Description
p-Toluylenediamine is a hair dye associated with
contact dermatitis in hairdressers. Cross reactivity is
observed with PPD.
Chemical Properties
Colorless plates. Soluble in water, ethanol, ether, and hot benzene 2,5-Toluenediamine is used in hair and fur dyes.
Uses
2,5-Toluenediamine is used primarily in hair dye formulations
as one of the major oxidation dye precursors. It is
also used in the synthesis of saframine, a family of dyes used
as biological stain, and may be present in indelible ink,
antifreeze, and nail polish.
As may be expected from its use in hair dye formulations,
hairdressers and barbers may be exposed to 2,5-TDA.
Workers in the dye manufacturing industry may also be
exposed.
Definition
ChEBI: A diamine in which the two amino groups are substituted into toluene at the 2- and 5-positions.
Synthesis Reference(s)
Journal of the American Chemical Society, 102, p. 6182, 1980
DOI: 10.1021/ja00539a054
Flammability and Explosibility
Non flammable
Contact allergens
Toluene-2,5-diamine is a permanent hair dye involved
in contact dermatitis in hairdressers and consumers. It
does not cross-react with PPD, but cosensitization is
frequent.
Safety Profile
Poison by ingestion and
subcutaneous routes. A skin irritant.
Mutation data reported. Questionable
carcinogen. Has a toxic action upon the liver
and can cause fatty degeneration of that
organ. Its total effect upon the body seems
to take place three chfferent ways. It is toxic
to the central nervous system, producing
jaundice by action on the liver and spleen,
and anemia by destruction of the red blood
cells. This action is quite similar to that of
aniline, although by no means identical with
it. Its high boiling point and the fact that the
material is solid at room temperature make it
somewhat less hazardous than aniline,
particularly at ordinary working
temperatures. The literature contains a
reference to a permanent injury to an eye
due to the use of this material as an eyelash
dye. It is considered to be an irritating dye
material. When heated to decomposition it
emits toxic fumes of NOx. See also other
toluene diamine entries and AROMATIC
AMINES.
Carcinogenicity
The possible carcinogenicity of 2,5-TDA (as sulfate salt
[6369-59-1]) was tested by the National Cancer Institute in a
dietary feeding study. Groups of 50 male and female
F344 rats (600 or 2000 ppm) and B6C3F1 mice (600 or
1000 ppm) were given diets containing 2,5-TDA for 78
weeks and then observed for an additional period of
28–31 weeks for rats and 16–19 weeks for mice. The only
statistically significant increased incidence was in lung
tumors in high-dose female mice, but the evidence was
not convincing enough to be attributed to 2,5-TDA. Overall,
the compound was considered noncarcinogenic.
