53663-23-3

Usage

Uses

Used in Organic Synthesis:
1,2,3-Triiodo-5-nitrobenzene is used as a reagent for introducing iodine atoms into organic molecules, which is crucial for the synthesis of various complex organic compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 1,2,3-triiodo-5-nitrobenzene is utilized in the development and manufacturing of certain drugs, contributing to the medicinal properties of these products.
Used in Dye Production:
1,2,3-triiodo-5-nitrobenzene is also employed in the production of dyes, capitalizing on its yellow color to create pigments for various applications.
It is important to handle and dispose of 1,2,3-triiodo-5-nitrobenzene with caution due to its toxic nature, ensuring the safety of human health and the environment.

Upstream product

• 98-95-3 nitrobenzene 
• 100-01-6 4-nitro-aniline 
• 636-98-6 p-nitrobenzene iodide 
• 5398-27-6 2,6-diiodo-4-nitroaniline 

Downstream Products

• 744215-77-8 1-(2,6-diiodo-4-nitro-phenoxy)-3-methoxy-benzene 
• 860734-40-3 1-(2,6-diiodo-4-nitro-phenylsulfanyl)-4-methoxy-benzene 
• 856060-74-7 (2,6-diiodo-4-nitro-phenyl)-p-tolyl sulfide 
• 744215-04-1 1-(2,6-diiodo-4-nitro-phenoxy)-2-methoxy-benzene 
• 123568-39-8 5-Nitro-1,2,3-tris-phenylethynyl-benzene 
• 123568-40-1 5-Nitro-1,2,3-tris-trimethylsilanylethynyl-benzene 
• 35122-96-4 3,5-diiodoaniline 
• 1596-67-4 O-(4-hydroxyphenyl)-3,5-diiodo-L-tyrosine 
• 68596-99-6 3,4,5-Triiodobenzenediazonium nitrate 
• 860532-33-8 4-[3,5-diiodo-4-(4-methoxy-phenoxy)-phenoxy]-3,5-diiodo-aniline 
• 855290-83-4 4-[3,5-diiodo-4-(4-methoxy-phenoxy)-phenoxy]-3,5-diiodo-benzonitrile 
• 860523-76-8 4-[3,5-diiodo-4-(4-methoxy-phenoxy)-phenoxy]-3,5-diiodo-benzaldehyde 

Relevant academic research and scientific papers

Directing the Self-Assembly Behaviour of Porphyrin-Based Supramolecular Systems

The self-assembly behaviour of a library of tetra-amidated porphyrin molecules decorated with a variety of solubilizing wedges is investigated as dilute solutions in methylcyclohexane. Small changes in the solubilising wedge of the porphyrins resulted in

Amphiphilic Fluorescence Resonance Energy-Transfer Dyes: Synthesis, Fluorescence, and Aggregation Behavior in Water

Amphiphilic pyrene/perylene bis-chromophore dyes were synthesized from unsymmetrically substituted perylene bisimide dyes, which were obtained through three synthetic methods. The optical and aggregation behaviors of these functional dyes were studied by means of UV/Vis absorption and fluorescence spectroscopy, dynamic light scattering, and TEM. These dyes are highly fluorescent and cover the whole visible-light region. A donor/acceptor dye displays intramolecular fluorescence resonance energy transfer (FRET), with a high efficiency of up to 96.4 percent from pyrene to perylene bisimide chromophores, which leads to a high fluorescence color sensitivity to environmental polarity. Under a λ=365 nm UV lamp, the light-emitting colors of the donor/acceptor dye change from green to yellow with increasing solvent polarity, which demonstrates application potential as a new class of FERT probes. The donor/acceptor dye in water was assembled into hollow vesicles with a narrow size distribution. The bilayer structure of the vesicular wall was directly observed by means of TEM. These vesicular aggregates in water are fluorescent at λ=650–850 nm within the near-infrared region.

Synthesis and optoelectronic properties of janus -dendrimer-type multivalent donor-acceptor systems

A convergent, multistep protocol was employed for the synthesis of a Janus-type multivalent donor-acceptor system. The synthetic approach is based on a Sonogashira cross-coupling of two differently ferrocene-(Fc) substituted dendrons and a final sixfold [

A mild and convenient synthesis of 1,2,3-triiodoarenes via consecutive iodination/diazotization/iodination strategy

A mild and convenient synthesis of 1,2,3-triiodoarenes has been developed. This method consists of two steps which can be performed on multigram scale with moderate to excellent yields. This report discloses a practical synthesis of 1,2,3-triiodoarenes and 1,2,3-trihaloarenes that is general in scope, operationally simple, scalable, and is easy to workup and to purify. We also report the first regioselective transmetalation reaction of 1,2,3-triiodoarenes to provide ortho-diiodoaryl derivatives, which are useful building blocks and indeed are hard to make by other means. CSIRO 2013.

Shape-Switchable Azo-Macrocycles

The synthesis of four shape-switchable macrocycles comprising different peripheral substituents is described. The macro- cycles 1-4 consist of m-terphenyl semicircles interlinked by two azo joints. These macrocycles were assembled from ni- tro-functionalized m-terphenyl moieties through reductive dimerization. The semicircles were assembled through Suzuki cross-coupling reactions. The molecular weights of the macrocycles were determined by vapour pressure osmome- try, because mass spectrometry failed in the cases of 2 and 3. The E - Z photoisomerization reactions were analysed by UV/Vis spectroscopy complemented by JH NMR studies. A very slow thermal back-reaction indicated considerable stabilization of the Z isomer. The reduced efficiency of the thermal back-reaction probably arises from the reduced degree of freedom due to the mechanical interlinking of the two azo groups. The photostationary state consisted of all-Z (85%) and all-E isomers (15 %). The E - Z transformation induced by irradiation displayed simple exponential kinetics, which indicates pairwise switching of the two azo groups in a macrocycle, at least on the timescale under investigation.

Morphology control of fluorescent nanoaggregates by co-self-assembly of wedge- and dumbbell-shaped amphophilic perylene bisimides

Wedge- and dumbbell-shaped amphiphilic perylene bisimides PBI 1-4 were synthesized. The wedge-shaped PBI 1 and PBI 2 and dumbbell-shaped PBI 4 self-assemble into micelles, and rod aggregates in aqueous solution, respectively. Interestingly, the co-self-assembly of wedge-shaped PBI 1 with dumbbell-shaped PBI 3 generates hollow vesicles with bilayer structures because of the curvature changes during the self-assembly process. The bilayer vesicles could be stabilized by in situ photopolymerization. Copyright

Iodination of nitroarenes by a superactive reagent based on iodine chloride

Iodine chloride reacts with Ag2SO4 in H2SO4 to give a new superelectrophilic reagent capable of iodinating nitrobenzene, halogenated nitrobenzenes, nitrotoluenes, and aromatic compounds with two nitro groups in the ring. Mononitroarenes are easily iodinated at 0-20 deg C, while dinitroarenes require heating to 100-170 deg C.

Direct Aromatic Periodination

Periodic acid and iodine in concentrated sulfuric acid exhaustively iodinated unactivated aromatic substrates.Thus benzene, nitrobenzene, benzoic acid, chlorobenzene, phthalic anhydride, and toluene were all converted to their periodo derivatives.Benzonitrile was converted to pentaiodobenzamide.This direct method compared favorably with the only general periodination procedure available, a mercuration/iododemercuration sequence.Partially iodinated products were obtained under less vigorous conditions.Thus, triiodo derivatives were obtained from nitrobenzene, benzo-ic acid, and toluene; tetraiodo derivatives were obtained from benzene, chlorobenzene, and trifluorobenzene.