Chemical Properties
This substance is an orange-red powder that can be dissolved in ethanol, acetone, and hydrochloric acid solution, but is not soluble in water.
Uses
4-Nitro-o-phenylenediamine was used to study the
in vitro activation of 4-nitro-o-phenylenediamine into a potent mutagen in
Salmonella typhimurium strain TA98 .
Production Methods
Commercial production of 4-nitro-o-PDA was first reported
in the United States in 1946. Two U.S. companies were
reported to produce undisclosed amounts of the chemical in
1975. U.S. imports of 4-nitro-o-PDA were reported to be
about 1900 kg in 1973 and 1100 kg in 1975. 4-Nitro-o-PDAis
used in fur dyes, inks, and semipermanent yellow hair
coloring formulations requiring a yellow color component
that does not involve the use of hydrogen peroxide in the
color development.
Occupational exposure to 4-nitro-o-PDA may occur
through inhalation and dermal contact with this compound
at workplaces where p-PDA is produced or used. The general
population may be exposed to the compound via dermal
contact, primarily through the use of hair dyes containing
this compound.
Definition
ChEBI: 4-nitro-1,2-phenylenediamine is the primary amino compound that is 1,2-phenylenediamine (o-phenylenediamine) substituted at the 4- (para-) position by a nitro group. It is a primary amino compound and a C-nitro compound. It is functionally related to a 1,2-phenylenediamine.
Application
4-Nitro-1,2-phenylenediamine is a hair dye constituent with potential mutagenic activity. It is used in oxidation hair dye formulations at a maximum concentration of 1.0 %, which after mixing typically in a 1:1 ratio with hydrogen peroxide just prior to use, corresponds to a concentration of 0.5% upon application.
Preparation
Prepared by reduction of 2,4-dinitroaniline using H2S in ammonia water.
General Description
4-nitro-o-phenylenediamine appears as dark red needles or red solid.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
4-Nitro-o-phenylenediamine is incompatible with strong oxidizing agents, strong acids, strong reducing agents, acid chlorides and acid anhydrides.
Fire Hazard
Flash point data for 4-Nitro-o-phenylenediamine are not available; however, 4-Nitro-o-phenylenediamine is probably combustible.
Biochem/physiol Actions
4-Nitro-o-phenylenediamine is a direct-acting mutagen.
Safety Profile
Moderately toxic by ingestion. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. Questionable carcinogen. When heated to decomposition it emits toxic fumes of NOx,.
Purification Methods
Crystallise the diamine from water. [Beilstein 13 IV 75.]
