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Home > Encyclopedia > N-(4-Aminophenyl)acetamide

N-(4-Aminophenyl)acetamide

N-(4-Aminophenyl)acetamide structure

N-(4-Aminophenyl)acetamide 

structure
  • CAS No:

    122-80-5

  • Formula:

    C8H10N2O

  • Chemical Name:

    N-(4-Aminophenyl)acetamide

  • Synonyms:

    Acetamide,N-(4-aminophenyl)-;Acetanilide,4′-amino-;Acetanilide,p-amino-;N-(4-Aminophenyl)acetamide;C.I. 76005;p-Acetamidoaniline;Acetyl-p-phenylenediamine;C.I. Oxidation Base 19;Fourrine A;4′-Aminoacetanilide;Fourrine 88;p-Aminoacetanilide;N-Acetyl-p-phenylenediamine;4-(Acetylamino)aniline;4-Acetamidoaniline;N-(p-Aminophenyl)acetamide;1-Amino-4-(acetylamino)benzene;p-(Acetylamino)aniline;Acetparamin;p-Acetoaminoaniline;4-Acetoamidoaniline;N-Acetyl-1,4-benzenediamine;Paracetamin;N-Acetyl-1,4-phenylenediamine;(4-(Acetylamino)phenyl)amine;NSC 2135;4-Acetylaminobenzeneamine;4-Amino-N-acetylaniline;4-Amino-acetaniline

  • Categories:

    Dyes and Pigments  >  Dye

Description

PINK TO BROWN FINE CRYSTALLINE POWDERWhite or slightly reddish solid.


P-aminoacetanilide appears as white or slightly reddish solid. (NTP, 1992)


P-aminoacetanilide appears as white or slightly reddish solid. (NTP, 1992)

N-(4-Aminophenyl)acetamide Basic Attributes

150.18

150.18

742888

204-576-6

IH5OX0I3Z9

2135

DTXSID7024455

29242995

Characteristics

55.1

1.88140

Pink to brown Fine Crystalline Powder

1.19 g/cm3

166.5 °C

267 °C

195°C

1.6180 (estimate)

H2O: 0.1-1 g/100 mL at 25 ºC

Store below +30°C.

Oral-rat LD50: 3350 mg/kg

Open flame is flammable; heat releases toxic nitrogen oxide gas

Slightly soluble in water.

Amides and Imides

Aromatic amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Safety Information

IRRITANT

NONH for all modes of transport

1

36-42/43-20/21/22-R36

22-26-36/37-39-36-S39-S26

AD8225000

Xn,Xi

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

P261-P280-P305 + P351 + P338-P342 + P311

H317-H319-H334

Flash point data are not available for this chemical, but it is probably combustible. (NTP, 1992)

|Danger|H317 (80%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P264, P272, P280, P285, P302+P352, P304+P341, P305+P351+P338, P321, P333+P313, P337+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 73 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this compound should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should keep this material in a tightly-closed container under an inert atmosphere, and store it at refrigerated temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicity

moderately toxic

Drug Information

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and mucous membranes. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

4-aminoacetanilide

N-(4-Aminophenyl)acetamide Use and Manufacturing

Methods of Manufacturing

From dehydration water (acetanilide) through mixed acid nitrification to produce p-nitroacetanilide, and then reduced to p-aminoacetanilide with iron powder, the reaction solution is neutralized, crystallized and dried to get the finished product. 1. Nitrification Add 675kg of concentrated sulfuric acid (98%) in the kettle, stir, add 225kg of acetanilide (99%) at 20-25°C within 2-2.5h, and add it to make it completely soluble. Reduce the temperature to 7°C at 4-7°C, and add the mixed acid (made up of 63kg water, 60kg98% sulfuric acid and 107kg96% nitric acid) within about 20h. After dropwise addition, dilute in 4000L ice water and let stand for 1h. The upper layer of waste acid is siphoned off, the lower layer is filtered and washed with water until neutral to obtain p-nitroacetanilide. 2. Reduction: Add 700kg of water to the reduced wooden barrel, stir, add 110kg of iron powder and 4kg of acetic acid (98%), increase the temperature to 80℃, add the above half of the nitro compound to the 2-2.5kg, the temperature is controlled at 72-75℃ . After the addition, keep it for 1h and let it stand for 1h. The upper layer liquid is sucked into the neutralization kettle, and is neutralized with soda ash (about 4kg) to pH=8 at 70-75°C, and a small amount of sulfide alkali is added to remove iron ions. After standing for 1h, the supernatant liquid was sucked into the scraper-type crystallizing tank and cooled to 18°C. Centrifugal filtration and drying to obtain about 200kg of p-aminoacetanilide, the total yield is 80%. Producing p-aminoacetanilide can also start from p-nitroaniline, mix it with acetic acid and acetic anhydride, heat it for 4-5h, add water to filter out the crystals, wash and filter; then add the washed p-nitroacetanilide to water , Iron powder and acetic acid, heated and stirred for 4 hours, decolorized, filtered to remove iron oxide, the filtrate was cold precipitated crystals, filtered, and recrystallized with ethanol to obtain the finished product. Raw material consumption quota: acetanilide (98%) 1210kg/t, sulfuric acid (98%) 4000kg/t, nitric acid (95%) 577kg/t.

Uses

Intermediate in the manufacture of azo dyes, pharmaceuticals.

Acetamide, N-(4-aminophenyl)-: ACTIVE

Computed Properties

Molecular Weight:150.18
XLogP3:0.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:150.079312947
Monoisotopic Mass:150.079312947
Topological Polar Surface Area:55.1
Heavy Atom Count:11
Complexity:139
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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