p-Acetotoluidide

p-Acetotoluidide Basic information
Product Name:p-Acetotoluidide
Synonyms:N-(4-METHYLPHENYL)ACETAMIDE;N-ACETYL-P-TOLUIDINE;N-P-TOLYLACETAMIDE;P-ACETOTOLUIDIDE;P-ACETOTOLUIDINE;P-TOLYLACETAMIDE;P-METHYLACETANILDE;4-(N-ACETYL)AMINOTOLUENE
CAS:103-89-9
MF:C9H11NO
MW:149.19
EINECS:203-155-4
Product Categories:Aromatics;Miscellaneous Reagents;Anilines, Amides & Amines;1
Mol File:103-89-9.mol
p-Acetotoluidide Structure
p-Acetotoluidide Chemical Properties
Melting point 149-151 °C(lit.)
Boiling point 307 °C(lit.)
density 1.21
vapor density 5.14
refractive index 1.5279 (estimate)
Fp 168 °C
storage temp. Store below +30°C.
solubility 1.2g/l (experimental)
form Crystals or Crystalline Powder
pka15.13±0.70(Predicted)
color Beige to light brown
Water Solubility 1 g/L (25 ºC)
Merck 14,74
BRN 607036
InChIKeyYICAMJWHIUMFDI-UHFFFAOYSA-N
CAS DataBase Reference103-89-9(CAS DataBase Reference)
NIST Chemistry ReferenceAcetamide, N-(4-methylphenyl)-(103-89-9)
EPA Substance Registry Systemp-Acetotoluidide (103-89-9)
Safety Information
Hazard Codes Xn
Risk Statements 22-36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS AN2930000
TSCA Yes
HS Code 29242995
ToxicityLD50 orl-rat: 2640 mg/kg MarJV# 29MAR77
MSDS Information
ProviderLanguage
4'-Methylacetanilide English
SigmaAldrich English
ACROS English
ALFA English
p-Acetotoluidide Usage And Synthesis
Descriptionp-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 PropertiesBEIGE TO LIGHT BROWN CRYSTALS OR CRYST. POWDER
Chemical Propertiesp-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).
Uses4′-Methylacetanilide was used in the synthesis of stable crystalline phosphorus ylides.
DefinitionChEBI: 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/ja01624a042
Organic Syntheses, Coll. Vol. 1, p. 111, 1941
Synthesis, p. 118, 1977
General DescriptionColorless needles.
Air & Water ReactionsWater insoluble.
Reactivity Profile4'-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 HazardACUTE/CHRONIC HAZARDS: When heated to decomposition 4'-Methylacetanilide emits toxic fumes.
Health HazardExposures 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 ProfileModerately 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
storagep-Acetanilide should be kept stored in a cool, dry place with the container closed when not in use
Purification MethodsCrystallise it from aqueous EtOH. [Beilstein 12 H 920, 12 I 420, 12 II 501, 12 III 2051, 12 IV 1902.]
PrecautionsDuring 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.
p-Acetotoluidide Preparation Products And Raw materials
Preparation Products4-Methyl-2-nitroaniline-->2-Bromo-4-methylaniline-->2'-BROMO-4'-METHYLACETANILIDE-->2,6-Dibromo-4-methylaniline-->3,4-DIBROMOTOLUENE-->4-BROMO-3-CHLOROTOLUENE-->3,5-dinitrotoluene-->toluene-3,5-diamine-->N-(4-Methylphenyl)ethanethioamide
Acetylspiramycin 4-ACETAMIDOBENZONITRILE 2-BENZOYLACETANILIDE 4-(3-Methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid ACETAMINOPHENOL BP/USP Bismaleimide N-METHYL-P-TOLUIDINE 3,3',5,5'-Tetramethylbenzidine dihydrochloride 2,4-DICHLORO-6-METHYLACETANILIDE,2,4-DICHLORO-6-METHYLACETANILIDE 2,3-DIMETHYL-1-(4-METHYLPHENYL)-3-PYRAZOLIN-5-ONE 2,2,2-TRICHLORO-3'-TRIFLUOROMETHYLACETANILIDE N1-(2,3-DICHLOROPHENYL)-2,2-DIMETHYLPROPANAMIDE 3'-Diethylamino-4'-methylacetanilide,3'-Diethylamino-4'-methylacetanilide 2'-Methyl-4'-chloro-5'-methylacetanilide,2'-Methyl-4'-chloro-5'-methylacetanilide o-Bromoacetanilidea 2-acetamido-3-nitro-9-fluorenone 4-CYANO-3-(TRIFLUOROMETHYL)ACETANILIDE p-Acetylamino benzoic acid

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