58755-70-7

Usage

Uses

Used in Organic Synthesis:
4-Iodo-3-nitroanisole is utilized as a reagent in organic synthesis for its ability to contribute to the formation of various complex organic molecules. Its unique structure allows it to participate in a range of chemical reactions, facilitating the creation of new compounds with specific properties.
Used in Pharmaceutical Research:
In pharmaceutical research, 4-Iodo-3-nitroanisole serves as a valuable intermediate or building block for the development of new drugs. Its presence in the synthesis process can lead to the discovery of novel therapeutic agents with improved efficacy and selectivity.
Used in the Production of Pharmaceuticals:
4-Iodo-3-nitroanisole is employed in the manufacturing process of certain pharmaceuticals, where its chemical properties contribute to the desired medicinal attributes of the final product. Its role in this context is crucial for the synthesis of active pharmaceutical ingredients.
Used in the Production of Agrochemicals:
Similarly, in the agrochemical industry, 4-Iodo-3-nitroanisole is used in the synthesis of various compounds that have applications in agriculture, such as pesticides and herbicides. Its contribution to these products can enhance their effectiveness in controlling pests and weeds, thereby supporting crop protection and yield.

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

Upstream product

• 555-03-3 3-nitroanisole 
• 96-96-8 4-methoxy-2-nitroaniline 
• 7553-56-2 iodine 
• 7697-37-2 nitric acid 
• 77287-58-2 2-iodo-5-methoxybenzaldehyde 
• 33844-21-2 2-nitro-4-methoxybenzoic acid 
• 7757-83-7 sodium sulfite 

Downstream Products

• 760192-05-0 (4-methoxy-2-nitro-phenyl)-(2'-nitrophenyl)-amine 
• 857784-25-9 bis(4-methoxy-2-nitrophenyl)amine 
• 58755-67-2 2-(4-methoxy-2-nitrophenylsulfanyl)benzoic acid 
• 75753-19-4 4,4'-dimethoxy-2,2'-dinitrobiphenyl 
• 443303-81-9 4'-methoxy-2′-nitro-4,5-dihydro-[1,1'-biphenyl]-2(3H)-one 
• 889134-71-8 1,2,3-trimethoxy-5-(2-(4-methoxy-2-nitrophenyl)ethynyl)benzene 
• 912284-77-6 2-[(2-amino-4-methoxy-phenyl)-methyl-amino]-ethanol 
• 119880-01-2 (+/-)-N-(phenylsulfonyl)-1,2,7,7a-tetrahydrocycloprop<1,2-c>indol-4-one 
• 153898-57-8 N-(2-Iodo-5-methoxy-phenyl)-benzenesulfonamide 
• 153898-58-9 1-Benzenesulfonyl-6-methoxy-3-methylene-2,3-dihydro-1H-indole 
• 153898-64-7 N-Allyl-N-(2-iodo-5-methoxy-phenyl)-benzenesulfonamide 
• 153898-60-3 1-Benzenesulfonyl-3-iodomethyl-2,3-dihydro-1H-indol-6-ol 
• 115875-99-5 (1-Benzenesulfonyl-6-methoxy-2,3-dihydro-1H-indol-3-yl)-methanol 
• 153898-59-0 1-Benzenesulfonyl-3-iodomethyl-6-methoxy-2,3-dihydro-1H-indole 

Relevant academic research and scientific papers

Base-Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines

The current protocol represents a transition metal-free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2-iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a C?N bond formation followed by a radical C?C coupling in a cascade sequence. The used base potassium tert-butoxide plays a dual role in dehydrogenation and homolytic aromatic substitution reaction. Using this methodology, twenty substituted phenanthridine derivatives were synthesized with up to 85% isolated yield. (Figure presented.).

Inexpensive NaX (X = I, Br, Cl) as a halogen donor in the practical Ag/Cu-mediated decarboxylative halogenation of aryl carboxylic acids under aerobic conditions

Versatile and practical Ag/Cu-mediated decarboxylative halogenation between readily available aryl carboxylic acids and abundant NaX (X = I, Br, Cl) has been achieved under aerobic conditions in moderate to good yields. The halodecarboxylation is shown to be an effective strategy for S-containing heteroaromatic carboxylic acid and benzoic acids with nitro, chloro and methoxyl substituents at the ortho position. A gram-scale reaction and a three-step procedure to synthesize iniparib have been performed to evaluate the practicality of this protocol. A preliminary mechanistic investigation indicates that Cu plays a vital role and a radical pathway is involved in the transformation.

Discovery of Marinoquinolines as Potent and Fast-Acting Plasmodium falciparum Inhibitors with in Vivo Activity

We report the discovery of marinoquinoline (3H-pyrrolo[2,3-c]quinoline) derivatives as new chemotypes with antiplasmodial activity. We evaluated their inhibitory activities against P. falciparum and conducted a structure-activity relationship study, focusing on improving their potency and maintaining low cytotoxicity. Next, we devised quantitative structure-activity relationship (QSAR) models, which we prospectively validated, to discover new analogues with enhanced potency. The most potent compound, 50 (IC503d7 = 39 nM; IC50K1 = 41 nM), is a fast-acting inhibitor with dual-stage (blood and liver) activity. The compound showed considerable selectivity (SI > 6410), an additive effect when administered in combination with artesunate, excellent tolerability in mice (all mice survived after an oral treatment with a 1000 mg/kg dose), and oral efficacy at 50 mg/kg in a mouse model of P. berghei malaria (62% reduction in parasitemia on day 5 postinfection); thus, compound 50 was considered a lead compound for the discovery of new antimalarial agents.

Synthetic method of aryl halide taking aryl carboxylic acid as raw material

A synthetic method of an aryl halide taking aryl carboxylic acid as a raw material is characterized in that a corresponding aryl halide is formed by carrying out substitution reaction on an aryl carboxylic acid compound and haloid salt MX in an organic solvent under the condition that oxygen, a silver catalyst, a copper additive and a bidentate nitrogen ligand exist, wherein M in MX represents alkali metal or alkaline earth metal, and X represents F, Cl, Br or I. Compared with a conventional aryl halide synthetic method, the synthetic method disclosed by the invention has the obvious advantages that reaction raw materials (comprising aryl carboxylic acid and MX) are cheap and easy to obtain, the using amount of a metal catalyst is small, pollution to the environment when the oxygen is used as an oxidant is the smallest, good tolerance to various functional groups on an aromatic ring is obtained, the yield is high, and the like. The synthetic method disclosed by the invention can be widely applied to synthesis in the fields of medicine, materials, natural products and the like in industry and academia.

A new regiospecific synthesis method of 1H-pyrazolo[3,4-b]quinoxalines – Potential materials for organic optoelectronic devices, and a revision of an old scheme

A series of 6-substituted-1,3-diphenyl-1H-pyrazolo[3,4-b]quinoxalines were prepared using a new synthetic pathway: reductive cyclization of appropriate 5-(o-nitrophenyl)-pyrazoles with ferrous oxalate or triphenylphosphine. The main advantage of this procedure is that, contrary to the older protocols of pyrazolo[3,4-b]quinoxaline synthesis, this method allows for a substituent to be introduced to the carbocyclic ring without the formation of isomers. The pyrazole ring can also be modified to some extent. Furthermore, we propose a new mechanism for the oldest reported pyrazolo[3,4-b]quinoxaline synthesis, based on the condensation between o-phenylenediamine and 3,4-pyrazolin-5-diones.

Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions

Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu(I) as promoter and electron-rich ones by employing Pd(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (-I, Br, and Cl) through the decarboxylative functionalization of benzoic acids with readily available halogen sources CuX (X = I, Br, Cl), and easy preparation of benzonitriles from decarboxylative cyanation of aryl carboxylic acids with nontoxic and low-cost K4Fe(CN)6 under an oxygen atmosphere for the first time.

Synthetic method of N-((2-(1,3-dioxo-dihydroisoindol-2-yl)-propionyl)-5-methoxy)formamide

The invention discloses a synthetic method of N-(2-(1,3-dioxo-dioxoisoindolin-2-yl)-propionyl)-5-methoxy)formamide. 2-nitro-4-anisidine is taken as an initial raw material, 2-iodine-3-methoxy nitrobenzene is obtained by substitution reaction on a diazonium salt aromatic ring, and then the 2-iodine-3-methoxy nitrobenzene and propargylamine are subjected to Castro-Stephens coupling reaction, reduction reaction and acylation reaction to obtain the N-(2-(1,3-dihydroisoindol-2-yl)-propionyl)-5-methoxy)formamide. Reaction conditions are optimized based on the prior art, and concentrated sulfuric acid replaces concentrated nitric acid; manganese dioxide solid is adopted to catalyze the reaction of propargyl bromide and phthalimide kali salt; manganous-manganic oxide is adopted as a catalyst to catalyze and promote the reaction together with triethylamine, bispalladium chloride and cuprous iodide, the reaction efficiency and yield of a final product are improved, and the industrial production and promotion of the N-(2-(1,3-dioxo-dihydroisoindol-2-yl)-propionyl)-5-methoxy)formamide are facilitated.

Synthesis of Unexpected trans-meso Macrocycle from Novel Unsymmetrical Tetraphenylene

A highly unsymmetrical trisubstituted tetraphenylene was designed and synthesized as a novel superamolecular scaffold for an unexpected trans-meso tetraphenylene macrocycle, whose structure was unequivocally characterized by an X-ray crystallographic anal

Using Anilines as Masked Cross-Coupling Partners: Design of a Telescoped Three-Step Flow Diazotization, Iododediazotization, Cross-Coupling Process

The conversion of commercially available anilines into biaryl and biarylacetylene products was realized by using a telescoped, three-reactor flow diazotization/iododediazotization/cross-coupling process. The segmented flow stream created by off-gassing during the Sandmeyer sequence was restored to a continuous column of reaction solution by using a specially designed continuous-flow unit controlled by custom software created in-house. The resultant aryl iodide was then combined with a stream of cross-coupling solution that fed into the final reactor. The system proved versatile as modifications to the diazotization/iododediazotization sequence could be made rapidly to account for any substrate specificity (e.g., solubility problems), leading to a wide substrate scope of Suzuki–Miyaura and Sonogashira cross-coupled products.

Halogenation and DNA cleavage via thermally stable arenediazonium camphorsulfonate salts

A series of stable arenediazonium camphorsulfonate salts (2a-2j) were synthesized by simple diazotization of several aromatic amines in the presence of sodium nitrite and camphorsulfonic acid. All the new arenediazonium camphorsulfonates, which were characterized by multinuclear (1H and 13C) NMR, IR, DSC, and X-ray diffraction analysis (2e and 2f) provide unambiguous proof for the molecular structures of 2e and 2f. The efficient application of these salts in halogenation reactions was studied in solvent and solvent-free conditions and the DNA cleavage activity was also assessed. These arenediazonium camphorsulfonate salts are noticed as efficient DNA cleaving agents.