1-(4-Amino-3,5-dichlorophenyl)-2-bromoethanone
[CAS# 37148-47-3]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 1-(4-Amino-3,5-dichlorophenyl)-2-bromoethanone
• Synonyms: 4-Amino-3,5-dichlorophenacyl bromide; 4-Amino-omega-bromo-3',5'-dichloroacetophenone
• Molecular Formula: C₈H₆BrCl₂NO
• Molecular Weight: 282.95
• CAS Registry Number: 37148-47-3
• EC Number: 253-367-6
• SMILES: C1=C(C=C(C(=C1Cl)N)Cl)C(=O)CBr

Properties

• Solubility: Practically insoluble (0.031 g/L) (25 °C), Calc.^*
• Density: 1.764±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 140-142 °C^**

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** Xing, Rui-Juan

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

1-(4-Amino-3,5-dichlorophenyl)-2-bromoethanone, a synthetic organic compound, was discovered through systematic research aimed at developing new pharmacologically active molecules. The compound's synthesis involves the bromination of a precursor molecule, followed by selective amination. This particular structure, characterized by the presence of both bromine and amino functional groups on a dichlorophenyl ring, was designed to enhance specific chemical reactivity and biological activity. The discovery of 1-(4-Amino-3,5-dichlorophenyl)-2-bromoethanone is a result of ongoing efforts to explore novel compounds with potential therapeutic applications, highlighting the innovative approaches in organic and medicinal chemistry.

1-(4-Amino-3,5-dichlorophenyl)-2-bromoethanone has shown significant potential in pharmaceutical development. Its unique structure makes it a valuable intermediate in the synthesis of various therapeutic agents. The amino and bromo groups facilitate the formation of complex molecular frameworks, which are essential in the design of drugs with specific biological activities. Researchers have been exploring its derivatives for their potential as anti-inflammatory, anticancer, and antiviral agents. The compound's ability to modulate biological pathways makes it a promising candidate in the development of new medications targeting a range of diseases.

In chemical research, 1-(4-Amino-3,5-dichlorophenyl)-2-bromoethanone serves as a versatile reagent. Its reactive sites enable a wide array of chemical transformations, making it useful in the synthesis of more complex organic molecules. It is often employed in studying reaction mechanisms and developing new synthetic methodologies. The compound's structure allows for the exploration of novel chemical reactions, contributing to advancements in organic synthesis and the discovery of new materials.

The agrochemical industry benefits from the properties of 1-(4-Amino-3,5-dichlorophenyl)-2-bromoethanone 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 compound's stability and reactivity are leveraged to enhance the potency and selectivity of agrochemical products, thereby improving agricultural productivity and sustainability.

In biomedical research, 1-(4-Amino-3,5-dichlorophenyl)-2-bromoethanone is utilized 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. The insights gained from such studies are crucial for the development of innovative treatments and diagnostic tools.

References

2020. Synthesis and Pharmacokinetics of 2-(4-amino-3,5-dichlorophenyl)-2-(alkylamino)ethanols - Structural Isomers of β2 Agonists Clenproperol and Clenpenterol. Pharmaceutical Chemistry Journal, 54(7).
DOI: 10.1007/s11094-020-02271-2

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