p-Aminoacetophenone

HCID 7468

Basic information

CAS
99-92-3
Standard SMILES
CC(=O)c1ccc(N)cc1
InChIKey
GPRYKVSEZCQIHD-UHFFFAOYSA-N
Molecular formula
C8H9NO
Average molar mass
135.16 g/mol
Monoisotopic mass
135.06841391

Names & identifiers

Preferred name
p-Aminoacetophenone
IUPAC
1-(4-aminophenyl)ethanone
English name
4-Aminoacetophenone
Molecular formula
C8H9NO
Molecular weight
135.16

Names & synonyms

4'-Aminoacetophenone99-92-31-(4-Aminophenyl)ethanone4-Aminoacetophenonep-Aminoacetophenone4-ACETYLANILINEp-AcetylanilineEthanone, 1-(4-aminophenyl)-p-AminoacetylbenzeneAcetophenone, p-amino-USAF EK-631Acetophenone, 4-amino-
Show more names
Clenbuterol EP Impurity D1-(4-aminophenyl)-ethanonNSC 3242usafek-631
1S58KH902INSC-3242DTXSID6052669para-aminoacetophenoneRefChem:97827DTXCID7031242202-801-21-(4-Aminophenyl)Ethan-1-One

Database identifiers

CAS
99-92-3
PubChem CID
7468
DTXSID
DTXSID6052669
ChEMBL
CHEMBL3278329
UNII
1S58KH902I
EC Number
202-801-2
Nikkaji
J3.228J

Properties

Computed structural properties

XLogP
0.8
Topological polar surface area
43.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
10

Experimental & physicochemical properties

LogPlog Kow = 0.83
OdorPleasant, characteristic odor
Color/Form · 2 items

Yellow monoclinic prisms from alcohol

Yellow needles

Solubility · 3 items

Soluble in hydrochloric acid

Very soluble in ether and ethanol

In water, 3.35X10+3 mg/L at 37 °C

Boiling Point294 °C; 195 °C at 15 mm Hg
Melting Point106 °C

Physicochemical properties

Melting point
103 · 103-107 °C(lit.)
Boiling point
293 °C · 293 °C(lit.)
Density
0 · 0,77 g/cm
bulk density
580 kg/m3 · 580kg/m3
refractive index
1.57 · 1.5700 (estimate)
Flash point
292 · 292-294°C

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral];H312 (67.1%): Harmful in contact with skin [Warning Acute toxicity, dermal];H315 (30.3%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (30.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H332 (67.7%): Harmful if inhaled [Warning Acute toxicity, inhalation];H335 (29.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 155 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory InformationChemical: Ethanone, 1-(4-aminophenyl)-
Hazards Summary · 1 item

A strong inducer of methemoglobin in vivo; Emergency treatment: Aniline; [HSDB] Methemoglobinemia observed in oral lethal-dose study of dogs; [RTECS] An irritant; Toxic if swallowed; May be harmful by inhalation or skin absorption; [Aldrich MSDS] See Aniline.

Special ReportsMilman HA, Peterson C; Apparent Correlation Between Structure and Carcinogenicity of Phenylenediamines and Related Cmpds; Environ Health Perspectives 56: 261-73 (1984).
Hazard Classes and CategoriesAcute Tox. 4 (100%);Acute Tox. 4 (67.1%);Skin Irrit. 2 (30.3%);Eye Irrit. 2A (30.3%);Acute Tox. 4 (67.7%);STOT SE 3 (29.7%)

Safety & protection

Disposal Methods · 3 items

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/

Toxicology

Ecotoxicity Values · 2 items

LD50; Species: Peromyscus maniculatus (Deer Mouse) wild, oral via capsule 1600 mg/kg

EC50; Species: Daphnia magna (Water flea) age 6-24 hr; Conditions: freshwater, static, 20 °C, pH > or =7.0; Concentration: 5000 ug/L for 48 hr (95% confidence interval: 2200-12000 ug/L); Effect: intoxication, immobilization /formulation/

Environmental Fate · 3 items

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).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Effluent Concentrations · 1 item

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).

Soil Adsorption/Mobility · 1 item

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).

Artificial Pollution Sources4-Acetylaniline's production and use as a laboratory reagent(1) may result in its release to the environment through various waste streams(SRC).

Regulatory information

Regulatory InformationChemical: Ethanone, 1-(4-aminophenyl)-

Safety data

PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
AM5500000
hs_code
29223900
Toxicity
LD50 orally in Rabbit: 381 mg/kg

Chemistry & industry

Pharmacology

Mechanism of ActionP-AMINOACETOPHENONE IS KNOWN TO BE A POWERFUL METHEMOGLOBIN-FORMER IN VIVO.

Uses & manufacturing

Uses · 4 items

Used as intermediate for flavaniline (basic dye), acetohexamide, and an oral hypoglycemic drug; [HSDB]

Laboratory reagent

... for treating intoxication with cyanogenic toxic substances

CHEMICAL INTERMEDIATE FOR FLAVANILINE (BASIC DYE), ACETOHEXAMIDE, AND AN ORAL HYPOGLYCEMIC DRUG.

Methods of ManufacturingTRANSFER HYDROGENATION OF P-NITROACETOPHENONE WITH PALLADIUM CATALYST AND CYCLOHEXENE HYDROGEN DONOR
General Manufacturing InformationEthanone, 1-(4-aminophenyl)-: ACTIVE
Applications · 5 items

Description4-Aminoacetophenone is in the form of yellow needle-like crystals, with a melting point of 106°C, a boiling point of 293-295°C, and 195-200°C (2kPa). Soluble in hot water, soluble in alcohol, ether, dilute hydrochloric acid and dilute sulfuric acid, it is slightly soluble in benzene and cold water. Has a special pleasant fragrance. It can be used as a pharmaceutical intermediate.

Uses4'-Aminoacetophenone, is used in pharmaceuticals, medicines and other organic products. It is also used as a reagent for the photometric determination of Ce. As pharmaceutical intemediate or in the determination of palladium and vitaminB1.

Uses4-Aminoacetophenone is a novel utilization of aminophenone derivative in toxicology used for treating intoxications with cyanogenic toxic substances.

Uses4-Aminoacetophenone can be used as an organic reagent to synthesize a variety of organic substances, which is used in the field of anticancer drug preparation and analytical detection. Using it as a raw material, Schiff alkali palladium(II) complexes (cyclopalladiumated compounds) are synthesized by combining metals with carbon atoms. The drug inhibits and kills invasive melanoma cancer cell line (MDA-MB-435)[1]. Hydroxylamine hydrochloride and 4-aminoacetophenone synthesize 4-aminoacetophenone oxime (APO) by oximation reaction, which has a high sensitivity to Organophosphorus (OP)nerve agent mimic-diethylcyanophosphonate. APO can be used to prepare electrochemical sensors with high sensitivity and selectivity to detect OPs[2].

General Description4′-Aminoacetophenone, commonly known as Clenbuterol Impurity D, is a related compound of sympathomimetic amine drug clenbuterol. Clenbuterol belongs to a group of compounds referred to as β-2-agonists and is generally used in the treatment of asthma.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
艾斯提克(山东)生物医药有限公司21-58999881 15623240527 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Related reactions

2,313 records

Compound notes

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