437. 2-Amino-4,6-dichlorophenol

Nomenclature

CAS number: 527-62-8
2,4-Dichloro-6-aminophenol; 4,6-dichloro-o-aminophenol.
C6H5Cl2NO; mol wt 178.02.
C 40.48%, H 2.83%, Cl 39.83%, N 7.87%, O 8.99%.

Description and references

Prepd by reduction of the corresponding nitrophenol: F. Fischer, Z. Chem. [N.F.] 4, 386 (1868); Ann. Suppl. 7, 189 (1870); Katz, Cohen, J. Org. Chem. 19, 758 (1954). Purification: J. Meyer, Helv. Chim. Acta 41, 1890 (1958).

Chemical structure

Properties

Long needles from carbon disulfide, warts from benzene, mp 95-96°. Sublimes (0.06 torr) 70-80° (bath temp). Freely sol in benzene, somewhat less in carbon disulfide, much less in petr ether. The stability of the free base (snow-white when pure) seems to be impaired by impurities.

Derivative

Hydrochloride.
C6H5Cl2NO.HCl; mol wt 214.48.
C 33.60%, H 2.82%, Cl 49.59%, N 6.53%, O 7.46%.

Properties

Crystals, dec 280-285°. Very stable when pure. The commercial product may be dark brown. Sol in water, alcohol. Precipitated from aq soln by the addition of concd HCl.

Use

Important azo-dye intermediate.