4,4′-Bis(bromomethyl)-2,2′-bipyridine

4,4′-Bis(bromomethyl)-2,2′-bipyridine

CAS Number: 134457-14-0

Molecular Formula: C₁₂H₁₀Br₂N₂

Synonyms: 4,4′-Bis(bromomethyl)-bipyridine

Chemical Characteristics

This compound consists of a bipyridine backbone with bromomethyl groups (-CH₂Br) at the 4,4′-positions.

It features both:

• Coordinating nitrogen atoms (from the bipyridine rings), and

• Reactive bromomethyl groups that can undergo nucleophilic substitution reactions.

Therefore, it serves as a bifunctional building block useful for both metal coordination and organic functionalization.

Main Applications and Functions

1️⃣ Ligand Synthesis

• A key intermediate for the preparation of functionalized bipyridine ligands.

• Commonly used to construct transition metal complexes such as those of Ru(II), Ir(III), Fe(II), etc.

• These complexes are widely applied in:

  • Photocatalysis

  • Electrochemical sensors

  • Luminescent materials (OLEDs, fluorescent probes)

  • Dye-sensitized solar cells (DSSCs)

Example:

Used to synthesize bridge-type ligands like [Ru(bpy)₂(L)]²⁺, which act as photo- and electron-transport materials.

2️⃣ Organic Intermediate

• The bromomethyl groups are excellent electrophilic sites, capable of reacting with amines, alcohols, or thiols.

• It is used to synthesize:

  • Quaternary ammonium derivatives

  • Polymerizable monomers with bipyridine backbones

  • Bridging ligands and crosslinking agents

  • Functional molecules for optical or ion-recognition applications

3️⃣ Material Chemistry and Functional Molecule Construction

• Applied in the preparation of:

  • Photoelectric conversion materials (light-harvesting dyes)

  • Metal–organic frameworks (MOFs) and coordination polymers (CPs)

  • Fluorescent probes and chemical sensors

Handling and Storage

• Contains reactive bromine groups; handle with care.

• Store in a cool, dry, and light-protected environment.

• Avoid exposure to moisture or alkaline conditions.

✅ Summary

4,4′-Bis(bromomethyl)-2,2′-bipyridine (CAS 134457-14-0)

is a bifunctional bipyridine derivative used mainly as:

• A precursor for ligand synthesis and metal complex formation,

• An intermediate for photoelectric and catalytic materials, and

• A building block for organic and polymeric frameworks.

It is widely utilized in photocatalysis, luminescent materials, coordination chemistry, and MOF research.