1-NITROANTHRAQUINONE

Chemical Properties

Yellow needles from AcOH;yellow plates by sublimation; soluble in EtOH and Et2O; slightly soluble in EtOAc, benzene and CHCl3; insoluble in water.

Uses

1-Nitroanthraquinone is used in the manufacture of various dyes, pharmaceuticals and similar products, either directly or after reduction to l-aminoanthraquinone.

Synthesis Reference(s)

Tetrahedron Letters, 16, p. 1429, 1975 DOI: 10.1016/S0040-4039(00)72160-5

Hazard

Hepatotoxic; moderately toxic; may cause hepatocellular neoplasms, subcutaneous fibromas, subcutaneous hemangiosarcomas, and type II pneumocyte proliferation.

Synthesis

1-Nitroanthraquinone is prepared by nitration of anthraquinone in nitric acid (danger of explosion!) , sulfuric acid , organic solvents , phosphoric acid , or hydrogen fluoride .
Purification from organic solvents by addition of bases, such as amines , alcoholates , or hydrazine , or from water by addition of sodium sulfite . 1-Nitroanthraquinone is crystallized from nitric acid , from organic solvents, for example, nitrobenzene , or from amides . The resulting 1-nitroanthraquinone may be finally purified by high-temperature distillation , .