4'-Amino-3',5'-dichloroacetophenone
[CAS# 37148-48-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic ketone
• Name: 4'-Amino-3',5'-dichloroacetophenone
• Synonyms: 4-Acetyl-2,6-dichloroaniline; 1-(4-Amino-3,5-dichlorophenyl)-ethanone; 3',5'-Dichloro-4'-aminoacetophenone
• Molecular Formula: C₈H₇Cl₂NO
• Molecular Weight: 204.05
• CAS Registry Number: 37148-48-4
• EC Number: 253-368-1
• SMILES: CC(=O)C1=CC(=C(C(=C1)Cl)N)Cl

Properties

• Melting point: 161-165 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

4'-Amino-3',5'-dichloroacetophenone is a synthetic organic compound that emerged from systematic research focused on developing new pharmacologically active molecules. This compound was synthesized through the acetylation of 4-amino-3,5-dichlorophenol, which introduces an acetyl group to the phenol, followed by selective chlorination. The discovery of 4'-Amino-3',5'-dichloroacetophenone is a result of ongoing efforts to explore new chemical entities with potential therapeutic applications. Its unique structure, characterized by the presence of both amino and dichloro groups, contributes to its significant biological activity and chemical reactivity, making it a valuable compound in organic and medicinal chemistry.

4'-Amino-3',5'-dichloroacetophenone plays a crucial role in pharmaceutical development due to its potential as an intermediate in the synthesis of various therapeutic agents. The amino and dichloro groups facilitate the formation of complex molecular frameworks, which are essential in designing drugs with specific biological activities. This compound is often explored for its derivatives that exhibit anti-inflammatory, anticancer, and antimicrobial properties. Its ability to interact with different biological targets makes it a promising candidate in the development of new medications for a variety of diseases, including cancer, infections, and inflammatory disorders.

In the realm of chemical research, 4'-Amino-3',5'-dichloroacetophenone is utilized as a versatile reagent. Its reactive sites enable a wide array of chemical transformations, making it valuable in the synthesis of more complex organic molecules. Researchers use this compound to study reaction mechanisms and develop new synthetic methodologies. Its structure allows for the exploration of novel chemical reactions, contributing to advancements in organic synthesis and the discovery of new materials. It serves as a key building block in the development of heterocyclic compounds, which are widely used in pharmaceuticals and materials science.

The agrochemical industry benefits from the properties of 4'-Amino-3',5'-dichloroacetophenone in the development of pesticides and herbicides. Its efficacy in disrupting biological processes in pests and weeds makes it a valuable component in formulations aimed at protecting crops. The stability and reactivity of this compound enhance the potency and selectivity of agrochemical products, thereby improving agricultural productivity and sustainability. It is used to create effective solutions for crop protection, ensuring better yields and reduced environmental impact.

In biomedical research, 4'-Amino-3',5'-dichloroacetophenone is employed in the study of cellular processes and molecular interactions. Its structural attributes enable the investigation of enzyme inhibition, receptor binding, and signal transduction pathways. Researchers use this compound to understand the biochemical underpinnings of various diseases, aiding in the identification of new therapeutic targets. Insights gained from such studies are crucial for developing innovative treatments and diagnostic tools. Its role in elucidating the mechanisms of action of different biological pathways makes it a valuable tool in biomedical research.

References

2024. Synthesis, characterization, and anticancer activity of syringaldehyde-derived chalcones against female cancers. Medicinal Chemistry Research, 33(3).
DOI: 10.1007/s00044-024-03195-2

2021. Synthesis and characterization of new methacrylate copolymers having pendant chloroacetophenon; monomer reactivity ratio, thermal degradation kinetics and biological activity. Polymer Bulletin, 78(10).
DOI: 10.1007/s00289-021-03934-0

2021. Synthesis of β2-Agonist Metabolites of 2-(4-Amino-3,5-Dichlorophenyl)-2-(Alkylamino)Ethanols and their Excretion with Urine in Comparison to the Initial Compounds. Pharmaceutical Chemistry Journal, 55(2).
DOI: 10.1007/s11094-021-02390-4