1369829-80-0

Usage

Type of compound

Substituted benzene compound

Structure

a. Bromine atom at the 1 position
b. Fluorine atom at the 2 position
c. tert-Butyl group at the 4 position

Applications

a. Intermediate in the synthesis of pharmaceuticals
b. Intermediate in the synthesis of agrochemicals
c. Intermediate in the synthesis of materials
d. Building block in the production of various chemicals

Usage

Primarily used in organic synthesis

Stability

Relatively stable

Reactivity

Low reactivity

Importance

Valuable tool in chemical synthesis processes

Upstream product

• 58164-14-0 1-bromo-2-amino-4-tert-butylbenzene 
• 70729-05-4 1-Bromo-4-tert-butyl-2-nitro-benzene 
• 3972-65-4 1-bromo-4-tert-butylbenzene 

Downstream Products

• 1597601-99-4 {[2-(4-tertbutyl-2-fluorophenyl)-5-nitrophenyl](phenyl)methylidene}(hexyl)amine 
• 1597602-03-3 3-tertbutyl-5-(cyclohexylmethyl)-6-phenyl-8-nitrophenanthridinium chloride 
• 1597601-93-8 potassium 2-fluoro-4-tertbutylphenyltrifluoroboronate 
• 1597601-98-3 2-(2-fluoro-4-tertbutylphenyl)-5-nitrobenzophenone 
• 1597602-47-5 C₃₀H₃₃FN₂O₂ 

Relevant academic research and scientific papers

Expanding the palette of phenanthridinium cations

5,6-Disubstituted phenanthridinium cations have a range of redox, fluorescence and biological properties. Some properties rely on phenanthridiniums intercalating into DNA, but the use of these cations as exomarkers for the reactive oxygen species (ROS), superoxide, and as inhibitors of acetylcholine esterase (AChE) do not require intercalation. A versatile modular synthesis of 5,6-disubstituted phenanthridiniums that introduces diversity by Suzuki-Miyaura coupling, imine formation and microwave-assisted cyclisation is presented. Computational modelling at the density functional theory (DFT) level reveals that the novel displacement of the aryl halide by an acyclic N-alkylimine proceeds by an SNAr mechanism rather than electrocyclisation. It is found that the displacement of halide is concerted and there is no stable Meisenheimer intermediate, provided the calculations consistently use a polarisable solvent model and a diffuse basis set.