418. 1-Aminoanthraquinone-2-carboxylic Acid

Nomenclature

CAS number: 82-24-6
1-Amino-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid.
C15H9NO4; mol wt 267.24.
C 67.42%, H 3.39%, N 5.24%, O 23.95%.

Description and references

Prepd by reduction of 1-nitroanthraquinone-2-carboxylic acid with sodium sulfide: Terres, Ber. 46, 1639 (1913); by boiling 1-nitro-2-methylanthraquinone with alcoholic potassium hydroxide: Scholl, Monatsh. Chem. 34, 1011 (1913); by heating 1-nitro-2-bromomethylanthraquinone with sodium acetate and o-dichlorobenzene: Locher, Fierz, Helv. Chim. Acta 10, 667 (1927).

Chemical structure

Properties

Red needles from nitrobenzene, mp 295-296°. Soluble in aniline, boiling nitrobenzene, in sodium hydroxide and aq pyridine with formation of a deep red soln, in concd sulfuric acid with formation of a yellowish-brown soln; slightly sol in ether, benzene, alcohol. Insol in water, ligroin.

Derivative

Methyl ester.
C16H11NO4; mol wt 281.26.
C 68.33%, H 3.94%, N 4.98%, O 22.75%.

Properties

Red needles from glacial acetic acid, mp 228°.

Derivative

Ethyl ester.
C17H13NO4; mol wt 295.29.
C 69.15%, H 4.44%, N 4.74%, O 21.67%.

Properties

mp 198°.

Derivative

Phenyl ester.
C21H13NO4; mol wt 343.33.
C 73.46%, H 3.82%, N 4.08%, O 18.64%.

Properties

Reddish-golden crystals from glacial acetic acid, mp 198°.

Use

For the detection of traces of aluminum, magnesium, or zinc.