872365-91-8 | 2-Bromo-6-(difluoromethyl)pyridine

CAS:872365-91-8 | 2-Bromo-6-(difluoromethyl)pyridine,Description

2-Bromo-6-(difluoromethyl)pyridine is a compound that is part of a broader class of brominated and fluorinated pyridines. These compounds are of significant interest in the field of organic chemistry due to their potential applications in the synthesis of various biologically active molecules and ligands for transition metals. The presence of bromine and difluoromethyl groups in the pyridine ring can influence the reactivity and electronic properties of the molecule, making it a versatile intermediate in organic synthesis.

Synthesis Analysis

The synthesis of brominated pyridine derivatives often involves the use of bromination reactions or metal-halogen exchange processes. For instance, 6-bromo-2-lithiopyridine has been used as an intermediate in the synthesis of 2,6-disubstituted pyridines, where the bromine atom can be replaced through various reactions. Additionally, the synthesis of 6-bromo-imidazo[4,5-b]pyridine derivatives has been achieved through condensation reactions followed by alkylation, demonstrating the versatility of brominated pyridines in constructing complex heterocycles.

Molecular Structure Analysis

The molecular structure of brominated and fluorinated pyridines can be elucidated using techniques such as single-crystal X-ray diffraction. These studies reveal the geometry of the compound in the solid state and provide insights into intermolecular interactions such as hydrogen bonding and π-π interactions. The presence of substituents like bromine and difluoromethyl groups can affect the overall molecular geometry and packing in the crystal lattice.

Chemical Reactions Analysis

Brominated pyridines participate in various chemical reactions, including carbon-carbon coupling, which is a cornerstone in organic synthesis. The reactivity of these compounds can be further explored through their interactions with nucleophiles and their ability to form complexes with transition metals. For example, the synthesis of FeCl2 complexes with brominated pyridine ligands has been reported, highlighting the role of these molecules in coordination chemistry.

Physical and Chemical Properties Analysis

The physical and chemical properties of 2-bromo-6-(difluoromethyl)pyridine and related compounds can be investigated using spectroscopic techniques and computational methods such as density functional theory (DFT). Studies have shown good agreement between experimental spectroscopic data and theoretical calculations, providing a comprehensive understanding of the electronic structure and potential bioactivity of these molecules. Additionally, the nonlinear optical properties of certain brominated pyridines have been computed and found to be significant, suggesting potential applications in materials science.

Scientific Research Applications

Spectroscopic and Density Functional Theory Studies

Research involving similar pyridine derivatives, such as 5-Bromo-2-(trifluoromethyl)pyridine, focuses on their spectroscopic characterization using techniques like FT-IR and NMR spectroscopy. Density Functional Theory (DFT) is applied to explore the molecular structure and vibrational frequencies. These compounds also show potential in nonlinear optical properties and antimicrobial activities (Vural & Kara, 2017).

Crystal and Molecular Structure Analysis

The crystal and molecular structures of pyridine derivatives such as 6-bromo-2-(furan-2-yl)-3-(prop-2-ynyl)-3H-imidazo[4,5-b]pyridine have been investigated using single-crystal X-ray diffraction. This study focuses on molecular geometry in the solid state and intermolecular interactions within the crystal packing (Rodi et al., 2013).

Synthesis of Pyridine Derivatives

Syntheses involving pyridyllithium reagents, including 6-bromo-2-lithiopyridine, have been explored to create new 2,6-disubstituted pyridine derivatives. These syntheses utilize various reactions such as metal-halogen exchange, highlighting the versatility of pyridine derivatives in organic synthesis (Parks, Wagner, & Holm, 1973).

Ligand Synthesis for Metal Complexes

Studies on ligands like [(6-bromo 2-pyridylmethyl) (6-fluoro 2-pyridylmethyl) (2-pyridylmethyl)] amine demonstrate the synthesis and application of pyridine-based ligands in forming metal complexes. Such research often explores the coordination modes and electrochemical properties of these complexes (Benhamou et al., 2011).

Applications in Corrosion Inhibition

Pyridine derivatives are used in corrosion inhibition studies. For instance, a pyridine derivative's adsorption and inhibitory effects on mild steel corrosion in acidic media have been explored, demonstrating the compound's protective properties and potential applications in material science (Saady et al., 2020).

Safety And Hazards

“2-Bromo-6-(difluoromethyl)pyridine” is classified as Acute Tox. 3 Oral, Eye Irrit. 2, and Skin Irrit. 2. It has a hazard statement of H301 - H315 - H319, indicating that it is toxic if swallowed, causes skin irritation, and causes serious eye irritation. The compound should be handled with appropriate safety measures, including wearing protective gloves, eye protection, and face protection.

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