기본 정보
- 표준 SMILES
CC(=O)c1ccc(N)cc1- InChIKey
GPRYKVSEZCQIHD-UHFFFAOYSA-N- 분자식
- C8H9NO
- 평균 분자량
- 135.16 g/mol
- 단동위원소 질량
- 135.06841391
이름 및 식별자
- 우선 이름
- p-Aminoacetophenone
- IUPAC
- 1-(4-aminophenyl)ethanone
- 현지명
- p-아미노아세트페논
- 영어명
- 4-Aminoacetophenone
- 분자식
- C8H9NO
- 분자량
- 135.16
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
99-92-3- PubChem CID
- 7468
- DTXSID
DTXSID6052669- ChEMBL
CHEMBL3278329- UNII
- 1S58KH902I
- EC Number
- 202-801-2
- Nikkaji
- J3.228J
물성
구조 계산 물성
- XLogP
- 0.8
- 극성 표면적
- 43.1 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 1
- 무거운 원자 수
- 10
- 형식 전하
- 0
- 복잡도
- 125
실험 및 물리화학적 성질
Color/Form
Yellow monoclinic prisms from alcohol
Yellow needles
Solubility
Soluble in hydrochloric acid
Very soluble in ether and ethanol
In water, 3.35X10+3 mg/L at 37 °C
Kovats Retention Index
1440
2181
물리화학적 성질
- 녹는점
- 103 · 103-107 °C(lit.)
- 끓는 점
- 293 °C · 293 °C(lit.)
- 밀도
- 0 · 0,77 g/cm
- 굴절률
- 1.57 · 1.5700 (estimate)
- 인화점
- 292 · 292-294°C
- 저장 조건
- 30 °C · Store below +30°C.
- 용해도
- 6.5 g/L · 6.5g/L
- 물리적 상태
- 결정성 분말
- 산도 계수 (pKa)
- 2.17 · 2.17±0.10(Predicted)
- Specific Gravity
- 0.77 · 0.77
- 색상
- 약간 노란색~갈색
- 수용성
- 뜨거운 물, 에탄올, 에테르에 용해됩니다.
- Merck
- 14 · 14,413
- BRN
- 471493 · 471493
- Henry's Law Constant
- 2.2 · 2.2×103 mol/(m3Pa) at 25℃, HSDB (2015)
- InChI
- 1S/C8H9NO/c1-6(10)7-2-4-8(9)5-3-7/h2-5H,9H2,1H3
- InChIKey
- GPRYKVSEZCQIHD-UHFFFAOYSA-N
- SMILES
- CC(=O)c1ccc(N)cc1
- LogP
- 0.83 · 0.830
- NIST
- 4 · Acetophenone, 4'-amino-(99-92-3)
- EPA
- 4 · 4'-Aminoacetophenone (99-92-3)
화학적 성질
slightly yellow to brown crystalline powder
안전 및 규제
GHS 분류
GHS Classification
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.
유해성 정보
Hazards Summary
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.
안전 및 보호
Disposal Methods
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/
독성 정보
Ecotoxicity Values
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
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).
Effluent Concentrations
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
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).
Environmental Bioconcentration
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).
Volatilization from Water/Soil
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).
Non-Human Toxicity Excerpts
/LABORATORY ANIMALS: Acute Exposure/ P-AMINOACETOPHENONE ... /WAS/ TESTED IN 0.02 MOLAR AQ SOLN @ PH 6.5 BY DROPPING FOR 10 MIN ON RABBIT CORNEAS FROM WHICH EPITHELIUM HAD BEEN REMOVED. NO SIGNIFICANT CORNEAL OPACITY RESULTED & RECOVERY WAS COMPLETE WITHIN 5 DAYS.
Environmental Abiotic Degradation
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).
규제 정보
안전 데이터
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- AM5500000
- 독성
- LD50 orally in Rabbit: 381 mg/kg
- HS 번호
- 29223900
- risk_code
- 22-36/37/38-20/21/22
- hazard_code
- Xn,Xi
- safety_code
- 26-36
- 위험 등급
- IRRITANT-HARMFUL
- 기존화학 물질
- KE-00081
- Hazard Classifications
- Acute Tox. 4 Oral
- 스토리지 클래스
- 11 - Combustible Solids
- 유해 물질 데이터
- 99-92-3(Hazardous Substances Data)
화학 및 산업
약리 정보
용도 및 제조
Uses
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.
응용 분야
용도4-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].
일반 설명4′-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.
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