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Styphnic acid

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Styphnic acid
Styphnic acid
Names
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
UN number 0219Dry or wetted with < 20% water/alcohol
0394Wetted 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
Boiling point dec.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

Styphnic acid, 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.

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, 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 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

  1. Synthesis of styphnic acid
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