6-Bromochroman-2-one
[CAS# 20921-00-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: 6-Bromochroman-2-one
• Molecular Formula: C₉H₇BrO₂
• Molecular Weight: 227.05
• CAS Registry Number: 20921-00-0
• SMILES: C1CC(=O)OC2=C1C=C(C=C2)Br

Properties

• Solubility: 1481 mg/L (25 ºC water)
• Density: 1.6±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.599, Calc.^*
• Melting point: 87.88 ºC
• Boiling Point: 328.99 ºC, 329.5±31.0 ºC (760 mmHg), Calc.^*
• Flash Point: 153.1±24.8 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-P305+P351+P338

Discovory and Applicatios

6-Bromochroman-2-one is an important organic compound belonging to the class of chromanone derivatives. Chromanones are characterized by a fused benzene and oxygen-containing heterocyclic structure, and their derivatives often exhibit a range of biological and pharmacological properties. The introduction of a bromine atom at the 6-position of the chromanone structure significantly alters its chemical and biological characteristics, making 6-bromochroman-2-one a molecule of interest for various research fields, particularly in medicinal chemistry and materials science.

The discovery of 6-bromochroman-2-one arose from the ongoing exploration of halogenated chromanone derivatives for their unique reactivity and bioactivity. The bromine atom in the molecule is particularly valuable because halogenation can enhance solubility, stability, and lipophilicity, characteristics that are often desired in drug discovery. As a result, the brominated version of chromanone has attracted attention for its potential use in creating bioactive compounds, as well as in materials and organic synthesis.

One of the primary areas of interest for 6-bromochroman-2-one is its application in medicinal chemistry. Chromanone derivatives, including 6-bromochroman-2-one, have been studied for their potential anti-inflammatory, antioxidant, and anticancer properties. These compounds have shown promise as scaffolds for the development of new therapeutic agents targeting various diseases. Specifically, 6-bromochroman-2-one has been explored for its potential to inhibit key enzymes involved in inflammation and cancer cell proliferation. The bromine atom enhances the molecule’s ability to interact with biological targets, which could improve its efficacy in treating conditions such as rheumatoid arthritis, asthma, and certain types of cancer.

In addition to its medicinal applications, 6-bromochroman-2-one has shown potential in the field of materials science. The unique electronic properties of bromine-substituted aromatic compounds make them suitable candidates for use in organic semiconductors and organic light-emitting diodes (OLEDs). The incorporation of a bromine atom into the chromanone structure can enhance charge transfer and stability in organic electronic devices, making 6-bromochroman-2-one a promising material for future advancements in flexible electronics and optoelectronic devices.

The synthetic route to 6-bromochroman-2-one typically involves the bromination of chroman-2-one using bromine or other brominating reagents under controlled conditions. This reaction is designed to selectively introduce the bromine atom at the 6-position of the chromanone ring, leading to the formation of the desired product. The reaction conditions are optimized to ensure high yield and purity, enabling the compound’s use in further research and development.

6-Bromochroman-2-one’s utility extends beyond medicinal and material applications. It can also serve as an intermediate in organic synthesis, where its reactivity can be harnessed to create more complex molecules. This versatility makes 6-bromochroman-2-one an attractive building block for researchers involved in the development of new organic compounds.

In conclusion, 6-bromochroman-2-one is a halogenated chromanone derivative with promising applications in medicinal chemistry, materials science, and organic synthesis. Its biological activity and electronic properties make it a valuable candidate for drug development, cancer treatment, and organic electronics. As research continues, the full potential of this compound is likely to expand, leading to further innovations in therapeutic agents and advanced materials.