Description
p-Acetotoluidide is an off-white to brown flake, odourless, solid or crystalline powder (pure
form), which is soluble in hot water, alcohol, ether, chloroform, acetone, glycerol, and benzene.
It is combustible and undergoes self-ignition (at 5450°C) but is otherwise stable under
most conditions. p-Acetanilide on decomposition releases carbon monoxide, oxides of nitrogen,
carbon dioxide, and toxic fumes. p-Acetanilide is used as an inhibitor of peroxides
and stabiliser for cellulose ester varnishes. It is used as an intermediate for the synthesis of
rubber accelerators, dyes and dye intermediate, and camphor. It is also used as a precursor
in penicillin synthesis and other pharmaceuticals including painkillers and intermediates.
Phenylacetamide structure shows analgesic and antipyretic effects. But acetanilide is not
used directly for this application due to causing methemoglobinemia (the presence of excessive
methemoglobin which does not function reversibly as an oxygen carrier in the blood).
Chemical Properties
BEIGE TO LIGHT BROWN CRYSTALS OR CRYST. POWDER
Chemical Properties
p-Acetotoluidide is an off-white to brown fl ake, odorless, solid or crystalline powder (pure
form), soluble in hot water alcohol, ether, chloroform, acetone, glycerol, and benzene. It
is combustible and undergoes self-ignition (at 545°C), but is otherwise stable under most
conditions. On decomposition, p-acetanilide releases carbon monoxide, oxides of nitrogen,
carbon dioxide, and toxic fumes. p-Acetanilide is used as an inhibitor of peroxides and a
stabilizer for cellulose ester varnishes. It is used as an intermediate for the synthesis of
rubber accelerators, dyes and dye intermediate, and camphor. It is also used as a precursor
in penicillin synthesis and other pharmaceuticals, including painkillers and intermediates.
Phenylacetamide structure shows analgesic and antipyretic effects. But acetanilide is
not used directly for this application because it causes methemoglobinemia (the presence
of excessive methemoglobin that does not function reversibly as an oxygen carrier in the
blood).
Uses
4′-Methylacetanilide was used in the synthesis of stable crystalline phosphorus ylides.
Definition
ChEBI: 4-acetamidotoluene is a member of the class of toluenes that is 4-aminotoluene in which one of the hydrogens attached to the amino group has been replaced by an acetyl group. It is a member of toluenes and a member of acetamides. It is functionally related to a p-toluidine.
Synthesis Reference(s)
Journal of the American Chemical Society, 77, p. 5092, 1955
DOI: 10.1021/ja01624a042Organic Syntheses, Coll. Vol. 1, p. 111, 1941
Synthesis, p. 118, 1977
General Description
Colorless needles.
Air & Water Reactions
Water insoluble.
Reactivity Profile
4'-Methylacetanilide is an amide. Flammable gases are formed by the reaction of organic amides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition 4'-Methylacetanilide emits toxic fumes.
Health Hazard
Exposures to p-acetotoluidide through ingestion or inhalation cause potential health
effects. The symptoms of toxicity include, but are not limited to, irritation to the eyes and
redness of the skin, wheezing, cough, shortness of breath, or burning in the mouth, throat,
or chest, and respiratory tract irritation.
Safety Profile
Moderately toxic by ingestion. See also ACETANILIDE. Combustible. When heated to decomposition it emits toxic fumes of NO,. To fight fire, use water, foam, CO2, dry chemical
storage
p-Acetanilide should be kept stored in a cool, dry place with the container closed when
not in use
Purification Methods
Crystallise it from aqueous EtOH. [Beilstein 12 H 920, 12 I 420, 12 II 501, 12 III 2051, 12 IV 1902.]
Precautions
During handling and use of p-aetotoluidide, proper personal protective equipment should
be worn. Avoid contact with the eyes, skin, and clothing. Avoid ingestion and inhalation.
On accidental exposure at the workplace, workers should immediately fl ush the eyes and
exposed part of the body with plenty of water. Workers should avoid using the contaminated
clothing and shoes.
