5399-03-1

Basic information

• Product Name: 2-Iodo-4-nitroanisole
• Synonyms: 2-IODO-4-NITROANISOLE;2-Iodo-4-nitroanisol;Benzene, 2-iodo-1-methoxy-4-nitro-;2-IODO-1-METHOXY-4-NITROBENZENE;2-Iodo-4-ntiroanisole;1-Iodo-2-Methoxy-5-nitrobenzene;2-Iodo-1-methoxy-4-nitrobenzene, 2-Iodo-4-nitrophenyl methyl ether;3-Iodo-4-Methoxynitrobenzene[2-Iodo-4-nitroanisole]
• CAS NO: 5399-03-1
• Molecular Formula: C₇H₆INO₃
• Molecular Weight: 279.03
• EINECS: 1592732-453-0
• Product Categories: Aromatic Ethers;Anisoles, Alkyloxy Compounds & Phenylacetates;Iodine Compounds;Nitro Compounds
• Mol File: 5399-03-1.mol

Chemical Properties

• Melting Point: 96-98°C
• Boiling Point: 343.3 °C at 760 mmHg
• Flash Point: 161.4 °C
• Appearance: /
• Density: 1.893 g/cm³
• Vapor Pressure: 0.000141mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: Room temperature.
• CAS DataBase Reference: 2-Iodo-4-nitroanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodo-4-nitroanisole(5399-03-1)
• EPA Substance Registry System: 2-Iodo-4-nitroanisole(5399-03-1)

Safety Data

• Hazardous Substances Data: 5399-03-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Iodo-4-nitroanisole is used as a synthetic intermediate for the production of pharmaceuticals. Its reactivity allows for the creation of complex molecules that can be further utilized in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Iodo-4-nitroanisole serves as a building block in the synthesis of agrochemicals, contributing to the development of pesticides and other agricultural chemicals that enhance crop protection and yield.
Used in Dye Industry:
2-Iodo-4-nitroanisole is utilized as a precursor in the dye industry, where it is involved in the synthesis of various dyes used in coloring textiles, plastics, and other materials.
Used in Organic Synthesis:
As a reagent in organic synthesis, 2-Iodo-4-nitroanisole is employed for the production of other organic compounds. Its ability to undergo multiple chemical transformations makes it a key component in the synthesis of a wide range of organic molecules.
It is important to handle 2-Iodo-4-nitroanisole with care due to its potential health and environmental hazards, ensuring proper safety measures are in place during its use in various applications.

InChI:InChI=1/C7H6INO3/c1-12-7-3-2-5(9(10)11)4-6(7)8/h2-4H,1H3

Upstream product

• 529-28-2 4-iodoanisol 
• 100-17-4 para-methoxynitrobenzene 
• 696-62-8 para-iodoanisole 
• 28896-47-1 2,4-diiodoanisole 
• 89487-91-2 2-iodo-4-nitrophenol 
• 99-59-2 3-amino-4-methoxynitrobenzene 
• 7553-56-2 iodine 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 533-58-4 2-Iodophenol 
• 139-02-6 sodium phenoxide 
• 90-04-0 2-methoxy-phenylamine 
• 91-23-6 2-Nitroanisole 
• 52692-09-8 4-iodo-2-nitroanisole 

Downstream Products

• 74587-12-5 3-iodo-4-methoxyaniline 
• 81763-59-9 2,2'-dimethoxy-5,5'-dinitrobiphenyl 
• 90584-85-3 4-nitro-2-(1-pentynyl)anisole 
• 261173-06-2 3-iodo-4-methoxyaniline hydrochloride 
• 846023-57-2 4-(2-methoxy-5-nitrophenyl)-2-furaldehyde 
• 10496-75-0 2-methoxy-5-nitrobenzylnitrile 
• 82504-06-1 3-iodo-4-methoxybenzonitrile 
• 168267-11-6 2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzaldehyde 
• 168266-51-1 Vofopitant dihydrochloride 
• 261173-10-8 2,2,2-trifluoro-N-(3-iodo-4-methoxyphenyl)acetamide 
• 261173-18-6 2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzonitrile 
• 261173-12-0 1-(3-iodo-4-methoxyphenyl)-5-(trifluoromethyl)-1H-tetrazole 
• 28896-47-1 2,4-diiodoanisole 
• 144280-50-2 2,8-dinitrodibenzofuran 

Relevant articles and documents

3-substituted-N-(4-hydroxynaphthalen-1-yl)arylsulfonamides as a novel class of selective Mcl-1 inhibitors: Structure-based design, synthesis, SAR, and biological evaluation

Mcl-1, an antiapoptotic member of the Bcl-2 family of proteins, is a validated and attractive target for cancer therapy. Overexpression of Mcl-1 in many cancers results in disease progression and resistance to current chemotherapeutics. Utilizing high-throughput screening, compound 1 was identified as a selective Mcl-1 inhibitor and its binding to the BH3 binding groove of Mcl-1 was confirmed by several different, but complementary, biochemical and biophysical assays. Guided by structure-based drug design and supported by NMR experiments, comprehensive SAR studies were undertaken and a potent and selective inhibitor, compound 21, was designed which binds to Mcl-1 with a Ki of 180 nM. Biological characterization of 21 showed that it disrupts the interaction of endogenous Mcl-1 and biotinylated Noxa-BH3 peptide, causes cell death through a Bak/Bax-dependent mechanism, and selectively sensitizes Eμ-myc lymphomas overexpressing Mcl-1, but not Eμ-myc lymphoma cells overexpressing Bcl-2. Treatment of human leukemic cell lines with compound 21 resulted in cell death through activation of caspase-3 and induction of apoptosis.

SMALL MOLECULE INHIBITORS OF MCL-1 AND USES THEREOF

This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having sulfonamido-1-hydroxynaphthalene structure which function as inhibitors of Mcl-1 protein, and their use as therapeutics for the treatment of cancer and other diseases.

Environmental friendly method for the iodination of moderately active arenes

An effective and environmental friendly method for the iodination of various moderately active methoxy arenes, phenols and anilines using hydrogen peroxide and acidified sodium periodate in aqueous ethanol medium is reported. The extent of iodination is e

MACROCYCLIC COMPOUNDS AND THEIR USE AS KINASE INHIBITORS

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Oxidative iodination of deactivated arenes in concentrated sulfuric acid with I2/NaIO4 and KI/NaIO4 iodinating systems

Deactivated arenes were mono- or diiodinated with strong electrophilic I+ reagents, which were prepared from NaIO4 and either I2 or KI in concentrated H2SO4 (minimum 95% by weight). In general a small excess of the dark brown iodinating solution was used (1.1/1.5 equivalents, for nitrobenzene two equivalents was required). The iodinations were conducted at 25-30 °C with a reaction time of 1-2 hours using either a 'direct' or an 'inverse' method of aromatic iodination to give mono- or diiodinated pure products in 31-91% optimized yields. Georg Thieme Verlag Stuttgart.

Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylisulfonium halides generated in situ

Halodimethylsulfonium halide 1, which is readily formed in situ from hydrohaloic acid and DMSO, is a good nucleophilic halide. This activated nucleophilic halide rapidly converts aryldiazonium salt prepared in situ by the same hydrohaloic acid and nitrite ion to aryl chlorides, bromides, or iodides in good yield. The combined action of nitrite ion and hydrohaloic acid in DMSO is required for the direct transformation of aromatic amines, which results in the production of aryl halides within 1 h. Substituted compounds with electron-donating or -withdrawing groups or sterically hindered aromatic amines are also smoothly transformed to the corresponding aromatic halides. The only observed by-product is the deaminated arene (usually 7%). The isolated aryldiazonium salts can also be converted to the corresponding aryl halides using 1. The present method offers a facile, one-step procedure for transforming aminoarenes to haloarenes and lacks the environmental pollutants that usually accompany the Sandmeyer reaction using copper halides.

Eco-friendly oxidative iodination of various arenes with sodium percarbonate as the oxidant http://www.mdpi.org

Six easy laboratory procedures are presented for the oxidative iodination of various aromatics, mostly arenes, with either molecular iodine or potassium iodide (used as the sources of iodinating species, I+ or I 3+), in the presence of sodium percarbonate (SPC), a stable, cheap, easy to handle, and eco-friendly commercial oxidant.

An aromatic iodination method, with iodic acid used as the only iodinating reagent

Benzene, halobenzenes, and a number of more or less deactivated arenes, including nitrobenzene, readily reacted in anhydrous HIO3/AcOH/ Ac2O/conc. H2SO4 mixtures to probably give ArIO2 intermediates or other hypervalent species (not isolated). The final reaction mixtures were poured into excess aq. Na2SO3 solution (a reductant) to give the purified iodinated products in 39-83% yields.

Easy, inexpensive and effective oxidative iodination of deactivated arenes in sulfuric acid

Two 'model' deactivated arenes, benzoic acid and nitrobenzene, were effectively monoiodinated within 1 h at 25-30 °C, with strongly electrophilic I+ reagents, prior prepared from diiodine and various oxidants (CrO3, KMnO4, active MnO2, HIO 3, NaIO3, or NaIO4) in 90% (v/v) concd sulfuric acid (ca. 75 mol% H2SO4). Next, an I2/ NaIO3/90% (v/v) concd H2SO4 exemplary system was used to effectively mono- or diiodinate a number of deactivated arenes. All former papers dealing with the direct iodination of deactivated arenes are briefly reviewed.

Eco-friendly Oxidative Iodination of Various Arenes with a Urea-Hydrogen Peroxide Adduct (UHP) as the Oxidant

Three easy eco-friendly laboratory procedures are presented for the oxidative iodination of various activated and deactivated arenes with molecular iodine, in the presence of UHP (percarbamide), a stable, strongly H-bonded, solid urea-hydrogen peroxide adduct as the oxidant.