75676-72-1

Usage

Uses

Used in Organic Synthesis:
Benzene, 2-chloro-4-iodo-1-methoxyis used as a key intermediate in the synthesis of various organic compounds. Its unique functional group allows for further chemical reactions, making it a valuable building block for creating specialty chemicals and other complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Benzene, 2-chloro-4-iodo-1-methoxyserves as a crucial intermediate for the production of various drugs. Its presence in the molecular structure can impart specific properties to the final drug, such as improved solubility, stability, or bioavailability.
Used in Agrochemical Industry:
Benzene, 2-chloro-4-iodo-1-methoxyis also utilized in the agrochemical industry for the synthesis of pesticides and other crop protection agents. Its unique structure can contribute to the development of more effective and targeted agrochemicals.
Used in Fine Chemicals and Dyes Production:
Benzene, 2-chloro-4-iodo-1-methoxyis used as an intermediate in the production of various fine chemicals and dyes. Its versatile functional group allows for the creation of a wide range of colorants and specialty chemicals used in different industries.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, Benzene, 2-chloro-4-iodo-1-methoxyis employed as a building block for designing new drug candidates. Its unique structure can be incorporated into potential therapeutic agents, contributing to the development of novel treatments for various diseases.

Upstream product

• 116130-33-7 2-chloro-4-iodophenol 
• 77-78-1 dimethyl sulfate 
• 75676-71-0 (3-Chloro-4-methoxy-phenyl)-pyrrolidin-1-yl-diazene 
• 766-51-8 2-Chloroanisole 
• 95-57-8 2-monochlorophenol 
• 5345-54-0 3-chloro-4-methoxyaniline 
• 696-62-8 para-iodoanisole 
• 175883-60-0 3-chloro-4-methoxyphenylboronic acid 

Downstream Products

• 31599-54-9 2-chloro-4-dichloroiodanyl-anisole 
• 414861-73-7 methyl 6-(3-chloro-4-methoxyphenyl)hex-5-ynoate 
• 118575-83-0 1-(3-Chloro-4-methoxyphenyl)indole 
• 1416164-40-3 2-methoxy-N-(4-methoxyphenyl)-5-(1-(2,4,6-trimethoxyphenyl)vinyl)aniline 
• 1379597-70-2 4,4'-((2-fluoro-1,4-phenylene)bis(ethyne-2,1-diyl))bis(2-chloro-1-methoxybenzene) 

Relevant academic research and scientific papers

Photocatalytic Oxidative Iodination of Electron-Rich Arenes

A visible-light-mediated oxidative iodination of electron-rich arenes has been developed. 2.5 mol% of unsubstituted anthraquinone as photocatalyst were used in combination with elementary iodine, trifluoroacetic acid and oxygen as the terminal oxidant. The iodination proceeds upon irradiation in non- or weakly-electron donating solvents (DCM, DCE and benzene) wherein a spectral window in strongly coloured iodine solutions can be observed at around 400 nm. The method provides good to excellent yields (up to 98%) and shows excellent regioselectivity and good functional group tolerance (triple bonds, ketone, ester, amide). Moreover, the photo-iodination was also upscaled to a 5 mmol scale (1.1 g). Mechanistic investigations by intermediate trapping and competition experiments indicate a photocatalytic arene oxidation and the subsequent reaction with iodine as a likely mechanistic pathway. (Figure presented.).

Focused ortho-Lithiation and Functionalization of p-Bromo- and p-Iodoanisole

By use of the strategy for ortho-lithiation (DoM) that conceptually diminishes the pKA difference between the ortho-H of the substrate and the conjugate acid of the metalating agent, effective metalation of bromine and iodine bearing aryl substrates can be carried out. As a set of prototypes, p-bromoanisole (p-BrA) and p-iodoanisole (p-IA) have been successfully ortho-metalated in promoted hydrocarbon media using ortho-lithiodimethylbenzylamine (o-LiDMBA) as the metalating agent. No hint of exchange of either halogen was noted using these conditions. These studies add to the emerging evidence of a hitherto unidentified acidifying effect on the proton(s) ortho- to a directing metalation group (DMG) by both a p-iodo and a p-bromo substituent.

Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes

Radiopharmaceuticals that incorporate radioactive iodine in combination with single-photon emission computed tomography imaging play a key role in nuclear medicine, with applications in drug development and disease diagnosis. Despite this importance, there are relatively few general methods for the incorporation of radioiodine into small molecules. This work reports a rapid air- and moisture-stable ipso-iododeboronation procedure that uses NIS in the non-toxic, green solvent dimethyl carbonate. The fast reaction and mild conditions of the gold-catalysed method led to the development of a highly efficient process for the radiolabelling of arenes, which constitutes the first example of an application of homogenous gold catalysis to selective radiosynthesis. This was exemplified by the efficient synthesis of radiolabelled meta-[125I]iodobenzylguanidine, a radiopharmaceutical that is used for the imaging and therapy of human norepinephrine transporter-expressing tumours.

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.

A method of preparing alkoxyl monoiodo-benzene

The invention relates to a method for preparing alkoxy iodobenzene. The method comprises the following steps: adding alkoxy benzene, I2, the catalyst nitrosonium tetrafluoroborate and an organic solvent into a reaction vessel, sealing the reaction vessel, performing a magnetic stirring reaction at the temperature of 20-60 DEG C under an airy condition, cooling to the room temperature after reaction, and performing purification on the mixture after reaction through column chromatography, so as to obtain the alkoxy iodobenzene. According to the method for preparing the alkoxy iodobenzene, any other auxiliary reagent is not added expect the catalyst and the solvent, used auxiliary material is less, the utilization rate of the iodine material under the optimum condition is high, the product purity is good, the reaction can be effectively performed at the room temperature, the production cost is remarkably reduced, and as acid is not added in the reaction system, the cost of production equipment can be lowered.

2,4,6-Tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine as a new recyclable hypervalent iodine(III) reagent for chlorination and oxidation reactions

The synthesis of 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine, as a new recyclable nonpolymeric analogue of (dichloroiodo)benzene, is achieved in two steps using 2,4,6-trichloro-1,3,5-triazine and 4-iodophenol. The application of 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine for the chlorination reaction of various activated arenes, olefin, and 1,3-diketone is demonstrated. The reagent 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine can be applied also for the oxidative synthesis of 1,3,4-oxadiazoles and 1,2,4-thiadiazoles under mild conditions in excellent yields. The recyclability of the 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine was possible owing to the facile recovery and reuse of the coproduced 2,4,6-tris(4-iodophenoxy)-1,3,5- triazine from the reaction mixture due to its practical insolubility in methanol. Georg Thieme Verlag Stuttgart, New York.

New method of synthesis and biological evaluation of some combretastatin A-4 analogues

A series of novel combretastatin A-4 analogues was synthesized in 36-64% yields by Negishi cross-coupling reaction under mild conditions. The prepared compounds exhibit good cytotoxicity against HBL100 epithelial cell lines (IC50=0.022-10.31 ). Georg Thieme Verlag Stuttgart · New York.

Facile preparation and reactivity of polystyrene-supported (dichloroiodo)benzene: A convenient recyclable reagent for chlorination and oxidation

A facile one-pot preparation of polystyrene-supported (dichloroiodo)benzene (loading of -ICl2 up to 1.35 mmol/g) from polystyrene, iodine, and bleach has been developed. This recyclable reagent is useful for efficient chlorination of organic substrates and selective oxidation of various alcohols to the corresponding carbonyl compounds in high yields under mild conditions. The final products are conveniently separated from the polymeric byproduct by simple filtration and isolated in good purity after evaporation of solvent.

Conversion of aryl iodides into aryliodine(III) dichlorides by an oxidative halogenation strategy using 30% aqueous hydrogen peroxide in fluorinated alcohol

Oxidative chlorination with HCl/H2O2 in 1,1,1-trifluoroethanol was used to transform aryl iodides into aryliodine(III) dihalides. In this instance 1,1,1-trifluoroethanol is not only the reaction medium, but is also an activator of hy

A safe and reliable procedure for the iododeamination of aromatic and heteroaromatic amines in a continuous flow reactor

A method for the safe and reliable iododeamination of aromatic and heteroaromatic amines under copper-free conditions is described and its scope is evaluated.