3824-22-4

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluoro-2-iodo-1-methoxybenzene is used as a building block for the synthesis of various biologically active compounds. Its unique chemical structure allows it to be a valuable intermediate in the development of new drugs, contributing to the creation of pharmaceuticals with novel therapeutic properties and potential applications in treating a range of diseases.
Used in Agrochemical Industry:
In the agrochemical industry, 4-Fluoro-2-iodo-1-methoxybenzene serves as a key component in the synthesis of bioactive molecules. It is utilized to develop new agrochemicals with enhanced efficacy and selectivity, which can improve crop protection and contribute to sustainable agriculture.
Used in Organic Synthesis:
4-Fluoro-2-iodo-1-methoxybenzene is employed as a versatile reagent in organic synthesis. Its ability to participate in carbon-carbon and carbon-heteroatom bond formation makes it a valuable tool for chemists in constructing complex organic molecules and developing new synthetic routes.
Used in the Development of New Materials:
The unique chemical structure of 4-Fluoro-2-iodo-1-methoxybenzene also makes it a promising intermediate for the development of new materials. Its properties can be harnessed to create innovative materials with specific characteristics, such as improved stability, reactivity, or selectivity, which can be applied in various industries, including electronics, coatings, and adhesives.

InChI:InChI=1/C7H6FIO/c1-10-7-3-2-5(8)4-6(7)9/h2-4H,1H3

Upstream product

• 1978-39-8 5-fluoro-2-methoxy-aniline 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 2713-29-3 2-iodo-4-fluorophenol 
• 74-88-4 methyl iodide 
• 371-41-5 4-Fluorophenol 
• 394-04-7 5-fluoro-2-methoxybenzoic acid 
• 445-83-0 4-fluoro-1-methoxy-2-nitrobenzene 

Downstream Products

• 2713-29-3 2-iodo-4-fluorophenol 
• 5400-65-7 2,2'-dimethoxy-4,4'-difluorobiphenyl 
• 81890-66-6 4-fluoro-2-(2-methylphenoxy)anisole 
• 741712-82-3 (4-amino-2-ethylsulfanylpyrimidin-5-yl)(5-fluoro-2-methoxyphenyl)methanone 
• 1238892-12-0 4-fluoro-1-methoxy-2-(phenylethynyl)benzene 
• 36665-50-6 5-fluoro-2-methoxy-1,3-dimethylbenzene 
• 791068-92-3 5-fluoro-2-methoxy-1,1'-biphenyl 
• 451-91-2 (4-fluoro-2-iodo-phenoxy)-acetic acid 

Relevant academic research and scientific papers

Pd-Catalyzed ipso, meta-Dimethylation of ortho-Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source

A methyl group can have a profound impact on the pharmacological properties of organic molecules. Hence, developing methylation methods and methylating reagents is essential in medicinal chemistry. We report a palladium-catalyzed dimethylation reaction of ortho-substituted iodoarenes using dimethyl carbonate as a methyl source. In the presence of K2CO3 as a base, iodoarenes are dimethylated at the ipso- and meta-positions of the iodo group, which represents a novel strategy for meta-C-H methylation. With KOAc as the base, subsequent oxidative C(sp3)-H/C(sp3)-H coupling occurs; in this case, the overall transformation achieves triple C-H activation to form three new C-C bonds. These reactions allow expedient access to 2,6-dimethylated phenols, 2,3-dihydrobenzofurans, and indanes, which are ubiquitous structural motifs and essential synthetic intermediates of biologically and pharmacologically active compounds.

Entry to 1,2,3,4-Tetrasubstituted Arenes through Addressing the " Meta Constraint" in the Palladium/Norbornene Catalysis

Arenes with four different contiguous substituents, i.e. 1,2,3,4-tetrasubstituted arenes, are commonly found in bioactive compounds, but they are nontrivial to access via conventional methods. Through addressing the "meta constraint" in the palladium/norbornene (Pd/NBE) cooperative catalysis, which is the difficulty of tolerating a sizable meta substituent in aryl halide substrates, here a modular and regioselective approach is realized for preparing 1,2,3,4-tetrasubstituted arenes. One key is the use of a C2-amide-substituted NBE, and a combined experimental and computational study reveals its role in promoting the NBE insertion and the ortho C-H metalation steps. The scope is broad: A variety of electrophiles and nucleophiles could be introduced to the ortho and ipso positions, respectively, with 1,4-disubstituted aryl halides, leading to diverse unsymmetrical contiguous tetrasubstituted arenes. Application of this approach has been demonstrated in streamlined syntheses of several bioactive compounds.

Decarboxylative Suzuki-Miyaura coupling of (hetero)aromatic carboxylic acids using iodine as the terminal oxidant

A novel methodology for the decarboxylative Suzuki-Miyaura-type coupling has been established. This process uses iodine or a bromine source as both the decarboxylation mediator and the terminal oxidant, thus avoiding the need for stoichiometric amounts of transition metal salts previously required. Our new protocol allows for the construction of valuable biaryl architectures through the coupling of (hetero)aromatic carboxylic acids with arylboronic acids. The scope of this decarboxylative Suzuki reaction has been greatly diversified, allowing for previously inaccessible non-ortho-substituted aromatic acids to undergo this transformation. The procedure also benefits from low catalyst loadings and the absence of stoichiometric transition metal additives.

Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings

Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.

Gold(I)-catalyzed iodination of arenes

A wide variety of electron-rich arenes were efficiently converted into the corresponding iodinated compounds via a gold(I)-catalyzed reaction under mild conditions. Georg Thieme Verlag Stuttgart. New York.

Iodine(I) reagents in hydrochloric acid-catalyzed oxidative iodination of aromatic compounds by hydrogen peroxide and iodine

Hydrochloric acid activates the oxidative iodination of aromatic compounds with the iodine- hydrogen peroxide system through the formation of an iodine(I) compound as the iodinating reagent. Activation with hydrochloric acid is more powerful than that with sulfuric acid. The formation of dichloroiodic(I) acid (HICl2) with various forms of hydrogen peroxide was followed using UV spectroscopy. The HICl2 was used as the iodinating reagent. In the preparative oxidative iodinaton of various aromatic compounds, hydrochloric acid was used in a catalytic amount and the iodine(I) reagent was formed in situ with 0.5 equiv. hydrogen peroxide and 0.5 equiv. molecular iodine. Two types of reactivity were observed in oxidative iodination with iodine(I) species catalyzed by hydrochloric acid: in the iodination of anisole 1a better yields of iodination were observed with a smaller amount of hydrochloric acid, while on the contrary 4-tert-butyltoluene 1b gave better yields of iodination upon increasing the amount of hydrochloric acid. Reactivity was further manipulated by the choice of the solvent (MeCN, trifluoroethanol, hexafluoro-2-propanol). Copyright

Room temperature regioselective iodination of aromatic ethers mediated by Selectfluor(TM) reagent F-TEDA-BF4

Monosubstituted phenyl ethers were regioselectively iodinated with a mixture of iodine and F-TEDA in acetonitrile at room temperature at the para position, while 1-methoxy-4-substituted benzene derivatives were converted to 2-iodo products in high yield.