4-Aminoacetophenone

• CAS: 99-92-3
• Catalog Number: ACM99923
• Category: Other Products
• Molecular Weight: 135.16g/mol
• Molecular Formula: C8H9NO
• 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
• 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
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Heavy Atom Count: 10
• LogP: 0.83 (LogP);log Kow = 0.83
• 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
• Symbol: GHS07
• 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.

Custom Q&A

What is the molecular formula of 4-Aminoacetophenone?

The molecular formula of 4-Aminoacetophenone is C8H9NO.

What are some synonyms for 4-Aminoacetophenone?

Some synonyms for 4-Aminoacetophenone include 4'-Aminoacetophenone, 4-Aminoacetophenone, and p-Aminoacetophenone.

What is the molecular weight of 4-Aminoacetophenone?

The molecular weight of 4-Aminoacetophenone is 135.16 g/mol.

What is the IUPAC name of 4-Aminoacetophenone?

The IUPAC name of 4-Aminoacetophenone is 1-(4-aminophenyl)ethanone.

What is the InChIKey of 4-Aminoacetophenone?

The InChIKey of 4-Aminoacetophenone is GPRYKVSEZCQIHD-UHFFFAOYSA-N.

How many hydrogen bond donor counts does 4-Aminoacetophenone have?

4-Aminoacetophenone has 1 hydrogen bond donor count.

What is the exact mass of 4-Aminoacetophenone?

The exact mass of 4-Aminoacetophenone is 135.068413911 g/mol.

How many rotatable bond counts does 4-Aminoacetophenone have?

4-Aminoacetophenone has 1 rotatable bond count.

What is the topological polar surface area of 4-Aminoacetophenone?

The topological polar surface area of 4-Aminoacetophenone is 43.1 Å2.

Is 4-Aminoacetophenone a canonicalized compound?

Yes, 4-Aminoacetophenone is a canonicalized compound.