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4-Aminoacetophenone

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
Color/Form
Yellow monoclinic prisms from alcohol;Yellow needles
Complexity
125
Covalently-Bonded Unit Count
1
EC Number
202-801-2
Exact Mass
135.068414g/mol
Formal Charge
0
Hazard Statements
Xn,Xi
Heavy Atom Count
10
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
1
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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