254. Alizarine Orange

Nomenclature

CAS number: 568-93-4
1,2-Dihydroxy-3-nitro-9,10-anthracenedione; 1,2-dihydroxy-3-nitroanthraquinone; 3-nitroalizarin; C.I. Mordant Orange 14; C.I. 58015.
C14H7NO6; mol wt 285.21.
C 58.96%, H 2.47%, N 4.91%, O 33.66%.

Description and references

From 3-bromoalizarin in acetic acid with nitric acid: Barnett, Cook, J. Chem. Soc. 121, 1376 (1922). Additional prepns: Colour Index vol. 4 (3rd ed., 1971) p 4514.

Chemical structure

Properties

Orange needles or plates from acetic acid, dec 244°. Sublimes with partial decompn. Yellow in organic solvents, purple-red in dil aq alkali, orange in H2SO4.

Use

Dyes cloth mordanted with Al orange, with Fe red to violet. As indicator in satd alc soln. pH 2.0-4.0, color change from golden orange to flat yellow (in water). pH 5.0-6.5 from yellow to purplish red.