CAS 99-92-3 4-Aminoacetophenone - Materials / Alfa Chemistry

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4-Aminoacetophenone

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Catalog Number

ACM99923

CAS Number

99-92-3

Product Name

4-Aminoacetophenone

Structure

Category

Liquid Crystal (LC) Building Blocks

Synonyms

1-(4-aminophenyl)-ethanon;1-(4-aminophenyl)ethanone[qr];4'-amino-acetophenon;4'-aminoacetophenone[qr];Acetophenone, p-amino-;Acetophenone,4'-amino-;acetophenone,4-amino-[qr];acetophenone,p-amino-[qr]

IUPAC Name

1-(4-aminophenyl)ethanone

Molecular Weight

135.16g/mol

Molecular Formula

C8H9NO

Canonical SMILES

CC(=O)C1=CC=C(C=C1)N

InChI

InChI=1S/C8H9NO/c1-6(10)7-2-4-8(9)5-3-7/h2-5H,9H2,1H3

InChI Key

GPRYKVSEZCQIHD-UHFFFAOYSA-N

Boiling Point

294.0 °C;294 °C; 195 °C at 15 mm Hg

Melting Point

106 °C

Flash Point

292-294°C

Density

0,77 g/cm

Solubility

Soluble in hydrochloric acid;Very soluble in ether and ethanol;In water, 3.35X10+3 mg/L at 37 °C

Application

4-Aminoacetophenone is a slightly yellow to brown crystalline powder that serves as a versatile organic reagent in the synthesis of various substances. It is prominently utilized in anticancer drug preparation, where it aids in the formation of Schiff alkali palladium(II) complexes, known to inhibit and kill invasive melanoma cancer cell lines like MDA-MB-435. Additionally, through an oximation reaction with hydroxylamine hydrochloride, it forms 4-aminoacetophenone oxime (APO), which is sensitive to Organophosphorus (OP) nerve agent mimics and can be employed to create highly selective and sensitive electrochemical sensors for OP detection. With a melting point of 106°C and a boiling point of 293-295°C, 4-Aminoacetophenone dissolves in hot water, alcohol, ether, dilute acids, and has limited solubility in benzene and cold water, accompanied by a unique pleasant fragrance. This compound finds applications as a pharmaceutical intermediate and in the photometric determination of cerium, as well as in the assessment of palladium and vitamin B1.

Color/Form

Yellow monoclinic prisms from alcohol;Yellow needles

Complexity

125

Covalently-Bonded Unit Count

EC Number

202-801-2

Exact Mass

135.068414g/mol

Formal Charge

Hazard Statements

Xn,Xi

Heavy Atom Count

Log P

0.83 (LogP);log Kow = 0.83

MeSH Entry Terms

4-aminoacetophenone;p-aminoacetophenone;para-aminoacetophenone

Monoisotopic Mass

135.068414g/mol

NSC Number

3242

Odor

Pleasant, characteristic odor

Other Experimental

Henry's Law constant = 4.45X10-9 atm-cu m/mole at 25 °C (est);Hydroxyl radical reaction rate constant = 1.05X10-10 cu cm/molec-sec at 25 °C (est)

Rotatable Bond Count

Safety Description

26-36

Supplemental Hazard Statements

H335-H315-H319-H302

UNII

1S58KH902I

Vapor Pressure

4.32X10-4 mm Hg at 25 °C (est)

XLogP3

0.8

Case Study

Synthesis And Application of 4-Aminoacetophenone-Derived Schiff Base Complexes

Sarto, Luis Eduardo, et al. Anticancer Research, 2019, 39(12), 6693-6699.

Schiff bases derived from 4-aminoacetophenone can be further used to develop anticancer drugs against melanoma when complexed with Pd(II) complexes. The prepared 4-aminoacetophenone-derived Schiff base palladium(II) complex exhibits positive cytotoxic effects on MDA-MB-435, an aggressive melanoma cancer cell line, and may be a candidate for antitumor drug development Promising candidates.
Synthesis of 4-aminoacetophenone-derived Schiff base ligands
· A solution of p-anisaldehyde (8.28 mmol), terephthaldehyde (4.13 mmol) or trans-cinnamaldehyde (8.26 mmol) in ethanol (5 ml), was added dropwise to a solution of of 4- aminoacetophenone (8.28 mmol) in ethanol (30 ml), to yield the L1, L2 and L3 ligands respectively.
· The reaction mixture was stirred at room temperature for 4 h. After coolling for 24 h, at -10˚C, a pellet was formed which was filtered off, washed (with ethanol, water and ethyl ether) and vacuum-dried.

Synthesis of Azo Dyes Derived from 4-Aminoacetophenone

Al-Obaidi,et al. Journal of Biochemical Technology, 2018, 9(4), 33.

New azo dyes can be synthesized through the coupling reaction of p-aminoacetophenone and phenolic formaldehyde. For example, products A1, A2, A4 and A5 are dyes used in the dyeing process and are suitable for wool, cotton and sawdust. In addition to the dyeing process, the dyeing compounds exhibit moderate to good wash fastness and a noticeable smoothness after washing.
Preparation of 4-aminoacetophenone-derived azo compounds
· Preparing diazonium salt
2 ml Conc. HCl with 10 ml distilled water were dissolved in 0.54 g-0.004 mol of p-Amino acetophenone at 0-5 ° C. In the second flask solution was prepared by dissolving 0.200 g of sodium nitrite in 5 ml of distilled water at 0-5 °C; then the first solution was added to the second solution as batches at 0-5 °C.
· Coupling Reaction
In 5 ml of 35% NaOH 0.360 g - 0.004 mol of phenol was dissolved at 0-5 °C and then diazonium salt was added with stirrer at 0-5 °C to obtained yellow precipitate. Finally, the precipitate was collected and the yield was calculated.

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