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
• Article Data: 16

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

General Description

2-Iodo-4-nitroanisole is a chemical compound with the molecular formula C7H6INO3. It is a pale yellow solid that is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and dyes. The compound is primarily used in organic synthesis as a building block for creating complex molecules, and it is known for its high reactivity and ability to undergo various chemical transformations. 2-Iodo-4-nitroanisole is also used as a reagent in the production of other organic compounds, and it is important to handle it with caution due to its potential health and environmental hazards.

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

Upstream product

• 696-62-8 para-iodoanisole 
• 28896-47-1 2,4-diiodoanisole 
• 529-28-2 4-iodoanisol 
• 64-19-7 acetic acid 
• 77770-09-3 3-amino-4-methyloxyphenyliodide 
• 52692-09-8 4-iodo-2-nitroanisole 
• 91-23-6 2-Nitroanisole 
• 90-04-0 2-methoxy-phenylamine 
• 139-02-6 sodium phenoxide 
• 533-58-4 2-Iodophenol 
• 7697-37-2 nitric acid 
• 100-17-4 para-methoxynitrobenzene 
• 7553-56-2 iodine 
• 99-59-2 3-amino-4-methoxynitrobenzene 

Downstream Products

• 74587-12-5 3-iodo-4-methoxyaniline 
• 81763-59-9 2,2'-dimethoxy-5,5'-dinitrobiphenyl 
• 876343-45-2 5-(2-methoxy-5-nitrophenyl)thiazole 

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.

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

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.