Styphnic acid

Styphnic acid
Names
	IUPAC name 2,4,6-trinitrobenzene-1,3-diol
Identifiers
CAS Number	82-71-3;
3D model (JSmol)	Interactive image;
ChemSpider	6465 ;
ECHA InfoCard	100.001.306
PubChem CID	6721;
UN number	0219 – Dry or wetted with < 20% water/alcohol; 0394 – Wetted with >= 20% water/alcohol
CompTox Dashboard (EPA)	DTXSID7058880 ;
	InChI InChI=1S/C6H3N3O8/c10-5-2(7(12)13)1-3(8(14)15)6(11)4(5)9(16)17/h1,10-11H Key: IXHMHWIBCIYOAZ-UHFFFAOYSA-N ; InChI=1/C6H3N3O8/c10-5-2(7(12)13)1-3(8(14)15)6(11)4(5)9(16)17/h1,10-11H Key: IXHMHWIBCIYOAZ-UHFFFAOYAQ;
	SMILES c1c(c(c(c(c1[N+](=O)[O-])O)[N+](=O)[O-])O)[N+](=O)[O-];
Properties
Chemical formula	C6H3N3O8
Molar mass	245.11 g/mol
Density	1.829 g/cm3
Melting point	180 °C
Boiling point	dec.
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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

[1]

[2]