2-Amino-5-nitrophenol

Brown to rust Crystalline powder

Reactant for:• ;Diazotation and coupling reactions1• ;Preparation of biologically and pharmacologically active molecules2

2-Amino-5-nitrophenol has been used as starting material in the synthesis of series of (Z)-2-(substituted aryl)-N-(3-oxo-4-(substituted carbamothioyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl) hydrazine carboxamides, as semi permanent (nonoxidative) hair colorant and as toner in permanent (oxidative) hair dye products, in synthesis of series of 7-benzylamino-2H-1,4-benzoxazin-3(4H)-ones, anticonvulsant agents. Also used as a reactant for, diazotation and coupling reactions, preparation of biologically and pharmacologically active molecules. It is also applied in hair dyes and to make azo dyes.

2-Amino-5-nitrophenol is used in hair dyes and as an intermediate in preparing azo dyes.

ChEBI: 2-Amino-5-nitrophenol is a member of 3-nitrophenols.

Brown amorphous granules or powder. Melting point 198-202°C.

Is slowly oxidized by air at room temperature. Insoluble in water.

2-Amino-5-nitrophenol is a reducing agent. Incompatible with strong oxidizing agents. Reacts slowly with oxygen in the air at room temperature. Stable at temperatures up to 140°F for two weeks when kept in the dark and under nitrogen. Stable under nitrogen for up to 24 weeks 77°F. Incompatible with strong bases . Incompatible with acid chlorides and acid anhydrides.

Flash point data for 2-Amino-5-nitrophenol are not available. 2-Amino-5-nitrophenol is probably combustible.

The potential carcinogenicity of 2-amino-5-nitrophenol was tested by NTP by oral administration (gavage) in corn oil to F344/N rats (100 and 200 mg/kg) and B6C3F1 mice (400 and 800 mg/kg) for 2 years. There was some evidence of carcinogenic activity in low-dose male rats, as indicated by increased incidence of acinar cell adenomas of the pancreas. No evidence of carcinogenic activity was found among female rats and the low-dose groups of male and female mice. The poor survival rates in the high-dose male rats and high-dose male and female mice reduced the sensitivity for detecting potential carcinogenic response.

Crystallise the phenol from water. [Beilstein 13 IV 803.]