Styphnic acid

Styphnic acid
Identifiers
CAS number 82-71-3
PubChem 6721
ChemSpider 6465 Y
UN number 0219Dry or wetted with < 20% water/alcohol
0394Wetted with >= 20% water/alcohol
Jmol-3D images Image 1
Properties
Molecular formula C6H3N3O8
Molar mass 245.11 g/mol
Density 1.829 g/cm3
Melting point

180 °C

Boiling point

dec.

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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.[1]

Preparation and chemistry

It may be prepared by the nitration of resorcinol with a mixture of nitric and sulfuric acid.[2]

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. ^ [1]
  2. ^ Synthesis of styphnic acid