2-Bromopyridine-5-carbaldehyde
[CAS 149806-06-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 2-Bromopyridine-5-carbaldehyde
• Synonyms: 6-Bromopyridine-3-carboxaldehyde; 6-Bromonicotinaldehyde
• Molecular Formula: C₆H₄BrNO
• Molecular Weight: 186.01
• CAS Registry Number: 149806-06-4
• EC Number: 629-088-4
• SMILES: C1=CC(=NC=C1C=O)Br

Properties

• Melting point: 104-110 °C

Safety Data

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

Hazard Classification

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

Discovery and Applications

2-Bromopyridine-5-carboxaldehyde, with the chemical formula C6H4BrNO and a molecular weight of 186.01 g/mol, is an aromatic aldehyde with a bromine atom at the 2-position and a formyl group at the 5-position of the pyridine ring. This compound combines the reactivity of aldehydes with the unique properties of halopyridines, making it a valuable intermediate in chemical synthesis.

The discovery of 2-bromopyridine-5-carboxaldehyde stems from the study of halopyridines and their derivatives. The development of this compound stems from the need to explore the reactivity of bromopyridines in various organic transformations. The synthetic method involves the selective bromination and formylation of pyridine, allowing the introduction of bromine atoms and aldehyde groups into the aromatic ring. The synthesis of 2-bromopyridine-5-carboxaldehyde generally involves a two-step process: bromination followed by formylation. A common approach is to brominate pyridine at the 2-position using bromine or N-bromosuccinimide (NBS) under controlled conditions and then formylate the resulting 2-bromopyridine at the 5-position using a formylation agent such as Vilsmeier-Haack or Gattermann-Koch formylation. These steps yield 2-bromopyridine-5-carboxaldehyde, which features functional groups that enhance reactivity for further transformations.

2-Bromopyridine-5-carboxaldehyde is used as an intermediate in pharmaceutical synthesis, particularly in the development of heterocyclic compounds. Its bromine and aldehyde groups enable it to participate in reactions such as cross-coupling, providing pathways to a variety of biologically active molecules.

In organic synthesis, this compound is a key building block for making more complex molecules. The aldehyde group can undergo condensation, reduction, and other transformations, while the bromine atom can be substituted or further modified through a variety of organic reactions, facilitating the synthesis of novel compounds.

In materials science, 2-bromopyridine-5-carboxaldehyde is used to synthesize ligands for metal-organic frameworks (MOFs) and coordination compounds. Its ability to form bonds with metals enhances the stability and functionality of these materials, making them useful in catalysis, gas storage, and separation technologies.

This compound serves as a reagent in chemical research, enabling the exploration of reaction mechanisms and the development of new synthetic methods. Its functional groups allow chemists to study a wide range of chemical processes and create innovative molecules with specific properties.

References

2019. Application of the concept of oxime library screening by mass spectrometry (MS) binding assays to pyrrolidine-3-carboxylic acid derivatives as potential inhibitors of gamma-aminobutyric acid transporter 1 (GAT1). Bioorganic & Medicinal Chemistry, 27(13).
DOI: 10.1016/j.bmc.2019.05.001

2019. Screening oxime libraries by means of mass spectrometry (MS) binding assays: Identification of new highly potent inhibitors to optimized inhibitors gamma-aminobutyric acid transporter 1. Bioorganic & Medicinal Chemistry, 27(7).
DOI: 10.1016/j.bmc.2019.02.015

2018. Rhenium and technetium complexes of thioamide derivatives of pyridylhydrazine that bind to amyloid-beta plaques. Journal of Biological Inorganic Chemistry, 23(6).
DOI: 10.1007/s00775-018-1590-4