2,4-Difluoroiodobenzene

• Catalog: OFC2265932
• CAS: 2265-93-2
• Category: Aromatic Fluorocarbons
• Synonyms: 2,4-Difluoro-1-iodobenzene
• Purity: 98+%
• MDL Number: MFCD00040151

• Molecular Weight: 239.99
• Boiling Point: 175-176°C
• Flash Point: 67°C
• Density: 2.006g/cm³
• Refractive Index: 1.5574

• Hazards: Irritant
• Hazard Statements: May cause respiratory irritation.|Causes skin irritation.|Causes serious eye irritation.

Case Study

N-Arylation of Nitrogen Heterocycles Using 2,4-Difluoroiodobenzene via SNAr and Ullmann-Type Coupling

Jitchati R, et al. Tetrahedron, 2009, 65(4,) 855-861.

2,4-Difluoroiodobenzene has been exploited as a bifunctional arylating agent for the N-arylation of nitrogen heterocycles, including pyrazole, 3-(trifluoromethyl)pyrazole, imidazole, and pyrrole. The study demonstrated dual reactivity: SNAr displacement at the C-F bonds and Cu-catalyzed Ullmann-type coupling at the C-I position. Reactions were conducted under both metal-free and copper(I)-mediated conditions, with regioselectivity controlled by the intrinsic reactivity of the heterocycle and the electronic properties of the aryl halide. The experimental procedure involved heating the heterocycle with 2,4-difluoroiodobenzene in the presence of CuI and base in DMSO, yielding mono- and disubstituted N-arylated products. These results highlight the synthetic utility of 2,4-difluoroiodobenzene in building structurally diverse heteroaryl scaffolds through site-selective functionalization.