13-06603. Nitranilic Acid [Archived]

Nomenclature

CAS number: 479-22-1
2,5-Dihydroxy-3,6-dinitro-2,5-cyclohexadiene-1,4-dione; 2,5-dihydroxy-3,6-dinitro-p-benzoquinone; 2,5-dihydroxy-3,6-dinitroquinone.
C6H2N2O8; mol wt 230.09.
C 31.32%, H 0.88%, N 12.17%, O 55.63%.

Description and references

Prepd by treating hydroquinone diacetate with fuming nitric and concd sulfuric acids: Nietzki, Benckiser, Ber. 18, 499 (1885); Nietzki, Ber. 43, 3458 (1910); Meyer, Ber. 57, 326 (1924); Town, Biochem. J. 30, 1833 (1936).

Chemical structure

Properties

Solvated, golden-yellow plates from a little water + nitric acid. Effloresces at 100°, deflagrates at 170° without melting. Yellow prisms from ethyl acetate. Absorption max: 460 nm. Stable when kept away from moisture. Freely sol in water, alcohol. Insol in ether. Aq solns dec forming HCN and oxalic acid.

Status

This monograph has been retired and is no longer subject to revision or update.