19230-45-6

Usage

Uses

Used in Pharmaceutical Synthesis:
N-(3-iodophenyl)acetamide is used as a key intermediate in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
As an intermediate in organic synthesis, N-(3-iodophenyl)acetamide plays a crucial role in the preparation of a wide range of chemical compounds, facilitating the advancement of chemical research and innovation.
Used in Chemical Compound Preparation:
N-(3-iodophenyl)acetamide is employed in the preparation of other chemical compounds, expanding its applications across different industries and contributing to the diversification of chemical products.
Used in Biological Activity Research:
N-(3-iodophenyl)acetamide has been studied for its potential biological activities, indicating its possible use in the development of new biological agents or for understanding specific biological processes.
It is important to handle N-(3-iodophenyl)acetamide with proper precautions due to its potential harmful effects if ingested, inhaled, or in contact with skin and eyes.

Upstream product

• 108-24-7 acetic anhydride 
• 626-01-7 3-Iodoaniline 
• 78887-39-5 3-Acetamidophenylboronic acid 
• 75-05-8 acetonitrile 
• 762-72-1 allyl-trimethyl-silane 
• 645-00-1 m-iodonitrobenzene 
• 75-36-5 acetyl chloride 
• 457658-05-8 N-meta-iodophenyl urea 

Downstream Products

• 110179-19-6 (3-acetylamino-phenyl)-phenyl-iodonium ; iodide 
• 93298-15-8 N-[3-((E)-3-Oxo-pent-1-enyl)-phenyl]-acetamide 
• 93298-26-1 N-{3-[1-(3-Acetylamino-phenyl)-3-oxo-pentyl]-phenyl}-acetamide 
• 104581-39-7 N-{3-[1-(3-Acetylamino-phenyl)-3-hydroxy-3-methyl-but-1-enyl]-phenyl}-acetamide 
• 93298-23-8 N-{3-[1-(3-Acetylamino-phenyl)-3-oxo-butyl]-phenyl}-acetamide 
• 93080-25-2 N-[3-((Z)-1,2-Diphenyl-vinyl)-phenyl]-acetamide 
• 104581-30-8 2-methyl-4-(3-acetylaminophenyl)-3-butyn-2-ol 
• 38382-44-4 5-Iod-1,2,3,4-tetraphenylnaphthalin 
• 164470-57-9 3-(3'-oxoprop-1'-yl)acetanilide 
• 130721-59-4 4-methylene-3-(toluene-4-sulfonyl)-1-oxa-3-azaspiro[4.5]decan-2-one 
• 860218-60-6 acetic acid-(3-iodosyl-anilide) 
• 117864-12-7 3-Amino-diphenyliodonium-iodid 
• 1428370-17-5 4-acetamido-2-iodophenyl trifluoromethanesulfonate 

Relevant academic research and scientific papers

Direct para-Selective C-H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines

Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most importantly, this reaction can be easily scaled up to the ten-gram scale, highlighting its synthetic utility. The mechanistic study revealed that the in situ generated aryl hypervalent iodine intermediate is the key factor to realize this para-selective C-H amination reaction.

Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation

The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.

NEAR-INFRARED NERVE-SPARING BENZO[C]PHENOXAZINE FLUOROPHORES

Provided are near-infrared nerve-sparing fluorescent compounds, compositions comprising them, and methods of their use in medical procedures.

Synthesis of Arylamides via Ritter-Type Cleavage of Solid-Supported Aryltriazenes

A novel route for the synthesis of N-arylamides via the cleavage of aryltriazenes with alkyl or aryl nitriles is presented. We developed a variation of the Ritter reaction that allows the use of acetonitrile as solvent and reagent in reactions with solid-supported precursors. The reaction was optimized for the generation of N-aryl acetamides using a diverse range of immobilized building blocks including o-, m-, and p-substituted aryltriazenes. The cleavage via the Ritter-type conversion was combined with an on-bead cross-coupling reaction of halogen-substituted aryltriazenes with pyrazoles. Additionally, the synthesis of on-bead generated arylboronic ester-substituted triazenes was shown. The developed procedure was further expanded to use other commercially available nitriles, such as acrylonitrile, benzonitrile, and chlorinated alkyl nitriles as suitable reagents for a Ritter-type cleavage of the prepared triazene linkers.

Thermolysis and radiofluorination of diaryliodonium salts derived from anilines

Aniline-derived diaryliodonium salts were synthesized and functionalized in good to excellent yields by judicious utilization of electron-withdrawing protecting groups. This simple approach opens another route to radiolabeling amino arenes in relatively complex molecules, such as flutemetamol.

Mild and efficient palladium-catalyzed direct trifluoroethylation of aromatic systems by C-H activation

The introduction of trifluoroalkyl groups into aromatic molecules is an important transformation in the field of organic and medicinal chemistry. However, the direct installation of fluoroalkyl groups onto aromatic molecules still represents a challenging and highly demanding synthetic task. Herein, a simple trifluoroethylation process that relies on the palladium-catalyzed C-H activation of aromatic compounds is described. With the utilization of a highly active trifluoroethyl(mesityl)iodonium salt, the developed catalytic method enables the first highly efficient and selective trifluoroethylation of aromatic compounds. The robust catalytic procedure provides the desired products in up to 95 % yield at 25 °C in 1.5 to 3 hours and tolerates a broad range of functional groups. The utilization of hypervalent reagents opens new synthetic possibilities for direct alkylations and fluoroalkylations in the field of transition-metal-catalyzed C-H activation.

IODINE(III)-MEDIATED RADIOFLUORINATION

A process for fluorination of aromatic compounds employing iodonium ylides and applicable to radiofluorination using 18F is described. Processes, intermediates, reagents and radiolabelled compounds are described.

A practical and general ipso iodination of arylboronic acids using N-iodomorpholinium iodide (NIMI) as a novel iodinating agent: mild and regioselective synthesis of aryliodides

A mild and efficient protocol for the ipso-iodination of aryl boronic acids using N-iodomorpholinium iodide (NIMI) generated in situ from morpholine and molecular iodine as a novel iodinating agent has been developed. The addition of a catalytic amount of copper iodide found to promote rate enhancement of the iodination reaction and dramatic increase in the yield depending upon the nature of the boronic acid was observed. The mechanistic study revealed that depending upon the nature of the substrate, either the classical ipso substitution or copper catalysed iododeborylation pathway overall dominates the present iodination reaction. The features such as mild reaction conditions, operational simplicity, high to excellent yields, excellent functional group compatibility and low catalyst loading make this method potentially useful in organic synthesis.

Ti/Ni-mediated inter- and intramolecular conjugate addition of aryl and alkenyl halides and triflates

In this work, we show that the unique combination of a nickel catalyst and Cp2TiCl allows the direct conjugate addition of aryl and alkenyl iodides, bromides, and to a lesser extent, chlorides and triflates to α,β-unsaturated carbonyls at room temperature, without requiring the previous formation of an organometallic nucleophile. The reaction proceeds inter- and intramolecularly with good functional group compatibility, which is key for the development of free protecting group methodologies. Carbo- and heterocycles of five- and six-membered rings are obtained in good yields. Moreover, some insights about the mechanism involved have been obtained from cyclic voltammetry, UV-vis, and HRTEM measurements.

Oxidative para- Triflation of acetanilides

Direct triflation of acetanilide derivatives with silver triflate has been accomplished under mild iodine(III)-mediated oxidative conditions. The reaction shows excellent regioselectivity for the para position and tolerates a range of ortho and meta substituents on the aromatic ring. This method is also compatible with the preparation of arylnonaflates in synthetically useful yields.