4,4'-Dibromo-2,2'-bipyridine
[CAS# 18511-71-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 4,4'-Dibromo-2,2'-bipyridine
• Synonyms: 4-bromo-2-(4-bromopyridin-2-yl)pyridine
• Molecular Formula: C₁₀H₆Br₂N₂
• Molecular Weight: 313.98
• CAS Registry Number: 18511-71-2
• EC Number: 679-872-5
• SMILES: C1=CN=C(C=C1Br)C2=NC=CC(=C2)Br

Properties

• Density: 1.8±0.1 g/cm³, Calc.^*
• Melting point: 140 °C (Expl.)
• Index of Refraction: 1.639, Calc.^*
• Boiling Point: 362.9±37.0 °C (760 mmHg), Calc.^*
• Flash Point: 173.3±26.5 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

4,4'-Dibromo-2,2'-bipyridine is an important organic compound in the field of coordination chemistry, known for its ability to coordinate with metal ions and form stable complexes. This compound consists of two pyridine rings, each attached to a bromine atom at the 4-position. The molecular formula for 4,4'-dibromo-2,2'-bipyridine is C10H6Br2N2, and its structure allows for significant versatility in coordination chemistry, particularly in the design of metal complexes for various catalytic and sensing applications.

The discovery of 4,4'-dibromo-2,2'-bipyridine can be traced back to the exploration of bipyridine derivatives in the early 20th century. The bipyridine ligand class has long been known for its ability to form stable and versatile complexes with transition metals, which are of great interest for a variety of chemical processes, including catalysis and electrochemical reactions. The introduction of halogenated bipyridine derivatives like 4,4'-dibromo-2,2'-bipyridine further expanded the potential applications of bipyridine ligands, particularly in enhancing the stability and reactivity of the complexes formed.

One of the primary applications of 4,4'-dibromo-2,2'-bipyridine is in the synthesis of metal complexes. This compound is used as a ligand in the preparation of coordination compounds with metals such as palladium, platinum, and copper. These complexes often exhibit interesting properties, such as enhanced catalytic activity in reactions like cross-coupling reactions, which are crucial in organic synthesis. The presence of the bromine atoms in the ligand can also influence the electronic properties of the metal center, making these complexes valuable for fine-tuning reaction conditions in catalytic processes.

In addition to its role in catalysis, 4,4'-dibromo-2,2'-bipyridine has found use in the development of sensors and other materials. Its ability to coordinate with metal ions makes it suitable for creating systems that can detect specific metal ions or react with certain chemical species. This makes the compound useful in environmental monitoring and analytical chemistry, where selective detection of metal ions is essential.

In summary, 4,4'-dibromo-2,2'-bipyridine is a versatile compound with important applications in coordination chemistry, particularly in catalysis and sensor technology. Its ability to form stable metal complexes has made it a valuable tool in various chemical processes, demonstrating its broad utility in both academic research and industrial applications.

References

2024. Cationic Iridium(III) Complexes Bearing Different Bulky N,N′-Chelating Ligands. Journal of Inorganic and Organometallic Polymers and Materials.
DOI: 10.1007/s10904-024-03180-7

2011. A Modular ‘Click' Approach to Substituted 2,2′-Bipyridines. Synlett.
DOI: 10.1055/s-0030-1259304

2009. Studies on bis(halogeno) dioxomolybdenum(VI)-bipyridine complexes: Synthesis and catalytic activity. Dalton Transactions.
DOI: 10.1039/b909075d