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Home > Encyclopedia > p-Aminoacetophenone

p-Aminoacetophenone

p-Aminoacetophenone structure

p-Aminoacetophenone 

structure
  • CAS No:

    99-92-3

  • Formula:

    C8H9NO

  • Chemical Name:

    p-Aminoacetophenone

  • Synonyms:

    Ethanone,1-(4-aminophenyl)-;Acetophenone,4′-amino-;Acetophenone,p-amino-;1-(4-Aminophenyl)ethanone;p-Aminoacetylbenzene;4-Acetylaniline;p-Acetylaniline;4′-Aminoacetophenone;1-Acetyl-4-aminobenzene;p-Aminophenyl methyl ketone;4-Aminophenyl methyl ketone;4-Acetylphenylamine;p-Aminoacetophenone;p-Acetylphenylamine;NSC 3242;T 3788;1-(4-Aminophenyl)ethan-1-one

  • Categories:

    Analytical Chemistry  >  Standard

Description

SLIGHTLY YELLOW TO BROWN CRYSTALLINE POWDER

p-Aminoacetophenone Basic Attributes

135.16300

135.16

202-801-2

1S58KH902I

3242

DTXSID6052669

Yellow monoclinic prisms from alcohol|Yellow needles

29223900

Characteristics

43.09000

0.8

Yellow To Brown Crystalline Powder

1.20 g/cm3

106 °C

293-295 °C

94.3ºC

1.571

In water, 3.35X10+3 mg/L at 37 deg C

Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from

4.32X10-4 mm Hg at 25 deg C (est)

LD50 orally in Rabbit: 381 mg/kg

Pleasant, characteristic odor

Henry's Law constant = 4.45X10-9 atm-cu m/mole at 25 °C (est)

pKa = 2.76 (conjugate acid)

Hydroxyl radical reaction rate constant = 1.05X10-10 cu cm/molec-sec at 25 °C (est)

Safety Information

NONH for all modes of transport

3

R22

S26; S36

AM5500000

Xn

Stable under normal temperatures and pressures.

P301 + P312 + P330

H302

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.|The following wastewater treatment technologies have been investigated for acetophenone: concentration process: activated carbon. /Acetophenone/|The following wastewater treatment technologies have been investigated for acetophone: concentration process: resin adsorption. /Acetophenone/

Milman HA, Peterson C; Apparent Correlation Between Structure and Carcinogenicity of Phenylenediamines and Related Cmpds; Environ Health Perspectives 56: 261-73 (1984).

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 137 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

4-Acetylaniline was detected in the effluent from a chemical manufacturing plant (sampling date in June 1973) in Newport, TN(1). The compound was detected not quantified in a raw sewage sample as part of an evaluation of the municipal sewage treatment systems in a treatment plant Harbin, China, May 2007(2).

Toxicity

LD50 RAT INTRAPERITONEAL 260 MG/KG

4-Acetylaniline's production and use as a laboratory reagent(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 25(SRC), determined from a log Kow of 0.83(2) and a regression-derived equation(3), indicates that 4-acetylaniline is expected to have very high mobility in soil(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4,5), suggesting that mobility may be much lower in some soils(SRC). Volatilization of 4-acetylaniline from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.4X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(6). 4-Acetylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.3X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(7). Aerobic biodegradation data were not available(SRC, 2011). No biodegradation was observed when incubated in digester sludge under anaerobic conditions for 8 weeks(8).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 25(SRC), determined from a log Kow of 0.83(2) and a regression-derived equation(3), indicates that 4-acetylaniline is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 4.4X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Aerobic biodegradation data were not available(SRC, 2011). No biodegradation was observed when incubated in digester sludge under anaerobic conditions for 8 weeks(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-acetylaniline, which has an estimated vapor pressure of 4.3X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 4-acetylaniline is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3.6 hours(SRC), calculated from its estimated rate constant of 1.05X10-10 cu cm/molecule-sec at 25 °C(3). Particulate-phase 4-acetylaniline may be removed from the air by wet or dry deposition(SRC). 4-Acetylaniline (in alcohol solution) has UV absorption maximum at 316 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 4-acetylaniline with photochemically produced hydroxyl radicals has been estimated to be 1.05X10-10 cu cm/molecule-sec at 25 °C(1) which corresponds to an atmospheric half-life of about 3.6 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(SRC). Aromatic amines and ketones are generally resistant to aqueous environmental hydrolysis(2); therefore, 4-acetylaniline is not expected to hydrolyze in water(SRC). As a class, aromatic amines react relatively rapidly in sunlit natural water via reaction with photochemically produced hydroxyl radicals and peroxy radicals(3); typical half-lives for hydroxyl radical and peroxy radical reaction are on the order of 19-30 sunlight hours(3); however, rate data specific to 4-acetylaniline were not located(SRC). 4-Acetylaniline (in alcohol solution) has UV absorption maximum at 316 nm(4) and therefore is may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for 4-acetylaniline(SRC), using a log Kow of 0.83(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of 4-acetylaniline is estimated as 25(SRC), using a log Kow of 0.83(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 4-acetylaniline is expected to have very high mobility in soil. However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4,5), suggesting that mobility may be much lower in some soils(SRC). The initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinoidal structures followed by oxidation of the product to give an amino-substituted quinone; these processes represent pathways by which aromatic amines may be converted to latent forms in the biosphere(6).

The Henry's Law constant for 4-acetylaniline is estimated as 4.4X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4-acetylaniline is expected to be essentially nonvolatile from water and moist soil surfaces(2). 4-Acetylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.3X10-4 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to 4-acetylaniline may occur through inhalation and dermal contact with this compound at workplaces where 4-acetylaniline is produced or used. (SRC)

Drug Information

P-AMINOACETOPHENONE IS KNOWN TO BE A POWERFUL METHEMOGLOBIN-FORMER IN VIVO.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aniline and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aniline and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aniline and related compounds/

4-aminoacetophenone

p-Aminoacetophenone Use and Manufacturing

Methods of Manufacturing

TRANSFER HYDROGENATION OF P-NITROACETOPHENONE WITH PALLADIUM CATALYST AND CYCLOHEXENE HYDROGEN DONOR

Uses

A novel utilization of aminophenone derivative in toxicology, for treating intoxications with cyanogenic toxic substances.

Ethanone, 1-(4-aminophenyl)-: ACTIVE

Computed Properties

Molecular Weight:135.16
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:135.068413911
Monoisotopic Mass:135.068413911
Topological Polar Surface Area:43.1
Heavy Atom Count:10
Complexity:125
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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