+](=O)[O-])O)[N+](=O)[O-]

|Section2={{Chembox Properties

| Formula = C₆H₃N₃O₈

| MolarMass = 245.11 g/mol

| Density = 1.829 g/cm³

| MeltingPtC = 180

| BoilingPt = decomposes

}}

'''Styphnic acid''' (from [[Greek language|Greek]] ''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 [[astringent]] [[acid]] that forms hexagonal [[crystal]]s. It is used in the manufacture of [[dye]]s, [[pigment]]s, inks, medicines, and [[explosive]]s such as [[lead styphnate]]. It is itself a low-sensitivity explosive, similar to [[picric acid]], 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 [[Michel Eugène Chevreul]] 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 [[Pernambuco wood]] 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 [[Rudolf Christian Böttger]] 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==

It may be prepared by the nitration of [[resorcinol]] with a mixture of [[Nitric acid|nitric]] and [[sulfuric acid]].<ref name="powerlabs">{{cite web |last=Barros |first=Sam |title=PowerLabs Styphnic Acid Synthesis! |url=https://www.powerlabs.org/chemlabs/styphnic.htm |publisher=powerlabs.org |access-date=2015-05-20}}</ref>

This compound is an example of a [[Phenols|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==

<references/>

{{Authority control}}

[[Category:Nitrophenols]]

[[Category:Explosive chemicals]]

[[Category:Resorcinols]]

[[Category:Organic acids]]