2,4-Difluoroiodobenzene

Base Information

• Chemical Name: 2,4-Difluoroiodobenzene
• CAS No.: 2265-93-2
• Molecular Formula: C6H3F2I
• Molecular Weight: 239.991
• Hs Code.: 29039990
• Mol file: 2265-93-2.mol

Synonyms:1-Iodo-2,4-difluorobenzene;2,4-Difluoro-1-iodobenzene;NSC 68264;

Chemical Property of 2,4-Difluoroiodobenzene

Chemical Property:

• Appearance/Colour: clear light yellow to slightly brown liquid
• Vapor Pressure: 1.2mmHg at 25°C
• Refractive Index: n20/D 1.557(lit.)
• Boiling Point: 180.6 °C at 760 mmHg
• Flash Point: 67.8 °C
• PSA: 0.00000
• Density: 2.001 g/cm³
• LogP: 2.56940
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• Water Solubility.: INSOLUBLE

Purity/Quality:

99% ^*data from raw suppliers

2,4-difluoro-1-iodobenzene 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 2,4-Difluoroiodobenzene is a versatile aryl halide reagent used in N-arylation reactions with nitrogen heterocycles, such as pyrazoles, imidazoles, and pyrroles, under copper catalysis or nucleophilic aromatic substitution (SNAr) conditions. It enables regioselective and multiple substitutions to form diverse N-arylated heterocycle derivatives, which can be further functionalized via cross-coupling reactions like Suzuki–Miyaura. The compound's reactivity and structural features are confirmed through spectroscopic (NMR, IR, MS) and crystallographic analyses, highlighting its utility in synthetic organic chemistry.

Technology Process of 2,4-Difluoroiodobenzene

There total 7 articles about 2,4-Difluoroiodobenzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

2,4-difluorophenylboronic acid (144025-03-6) → 2,4-difluoro-1-iodobenzene (2265-93-2)

Guidance literature:

With iodine; potassium carbonate; In acetonitrile; at 80 ℃; for 14h; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1055/s-0033-1340871

Reference yield: 48.0%

2,6-difluoroiodobenzene (13697-89-7) → 2,4-difluoro-1-iodobenzene (2265-93-2)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -75 ℃;

DOI:10.1002/1099-0690(200210)2002:19<3351::AID-EJOC3351>3.0.CO;2-I

Reference yield:

2,6-difluoroiodobenzene (13697-89-7) + acetonitrile (75-05-8,26809-02-9) → iodoacetonitrile (624-75-9) + 1,3-Difluorobenzene (372-18-9) + 2,4-difluoro-1-iodobenzene (2265-93-2)

Guidance literature:

for 24h; Product distribution; Irradiation;

DOI:10.1246/bcsj.70.1875

upstream raw materials:

2,4-difluorophenylamine

2,6-difluoroiodobenzene

acetonitrile

1,3-Difluorobenzene

Downstream raw materials:

2,4-Difluoro-1-(4-isopropyl-phenoxy)-benzene

1-(4-tert-Butyl-phenoxy)-2,4-difluoro-benzene

2,4-difluorofluorenone

2,4-Difluor-7-nitro-9-oxo-fluoren

Refernces

N-Arylation of nitrogen heterocycles with 2,4-difluoroiodobenzene

10.1016/j.tet.2008.11.036

The research primarily focuses on the arylation reactions of NH-heterocycles, such as pyrazole, 3-(trifluoromethyl)pyrazole, imidazole, and pyrrole, with 2,4-difluoroiodobenzene, facilitated by both copper catalysis and SNAr reactions. The study aims to explore the regioselective reactions and multiple substitutions to synthesize a range of new N-arylated heterocycle derivatives. The reactants include various NH-heterocycles and 2,4-difluoroiodobenzene, with copper catalysts like Cu2O and ligands such as salicylaldoxime utilized in some reactions. The analyses involved the use of 1H, 13C, and 19F NMR spectroscopy, IR spectroscopy, and mass spectrometry to determine the structures and purities of the synthesized compounds, along with X-ray crystallography for certain products to confirm their regiochemistry. The research also includes a Suzuki–Miyaura reaction to extend the utility of the synthesized arylation products.