8859. Styphnic Acid

Nomenclature

CAS number: 82-71-3
2,4,6-Trinitro-1,3-benzenediol; 2,4,6-trinitroresorcinol; 2,4-dihydroxy-1,3,5-trinitrobenzene.
C6H3N3O8; mol wt 245.10.
C 29.40%, H 1.23%, N 17.14%, O 52.22%.

Description and references

May be prepd from natural sources, such as Pernambuco wood extract or quebracho extract by the action of nitric acid: Einbeck, Jablonski, Ber. 54, 1086 (1921). Prepd industrially by first sulfonating, then nitrating resorcinol: Merz, Zetter, Ber. 12, 681, 2037 (1879); Datta, Varma, J. Am. Chem. Soc. 41, 2043 (1919). Prepd by nitrating 2,4-dinitroresorcinol: Kametani, Ogasawara, Chem. Pharm. Bull. 15, 893 (1967).

Chemical structure

Properties

Hexagonal yellow crystals from dil alc. Astringent, but not bitter taste. Solvated crystals from acetic acid. Sublimes in high vacuum. Becomes almost colorless upon vacuum sublimation, but turns deep yellow on contact with air. When dry, mp 175.5°; also reported as mp 179-180°. One gram dissolves in 156 ml water at 14°, in 88 ml water at 62°. Freely sol in alcohol, ether. Acid to litmus. Dibasic acid. Deflagrates on rapid heating.

Use

Has been used in the manuf of explosives.