2-Bromo-4'-iodoacetophenone
[CAS# 31827-94-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic ketone
• Name: 2-Bromo-4'-iodoacetophenone
• Synonyms: 2-Bromo-1-(4-iodophenyl)ethanone
• Molecular Formula: C₈H₆BrIO
• Molecular Weight: 324.94
• CAS Registry Number: 31827-94-8
• SMILES: C1=CC(=CC=C1C(=O)CBr)I

Properties

• Density: 2.1±0.1 g/cm³ Calc.^*
• Boiling point: 328.7±22.0 °C 760 mmHg (Calc.)^*
• Flash point: 152.6±22.3 °C (Calc.)^*
• Index of refraction: 1.649 (Calc.)^*

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

Safety Data

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

Discovery and Applications

2-Bromo-4'-iodoacetophenone is an organic compound belonging to the class of aryl ketones, characterized by the presence of a carbonyl group (C=O) attached to a phenyl ring, with bromine (Br) and iodine (I) atoms as substituents at the 2-position and 4'-position of the aromatic ring, respectively. This compound is a derivative of acetophenone, where the acetyl group (–COCH3) is bonded to the aromatic ring. The presence of halogens on the phenyl ring significantly influences its chemical properties and reactivity.

The halogen atoms, bromine and iodine, provide useful sites for further chemical modification. Both bromine and iodine are known to be reactive in various organic reactions, such as nucleophilic substitution and cross-coupling reactions. The combination of these two halogens at specific positions on the aromatic ring can direct the reactivity of the molecule in a way that makes it a useful intermediate for further chemical synthesis. The iodine atom at the para position (4'-position) and the bromine atom at the ortho position (2-position) are well-positioned to undergo reactions that are of interest in organic chemistry.

2-Bromo-4'-iodoacetophenone is commonly employed as an intermediate in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and materials. The halogenated nature of the compound makes it suitable for palladium-catalyzed cross-coupling reactions, such as the Suzuki or Heck reactions, which can be used to build carbon-carbon bonds. These reactions are fundamental tools in synthetic organic chemistry for constructing more complex structures. The reactivity of the halogen atoms in this compound also allows it to be used in other functional group transformations, such as nucleophilic aromatic substitution reactions.

In medicinal chemistry, the structure of 2-bromo-4'-iodoacetophenone may be of interest as a precursor to bioactive compounds. Halogenated acetophenone derivatives have been investigated for a variety of biological activities, including anti-inflammatory, antimicrobial, and anticancer properties. The specific combination of bromine and iodine may affect how the compound interacts with various biological targets, potentially enhancing its biological activity. As such, this compound could serve as a starting point for the design of novel therapeutic agents.

In summary, 2-bromo-4'-iodoacetophenone is a halogenated aryl ketone that serves as a versatile intermediate in organic synthesis. Its structure, featuring both bromine and iodine substituents, makes it particularly useful for reactions that form carbon-carbon bonds or modify functional groups, which are crucial in the development of pharmaceuticals and other chemical products.

References

2010. 4-Hydroxy-2-[(4-iodobenzoyl)methyl]-3-(3-methoxybenzoyl)-2H-1,2-benzothiazine 1,1-dioxide. Acta Crystallographica Section E: Structure Reports Online, 66(9).
DOI: 10.1107/s1600536810032265

2024. Application of α-bromination reaction on acetophenone derivatives in experimental teaching: a chemical innovation experiment engaging junior undergraduates. BMC Chemistry, 18(1).
DOI: 10.1186/s13065-024-01145-y

2012. Supramolecular Synthesis of Selenazoles Using Selenourea in Water. Science of Synthesis, 1.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-018-00375