6-Bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one
[CAS# 1242157-15-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Isoquinoline compound
• Name: 6-Bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one
• Molecular Formula: C₉H₇BrFNO
• Molecular Weight: 244.06
• CAS Registry Number: 1242157-15-8
• EC Number: 892-881-0
• SMILES: C1CNC(=O)C2=C1C=C(C=C2F)Br

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.579, Calc.^*
• Boiling Point: 460.1±45.0 ºC (760 mmHg), Calc.^*
• Flash Point: 232.1±28.7 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovory and Applicatios

6-Bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one is a heterocyclic compound that belongs to the class of isoquinolinones, which are known for their diverse biological activities and their role as key intermediates in organic synthesis. This compound features a bromo and a fluoro substituent at the 6th and 8th positions of the isoquinoline ring, respectively, and a carbonyl group at position 1 of the bicyclic structure. Isoquinolinones like 6-bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one have drawn attention in medicinal chemistry due to their potential pharmacological properties.

The discovery of 6-bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one is a part of the ongoing exploration of isoquinoline derivatives for their ability to interact with biological targets. The development of this compound, as with other isoquinoline-based molecules, involved modifications of the isoquinoline structure to introduce functional groups capable of altering biological activity. The incorporation of bromine and fluorine atoms into the molecular structure plays an essential role in modulating the compound’s electronic properties, which affects its reactivity and interaction with cellular targets.

In terms of its applications, 6-bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one has shown potential in the development of therapeutic agents. The isoquinolinone framework is a common scaffold in drug discovery because of its ability to bind to various biological receptors and enzymes. The halogen substitutions at the 6th and 8th positions enhance the lipophilicity and stability of the compound, which can improve its pharmacokinetic properties, such as absorption, distribution, metabolism, and excretion (ADME) characteristics. These modifications can also improve the compound's affinity for specific molecular targets, such as kinases, receptors, or enzymes involved in cancer, neurological disorders, or cardiovascular diseases.

6-bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one has also been explored for its use in the synthesis of complex organic molecules. Its functionalized isoquinoline structure serves as a versatile intermediate in the design of more elaborate compounds with potential therapeutic benefits. The ability to selectively introduce halogen substituents in the synthesis of this compound offers synthetic chemists a valuable tool for tuning the reactivity of the molecule, making it a key building block in medicinal chemistry.

In addition to pharmaceutical applications, this compound's structural features, including its bicyclic system and carbonyl group, make it valuable in the synthesis of new materials, such as conductive polymers or molecular sensors. Isoquinolinone derivatives are known to exhibit interesting optical and electronic properties, and their use in materials science is an emerging area of research. Further investigation into 6-bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one could reveal additional applications in electronics, optics, and other advanced technologies.

Continued studies on the biological and chemical properties of 6-bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one are expected to enhance the understanding of its potential as a therapeutic agent and as a synthetic intermediate. This compound exemplifies the value of halogenated isoquinolinones in drug discovery and materials science, offering a promising platform for further development.