1-(4-Bromo-3-fluorophenyl)ethanone
[CAS# 304445-49-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic ketone
• Name: 1-(4-Bromo-3-fluorophenyl)ethanone
• Molecular Formula: C₈H₆BrFO
• Molecular Weight: 217.04
• CAS Registry Number: 304445-49-6
• EC Number: 822-357-9
• SMILES: CC(=O)C1=CC(=C(C=C1)Br)F

Properties

• Density: 1.5±0.1 g/cm³ Calc.^*
• Boiling point: 263.3±25.0 °C 760 mmHg (Calc.)^*
• Flash point: 113.0±23.2 °C (Calc.)^*
• Index of refraction: 1.534 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety 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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

1-(4-Bromo-3-fluorophenyl)ethanone is an organic compound that consists of a phenyl group substituted with a bromine atom at the 4-position, a fluorine atom at the 3-position, and an ethanone functional group (-COCH3) attached to the phenyl ring. This compound belongs to the class of aryl ketones, which are characterized by the presence of a carbonyl group (C=O) attached to an aryl group (a benzene ring or a substituted benzene ring).

The structure of 1-(4-bromo-3-fluorophenyl)ethanone is significant due to the combination of halogen substituents, which affect the compound's electronic properties and reactivity. Specifically, the bromine atom at the para position (4-position) and the fluorine atom at the meta position (3-position) influence the electron distribution on the aromatic ring, making it more reactive towards nucleophilic substitution reactions or electrophilic aromatic substitution reactions.

This compound is primarily used as an intermediate in organic synthesis. The combination of halogen substituents on the aromatic ring allows for selective reactivity in the synthesis of more complex molecules. For instance, the presence of both bromine and fluorine atoms can facilitate cross-coupling reactions, such as Suzuki or Heck reactions, which are often employed to form carbon-carbon bonds in the synthesis of pharmaceuticals, agrochemicals, or materials. Furthermore, the ethanone group (-COCH3) in the structure provides an additional point of reactivity that can be utilized for the introduction of other functional groups or modifications.

1-(4-Bromo-3-fluorophenyl)ethanone may also find applications in the development of bioactive compounds. Aryl ketones and their derivatives have been studied for a variety of biological activities, including anti-inflammatory, anti-cancer, and anti-microbial properties. The halogenated nature of this compound could influence its interactions with enzymes, receptors, or other molecular targets, potentially making it a candidate for further investigation in medicinal chemistry.

In summary, 1-(4-bromo-3-fluorophenyl)ethanone is a halogenated aryl ketone that serves as a valuable intermediate in organic synthesis. Its structure, with bromine and fluorine substituents, makes it an important compound for the development of complex molecules in pharmaceuticals, agrochemicals, and other chemical industries. While primarily used in synthetic chemistry, it holds potential for further exploration in the design of bioactive compounds.

References

2023. A pharmacophore-based approach to demonstrating the scope of alcohol dehydrogenases. Bioorganic & Medicinal Chemistry, 82.
DOI: 10.1016/j.bmc.2023.117255