105752-04-3

Usage

Uses

Used in Organic Synthesis:
4-IODO-3-NITROANILINE is used as a chemical intermediate in the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable component in the development of new chemical entities and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-IODO-3-NITROANILINE is used as a building block for the synthesis of active pharmaceutical ingredients (APIs). Its presence in the molecular structure can impart specific biological activities and properties to the final drug product, contributing to its therapeutic effects.
Used in Dye and Pigment Industry:
4-IODO-3-NITROANILINE, due to its yellowish-orange color, can be utilized as a dye or pigment in various applications, such as coloring textiles, plastics, and other materials. Its chemical properties allow for stable coloration and resistance to fading.
Used in Research and Development:
4-IODO-3-NITROANILINE serves as a valuable research tool in the field of organic chemistry, enabling scientists to explore new reaction pathways, investigate the effects of structural modifications on chemical and biological properties, and develop novel synthetic methodologies.

InChI:InChI=1/C6H5IN2O2/c7-5-2-1-4(8)3-6(5)9(10)11/h1-3H,8H2

Upstream product

• 99-09-2 3-nitro-aniline 
• 7647-01-0 hydrogenchloride 
• 540-37-4 p-aminoiodobenzene 
• 709-49-9 1-iodo-2,4-dinitrobenzene 

Downstream Products

• 609-73-4 o-nitroiodobenzene 
• 89488-57-3 1,4-diiodo-2-nitrobenzene 
• 116529-47-6 2,4-diiodo-5-nitro-aniline 
• 146512-89-2 2,4-diiodo-3-nitroaniline 
• 1329166-65-5 methyl 4-iodo-3-nitrophenylcarbamate 
• 116779-70-5 1,2,4-triiodo-3-nitro-benzene 
• 116529-50-1 2,3,6-triiodo-aniline 
• 861609-61-2 2,4,5-triiodo-aniline 
• 861606-52-2 1,3-diiodo-2-nitro-benzene 
• 634-68-4 1,2,3,4-tetraiodobenzene 
• 116779-71-6 1,2,4-triiodo-5-nitro-benzene 
• 615-68-9 1,2,4-triiodobenzene 
• 861523-55-9 acetic acid-(4-iodo-3-nitro-anilide) 

Relevant academic research and scientific papers

Redox-dependent conformational switching of diphenylacetylenes

Herein we describe the design and synthesis of a redox-dependent single-molecule switch. Appending a ferrocene unit to a diphenylacetylene scaffold gives a redox-sensitive handle, which undergoes reversible one-electron oxidation, as demonstrated by cyclic voltammetry analysis. 1H-NMR spectroscopy of the partially oxidized switch and control compounds suggests that oxidation to the ferrocenium cation induces a change in hydrogen bonding interactions that results in a conformational switch.

Greener iodination of arenes using sulphated ceria-zirconia catalysts in polyethylene glycol

An environmentally benign method for the selective monoiodination of diverse aromatic compounds has been developed using reusable sulphated ceria-zirconia under mild conditions. The protocol provides moderate to good yields and selectively introduces iodine at the para/ortho position in monosubstituted arenes. SO42-/Ce0.07Zr 0.93O2 was found to be the best choice for the synthesis of aryl iodides in high yield, presumably due to the maximum number of acid sites (4.23 mmol g-1) among the various compositions of the catalyst system.

Synthesis, molecular and photovoltaic properties of an indolo[3,2-b]indole- based acceptor-donor-acceptor small molecule

Indolo[3,2-b]indole, containing two fused indole units, is an unexplored but promising electron-rich molecule for constructing donor-acceptor materials due to its planar, symmetric, and extended conjugated structure. We have successfully developed a new synthetic pathway to prepare 2,7-diboronic ester-indolo[3,2-b]indole, which was then reacted with dithienodiketopyrrolo- pyrrole acceptor to afford a new acceptor-donor-acceptor (A-D-A) conjugated molecule, 2,7-bis(dithienodiketopyrrolo-pyrrole)indolo[3,2-b]indole (2,7-DPPIIDPP). II is used to stand for indolo[3,2-b]indole in order to emphasize that this compound is constructed from two indole units. The A-D-A linkage through the 2,7-positions of II not only preserves the phenylene units in the para-conjugation but also renders stronger electron-donating strength. This material exhibited good thermal stability, high crystallinity, and broad UV/Vis absorption. The solution-processed bulk heterojunction device using the configuration of ITO/PEDOT:PSS/2,7-DPPIIDPP:PC71BM/Ca/Al exhibited a Voc of 0.72 V, a Jsc of 6.88 mA/cm2, and an FF of 49.6 %, leading to a power conversion efficiency (PCE) of 2.45 %. A new acceptor-donor-acceptor conjugated molecule, 2,7-bis(dithienodiketopyrrolo- pyrrole)indolo[3,2-b]indole (2,7-DPPIIDPP) was designed and synthesized. This material exhibited good thermal stability, high crystallinity, and broad UV/Vis absorption. The solution-processed bulk heterojunction device using the configuration of ITO/PEDOT:PSS/ 2,7-DPPIIDPP:PC71BM/Ca/Al was characterized. Copyright

A novel ternary approach to quantitatively assess the reactivity of nitroaniline regioisomers by investigation of rapid iodination kinetics using hydrodynamic voltammetry, reduction propensities from polarography, and binding affinities from molecular docking simulations

A novel ternary approach to assess the reactivity of nitroaniline regioisomers on a quantitative scaffold has been manifested on the basis of three complementary tenets: kinetics, polarography, and molecular docking. Data from investigation of rapid iodination kinetics of nitroaniline regioisomers by hydrodynamic voltammetry in aqueous medium, reduction propensities of these regioisomers from polarography, and their binding affinities with hypoxanthine-guanine phophoribosyltransferase (HPRT1) from molecular docking simulations lead to inferences regarding their reactivity that agree in entirety. The experimentally determined magnitudes of the specific reaction rates, energies of activation, collision frequencies, entropies of activation from kinetic studies, and reduction propensities of nitroaniline regioisomers from polarograms when complemented with in silico binding energies of these regioisomer ligands with the receptor enzyme, assess their relative reactivities in unison on a quantitative scaffold. This novel ternary approach unambiguously assesses the reactivity of the regioisomers of nitroaniline as 4-nitroaniline?>?2-nitroaniline?>?3-nitroaniline.

Unpicking the determinants of amide NH?OC hydrogen bond strength with diphenylacetylene molecular balances

Hydrogen bonding plays an essential part in dictating the properties of natural and synthetic materials. Secondary amides are well suited to cross-strand interactions through the display of both hydrogen bond donors and acceptors and are prevalent in poly

Compound, organic light-emitting device including the same and flat display apparatus

A compound, an organic light-emitting device, and a flat display apparatus, the compound being represented by any one selected from the following Formula 1, Formula 2, and Formula 3 as described in the description.

Remarkable switch in the regiochemistry of the iodination of anilines by N-iodosuccinimide: Synthesis of 1,2-dichloro-3,4-diiodobenzene

Direct iodination of anilines by NIS in polar solvents (such as DMSO) affords p-iodinated products with up to >99% regioselectivity. Switching to less polar solvents (such as benzene) in the presence of AcOH inverts this outcome toward dramatically increased or preferential generation of the o-isomers, also with up to >99% regioselectivity. This finding was exploited in the synthesis of 1,2-dichloro-3,4-diiodobenzene. Georg Thieme Verlag Stuttgart - New York.

A practical iodination of aromatic compounds by using iodine and iodic acid

This article describes simple and efficient method for the iodination of different aromatic amines, hydroxy aromatic aldehydes, hydroxy acetophenones and phenols using iodine and iodic acid in ethanol as a solvent. Notable advantages include mild reaction condition, no need of catalyst, short reaction time, simple practical procedure, giving excellent yield of the product. Copyright Taylor & Francis Group, LLC.

Effect of the electronic structure of the radical anions of 4-substituted 1,2-and 1,3-dinitrobenzenes on the regioselectivity of reduction of the nitro groups

Theoretical and experimental regularities of the regioselectivity of the reduction of one of the two nitro groups in unsymmetrical dinitrobenzenes were studied. It was found that the regioselectivity of the formation of isomeric nitroanilines depends on the structure of the substrate and the nature of the reducing agent. The reduction regioselectivity model was verified, according to which radical anion protonation is the major reaction direction. Pleiades Publishing, Inc. 2006.

Hydrogen bonding in substituted nitroanilines: hydrogen-bonded sheets in 4-iodo-3-nitroaniline

In the title compound, C6H5IN2O2, the nitro group is disordered over two sets of sites, each with 0.5 occupancy, and the amino N atom is pyramidal. The molecules are linked into sheets by a combination of three-centre N-H...(O)2 hydrogen bonds involving alternative pairs of O-atom sites and two-centre N-H...N hydrogen bonds involving the pyramidal amino group.