3-Acetyl-5-bromopyridine
[CAS# 38940-62-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 3-Acetyl-5-bromopyridine
• Synonyms: 5-Acetyl-3-bromopyridine; 1-(5-Bromopyridin-3-yl)ethanone
• Molecular Formula: C₇H₆BrNO
• Molecular Weight: 200.03
• CAS Registry Number: 38940-62-4
• EC Number: 623-602-0
• SMILES: CC(=O)C1=CC(=CN=C1)Br

Properties

• Density: 1.5±0.1 g/cm³ Calc.^*
• Melting point: 90 - 94 °C (Expl.)
• Boiling point: 279.3±25.0 °C 760 mmHg (Calc.)^*
• Flash point: 122.7±23.2 °C (Calc.)^*
• Index of refraction: 1.558 (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
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

3-Acetyl-5-bromopyridine is a chemical compound that features a pyridine ring with two functional groups attached: an acetyl group at the 3-position and a bromine atom at the 5-position. This compound has been the subject of extensive research due to its valuable chemical structure and potential for applications in various fields, especially in organic synthesis and medicinal chemistry.

The discovery of 3-acetyl-5-bromopyridine is part of the broader exploration of functionalized pyridine derivatives, which are known for their utility in synthetic chemistry. Pyridine itself is a heterocyclic compound widely used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and ligands for coordination chemistry. The acetylation of pyridine at the 3-position and halogenation at the 5-position further increases the chemical versatility of the molecule, allowing it to serve as a key intermediate for a variety of reactions.

The primary method for synthesizing 3-acetyl-5-bromopyridine involves halogenation of the pyridine ring, followed by acetylation. The bromine atom is typically introduced through electrophilic substitution reactions, and the acetyl group is then introduced using acetylating agents such as acetyl chloride or acetic anhydride. This synthetic pathway has been well-documented and is widely used in laboratories for producing this compound at scale.

3-Acetyl-5-bromopyridine finds its main applications in medicinal chemistry, where pyridine derivatives are of significant interest due to their biological activity. The acetyl group enhances the lipophilicity of the molecule, which can improve its pharmacokinetic properties, such as absorption and distribution in biological systems. The bromine atom, on the other hand, can enhance the compound’s reactivity, making it useful in further synthetic modifications.

The compound is often employed as an intermediate in the synthesis of more complex bioactive molecules. For example, it can be used to develop compounds with potential antimicrobial, anticancer, and antiviral activities. By modifying the structure of 3-acetyl-5-bromopyridine, researchers can create a wide range of derivatives that might show promising bioactivity against various targets. These derivatives could have potential applications in drug development, especially in the design of small-molecule inhibitors or other therapeutic agents.

In addition to its use in medicinal chemistry, 3-acetyl-5-bromopyridine is also valuable in the synthesis of coordination complexes. The pyridine ring is an excellent ligand for metal ions, and functionalizing it at specific positions allows for the design of metal-organic frameworks and catalysts. The compound can be used as a ligand in the preparation of catalysts for various organic reactions, such as cross-coupling reactions, which are crucial in the synthesis of pharmaceuticals and other complex organic molecules.

Moreover, the ability to functionalize 3-acetyl-5-bromopyridine further at different positions on the pyridine ring makes it a versatile building block in synthetic chemistry. Its structure is compatible with various synthetic transformations, such as nucleophilic substitution or coupling reactions, making it an important intermediate for the preparation of more complex aromatic compounds. Additionally, the presence of both an acetyl and a bromine group provides multiple sites for further functionalization, increasing the molecule’s potential applications.

In conclusion, 3-acetyl-5-bromopyridine is a valuable compound in organic synthesis, with a broad range of applications in medicinal chemistry and materials science. Its utility as a versatile intermediate allows it to be modified to create a variety of biologically active molecules, particularly in the development of new pharmaceuticals. Furthermore, its ability to serve as a ligand for coordination chemistry enhances its role in the development of new catalysts and materials. The well-established synthetic routes and its functional properties make 3-acetyl-5-bromopyridine an important molecule for ongoing research in multiple fields.

References

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DOI: 10.1055/s-0036-1591523

2012. With Hetaryl Halides in Alcohols. Science of Synthesis, 1.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-031-00062