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Usage

Uses

Used in Pharmaceutical Synthesis:
5-Iodo-2-nitrophenol is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with specific therapeutic properties.
Used in Dye Production:
In the dye industry, 5-Iodo-2-nitrophenol is used as a starting material for the production of various dyes, capitalizing on its chemical structure to create a range of colorants for different applications.
Used in Pesticide Manufacturing:
5-Iodo-2-nitrophenol is utilized in the manufacturing of pesticides, where its chemical properties provide effective pest control solutions for agricultural and other industries.
Used as a Reagent in Organic Chemistry:
As a reagent, 5-Iodo-2-nitrophenol is employed in various organic chemistry reactions, facilitating important transformations and processes in chemical research and development.
Used in Research for Cell Signaling Pathways:
5-Iodo-2-nitrophenol is used as a potent inhibitor of tyrosine kinase enzymes in research settings, making it a valuable tool for studying and understanding the complexities of cell signaling pathways, which is crucial for advancing knowledge in cellular and molecular biology.
Environmental Considerations:
Given its status as a known pollutant, the use and disposal of 5-Iodo-2-nitrophenol are regulated in some regions to minimize its impact on aquatic organisms and the environment at large. This highlights the need for responsible handling and management of this chemical compound in industrial applications.

Upstream product

• 626-02-8 3-Iodophenol 
• 636-98-6 p-nitrobenzene iodide 
• 7664-93-9 sulfuric acid 
• 873388-13-7 (5-iodo-2-nitro-phenyl)-arsonic acid 

Downstream Products

• 860585-81-5 2-methoxy-4-iodonitrobenzene 
• 616-74-0 4,6-dinitroresorcinol 
• 680214-26-0 bis-(3-methoxy-4-nitro-phenyl)-disulfide 
• 53398-97-3 5-iodo-2,4-dinitro-phenol 
• 99968-80-6 5-iodo-2-aminophenol 
• 4840-88-4 3-iodo-2,4,6-trinitro-phenol 
• 941594-27-0 5-[2-benzyloxy-4-(4-ethylpyridin-2-ylmethyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanyl-ethyl)-1,2,5-thiadiazolidin-3-one 
• 1132677-86-1 5-(4-benzyl-2-benzyloxyphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one 
• 941594-26-9 5-(2-benzyloxy-4-iodomethylphenyl)-1,1-dioxo-2-(2-trimethylsilanyl-ethyl)-1,2,5-thiadiazolidin-3-one 
• 941594-25-8 5-(2-benzyloxy-4-hydroxymethylphenyl)-1,1-dioxo-2-(2-trimethylsilanyl-ethyl)-1,2,5-thiadiazolidin-3-one 
• 941594-23-6 3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanyl-ethyl)-1,2,5-thiadiazolidin-2-yl]-benzaldehyde 
• 1132677-90-7 5-(4-benzyl-2-benzyloxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one 
• 1233374-58-7 5-[4-(3-aminopropyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one trifluoroacetate 
• 1057340-40-5 (3-(3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl)-propyl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Protein-specific localization of a rhodamine-based calcium-sensor in living cells

A small synthetic calcium sensor that can be site-specifically coupled to proteins in living cells by utilizing the bio-orthogonal HaloTag labeling strategy is presented. We synthesized an iodo-derivatized BAPTA chelator with a tetramethyl rhodamine fluorophore that allows further modification by Sonogashira cross-coupling. The presented calcium sensitive dye shows a 200-fold increase in fluorescence upon calcium binding. The derivatization with an aliphatic linker bearing a terminal haloalkane-function by Sonogashira cross-coupling allows the localization of the calcium sensor to Halo fusion proteins which we successfully demonstrate in in vitro and in vivo experiments. The herein reported highly sensitive tetramethyl rhodamine based calcium indicator, which can be selectively localized to proteins, is a powerful tool to determine changes in calcium levels inside living cells with spatiotemporal resolution.

Antileishmanial bis-arylimidamides: DB766 analogs modified in the linker region and bis-arylimidamide structure-activity relationships

Analogs of the lead antileishmanial bis-arylimidamide DB766 were prepared that possess unsymmetrical substitutions on the diphenylfuran linker, and an additional compound was synthesized that contains isopropoxy groups meta to the central furan. These agents all displayed nanomolar in vitro potency against intracellular Leishmania with selectivity indexes >100 compared to J774 macrophages. While the unsymmetrical analogs were toxic to mice when given ip at 30 mg/kg/day, the compound bearing the meta isopropoxy groups was well tolerated by mice and showed activity in a murine model of visceral leishmaniasis when administered ip at 30 mg/kg/day for five days.

A Pd[0]-catalyzed Ullmann cross-coupling/reductive cyclization approach to C-3 mono-alkylated oxindoles and related compounds

The Pd[0]-catalyzed Ullmann cross-coupling of o-nitrohaloarenes 1a-e with the brominated heterocycles 2a-f delivers the expected products 3a-j in good to excellent yields. The reductive cyclization of such products, as well as N-acyl derivatives 3k, l, and m, has been investigated and provided the C-3 mono-substituted oxindoles 5a-d, f, g, k, and m, the direct reduction products 4i and j or indole 5l.

Geldanamycin derivative inhibition of HGF/SF-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation

Ansamycins, including geldanamycin and the derivative 17-allylamino-17- demethoxygeldanamycin, and radicicol are known for their ability to tightly bind to the ATP-binding site of the amino-terminal domain region of heat shock protein 90. We have found that geldanamycin and some of its derivatives can inhibit hepatocyte growth factor/scatter factor-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation at femtomolar levels. Assessment is made of structural requirements for such an activity and evidence is given that distinguishes the target of such an activity from that of heat shock protein 90.

GELDANAMYCIN AND DERIVATIVES INHIBIT CANCER INVASION AND IDENTIFY NOVEL TARGETS

Geldanamycin derivatives that block the uPA-plasmin network and inhibit growth and invasion by glioblastoma cells and other tumors at femtomolar concentrations are potentially highly active anti-cancer drugs. GA and various 17-amino-17-demethoxygelddanamycin derivatives are disclosed that block HGF/SF-mediated Met tyrosine kinase receptor-dependent uPA activation at fM levels. Other ansamycins (macbecins I and II), GA derivatives, and radicicol required concentrations several logs higher (≥nM) to achieve such inhibition. The inhibitory activity of tested compounds was discordant with the known ability of drugs of this class to bind to hsp90, indicating the existence of a novel target(s) for HGF/SF -mediated events in tumor development. Methods of using such compounds to inhibit cancer cell activities and to treat tumors are disclosed. Such treatment with low doses of these highly active compounds provide an option for treating various Met-expressing tumors, in particular invasive brain cancers, either alone or in combination with conventional surgery, chemotherapy, or radiotherapy.

Hydroxylation of Nitroarenes with Alkyl Hydroperoxide Anions via Vicarious Nucleophilic Substitution of Hydrogen

Rhone-Poulenc Polska Ltd., ul. Grzybowska 80/82, 00-844 Warszawa, Poland Garbo- and heterocyclic nitroarenes react with anions of tert-butyl and cumyl hydroperoxides in the presence of strong bases to form substituted o- and p-nitrophenols. The reaction usually proceeds in high yields and is of practical value as a method of synthesis and manufacturing of nitrophenols. Orientation of the hydroxylation can be controlled to a substantial extent by selection of the proper conditions. Basic mechanistic features of this process were clarified.