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4-Aminoacetophenone

CAS No.
99-92-3
Chemical Name:
4-Aminoacetophenone
Synonyms
1-(4-AMINOPHENYL)ETHAN-1-ONE;1-(4-AMINOPHENYL)ETHANONE;P-AMINOACETOPHENONE;4-ACETYLANILINE;p-Acetylaniline;P-AMINOACETYLBENZENE;1-(4-aminophenyl)-ethanon;NSC 3242;usafek-631;USAF EK-631
CBNumber:
CB9299995
Molecular Formula:
C8H9NO
Molecular Weight:
135.16
MDL Number:
MFCD00007896
MOL File:
99-92-3.mol
MSDS File:
SDS
Last updated:2024-12-18 14:15:30

4-Aminoacetophenone Properties

Melting point 103-107 °C(lit.)
Boiling point 293 °C(lit.)
Density 0,77 g/cm
refractive index 1.5700 (estimate)
Flash point 292-294°C
storage temp. Store below +30°C.
solubility 6.5g/l
form Crystalline Powder
pka 2.17±0.10(Predicted)
color Slightly yellow to brown
Specific Gravity 0.77
Water Solubility It is soluble in hot water, ethanol and ether.
Merck 14,413
BRN 471493
InChIKey GPRYKVSEZCQIHD-UHFFFAOYSA-N
LogP 0.830
CAS DataBase Reference 99-92-3(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 1S58KH902I
NIST Chemistry Reference Acetophenone, 4'-amino-(99-92-3)
EPA Substance Registry System 4'-Aminoacetophenone (99-92-3)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P501
Hazard Codes  Xn,Xi
Risk Statements  22-36/37/38-20/21/22
Safety Statements  26-36
WGK Germany  3
RTECS  AM5500000
TSCA  T
HazardClass  IRRITANT-HARMFUL
HS Code  29223900
Hazardous Substances Data 99-92-3(Hazardous Substances Data)
Toxicity LD50 orally in Rabbit: 381 mg/kg
NFPA 704
1
2 0

4-Aminoacetophenone price More Price(37)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A38002 4′-Aminoacetophenone 99% 99-92-3 25g $47.8 2024-03-01 Buy
Sigma-Aldrich A38002 4′-Aminoacetophenone 99% 99-92-3 100g $113 2024-03-01 Buy
TCI Chemical A0251 4'-Aminoacetophenone >98.0%(T) 99-92-3 25g $64 2024-03-01 Buy
TCI Chemical A0251 4'-Aminoacetophenone >98.0%(T) 99-92-3 100g $190 2024-03-01 Buy
Alfa Aesar A13213 4'-Aminoacetophenone, 99% 99-92-3 25g $26.65 2024-03-01 Buy
Product number Packaging Price Buy
A38002 25g $47.8 Buy
A38002 100g $113 Buy
A0251 25g $64 Buy
A0251 100g $190 Buy
A13213 25g $26.65 Buy

4-Aminoacetophenone Chemical Properties,Uses,Production

Description

4-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.
4-Aminoacetophenone

Applications

4′-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.

Synthesis

Through a Williamson ether synthesis method and Smiles rearrangement reaction, benzamide compounds are produced, then the 4-aminoacetophenone preparation is finished after hydrolysis. 

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. acids, Incompatible to Acid chlorides, Acid anhydrides, Chloroformates, Strong oxidizing agents, Strong reducing agents. Stable under ordinary conditions.

Chemical Properties

slightly yellow to brown crystalline powder

Uses

4'-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.

Uses

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

Uses

4-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].

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 34, p. 2013, 1986 DOI: 10.1248/cpb.34.2013
Tetrahedron Letters, 27, p. 4687, 1986 DOI: 10.1016/S0040-4039(00)85038-8

General Description

4′-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.

Safety Profile

Poison by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NO,. See also AROMATIC AMINES

Purification Methods

It is soluble in hot H2O. UV (EtOH) has max 403nm (log 4.42) [Johnson J Am Chem Soc 75 2720 1953]. [Vandenbelt Anal Chem 26 726 1954.] The 2,4-dinitrophenylhydrazone has m 266-267o (from CHCl3 or EtOH) with 403nm (log 4.42), and the max semicarbazone has m 193-194o(dec)(from MeOH). The hydrochloride has m 98o(dec)(from H2O). [Beilstein 14 IV 100.]

Toxicity evaluation

Harmful if swallowed. Causes eye, skin, and respiratory tract irritation. May cause methemoglobinemia.

References

[1] SARTO& L, et al. Anticancer Potential of Palladium(II) Complexes With Schiff Bases Derived from 4-Aminoacetophenone Against Melanoma In Vitro. Anticancer Research, 2019; 39.
[2] Huixiang W, et al. A non-enzymatic electro-chemical sensor for organophosphorus nerve agents mimics and pesticides detections. Organic Electronics, 2017; 252: 1118-1124.

100-19-6
99-92-3
589-16-2
Synthesis of 4-Aminoacetophenone from 4-Nitroacetophenone
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View Lastest Price from 4-Aminoacetophenone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
4-Aminoacetophenone pictures 2024-12-23 4-Aminoacetophenone
99-92-3
US $0.00 / KG 1KG 99% 300mt Jinan Finer Chemical Co., Ltd
4-Aminoacetophenone pictures 2024-12-23 4-Aminoacetophenone
99-92-3
US $0.00 / G 1G 99% 20 CONTIDE BIOTECH CO.,LTD
4-Aminoacetophenone  pictures 2024-12-23 4-Aminoacetophenone
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US $0.00-0.00 / kg 1kg 99%+ 10000kgs per Month Shanghai Qyubiotech Co., Ltd.
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