40400-15-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Iodophenylacetonitrile is used as a synthetic intermediate for the preparation of various pharmaceutical compounds. Its ability to react with lactams to form ring-fused isoquinolinones makes it a valuable component in the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
2-Iodophenylacetonitrile is used as a key building block in the synthesis of various organic compounds, including:
1. 2?-aminobiphen-2-ylacetonitrile
2. Ethyl (2-iodophenyl)iminoacetate hydrochloride
3. 3,4-disubstituted 2-naphthalenamines
These compounds have potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.
Used in the Preparation of Nitriles:
2-Iodophenylacetonitrile is also utilized in the preparation of several nitriles, which are important intermediates in the synthesis of various organic compounds. Some of these nitriles include:
1. 2-(2-iodophenyl)-2-methylpropanenitrile
2. 1-(2-iodophenyl)cyclopentanecarbonitrile
3. 5-bromo-2-(2-iodophenyl)pentanenitrile
4. 2-(2-iodophenyl)-2-propylpentanenitrile
5. 1-(2-iodophenyl)cyclohexanecarbonitrile
6. 1-(2-Iodophenyl)cyclopropanecarbonitrile
These nitriles can be further modified and used in the development of new compounds with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C8H6IN/c9-8-4-2-1-3-7(8)5-6-10/h1-4H,5H2

Upstream product

• 40400-13-3 2-Iodobenzyl bromide 
• 143-33-9 sodium cyanide 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 17729-59-8 tri-n-butyl(cyanomethyl)stannane 
• 140-29-4 phenylacetonitrile 
• 773837-37-9 sodium cyanide 
• 615-37-2 ortho-methylphenyl iodide 
• 5159-41-1 2-iodobenzyl alcohol 
• 183789-20-0 2-iodobenzyl methanesulfonate 
• 591-50-4 iodobenzene 
• 75-05-8 acetonitrile 
• 164594-13-2 Phenyl[2-(trimethylsilyl)phenyl]iodonium trifluoromethanesulfonate 
• 4622-38-2 2-iodobenzyliodide 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 76574-72-6 6-(2-Iodo-phenyl)-2-methyl-pyrido[2,3-d]pyrimidin-7-ylamine 
• 87033-46-3 2-(2-hydroxymethylphenylthio)phenylacetonitrile 
• 76574-56-6 6-(2-Iodo-phenyl)-pyrido[2,3-d]pyrimidin-7-ylamine 
• 219679-04-6 5-bromo-2-(2-iodophenyl)pentanenitrile 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 17459-91-5 cis-erythrinane 
• 809233-37-2 1-[2-(2-iodophenyl)ethyl]octahydroindole-7a-carbonitrile 
• 809233-33-8 [2-(1,4-dioxaspiro[4.5]dec-6-yl)ethyl]-[2-(2-iodophenyl)ethyl]amine 
• 1012327-03-5 2-(2-iodophenyl)-3,3-bis(methylthio)acrylonitrile 

Relevant academic research and scientific papers

Long-Lived, Strongly Emissive, and Highly Reducing Excited States in Mo(0) Complexes with Chelating Isocyanides

Newly discovered tris(diisocyanide)molybdenum(0) complexes are Earth-abundant isoelectronic analogues of the well-known class of [Ru(α-diimine)3]2+ compounds with long-lived 3MLCT (metal-to-ligand charge transfer) excited

Selective ortho C?H Cyanoalkylation of (Diacetoxyiodo)arenes through [3,3]-Sigmatropic Rearrangement

We herein report a robust catalyst-free cross-coupling between ArI(OAc)2 and α-stannyl nitriles, aided by TMSOTf. The transformation introduces a cyanoalkyl group to the ortho position of ArI(OAc)2 and simultaneously reduces the aryl iodine(III) to iodide, thus providing α-(2-iodoaryl) nitrile as the product. This transformation could be completed within 5 min at ?78 °C and features superb functional-group tolerance and efficient scalability. DFT calculations indicate that the formation of a ketenimine(aryl)iodonium intermediate and subsequent [3,3]-sigmatropic rearrangement are involved as key steps.

Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.

Approach to the synthesis of indoline derivatives from diaryliodonium salts

An effective method of constructing the indoline moiety via intramolecular nucleophilic ring closure of a diaryliodonium salt is described. Diacetoxyiodoarene compounds (1a-1e) were converted into intermediate Koser's reagent and coupled with arylstannanes (7-10) to form diaryliodonium salts (11a-14e). Indoline compounds with different N-protecting groups, 15, 16, 17, and 18, were synthesized in higher yields by treating salts (11a-14e) with Cs2CO3 and TEMPO. Regardless of the electronic environment of five para-substituted iodoarenes and the natures of four N-protected arylstannane groups, the conversion proceeded well to afford corresponding indolines in yields of 72-84 and 70-84%, respectively.

Mo(CO)6-mediated carbamoylation of aryl halides

A simple method for the synthesis of amides has been developed by molybdenum-mediated carbamoylation of aryl halides. Whereas the conventional palladium-catalyzed three-component coupling reaction requires a large excess of gaseous carbon monoxide, the incorporation of carbon monoxide in this Mo-mediated carbamoylation reaction is so efficient that it requires only a slight excess amount of carbon monoxide in the form of its molybdenum complex, Mo(CO)6. The reaction is applicable for the synthesis of a wide variety of not only secondary and tertiary amides but also primary amides by using aqueous ammonia.

A mild inter- and intramolecular amination of aryl halides with a combination of CuI and CsOAc

A unique combination of CuI and CsOAc was found to catalyze aryl amination under mild conditions. The reaction takes place at room temperature or at 90 °C with broad functional group compatibility. The intramolecular reaction was able to form five-, six-, and seven-membered rings with various protecting groups on the nitrogen atom. The scope of the intermolecular amination, as well as its applications to unsymmetrical N,N′-dialkylated phenylenediamines, was investigated.

Facile one-pot synthesis of 2-aryl-substituted nitriles and 2-aryl-3-keto nitriles via benzyne reaction

2-Aryl-substituted nitriles were prepared in good to excellent yields in a one-pot reaction by the reaction of benzyne, generated using neutral conditions from (phenyl)[o-(trimethylsilyl)-phenyl]iodonium triflate, and 2-lithionitriles. 3-Keto nitriles substituted at the 2-position were obtained in good yields when these reactions were trapped with acid chlorides. The mechanism of the benzyne reaction in terms of a N-lithiobenzocyclobutanimine intermediate is discussed. Copyright Taylor & Francis Group, LLC.

A new synthesis of phenolic 1-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-Benzazepines

7,8-Dihydroxy-1-phenyl- and 1-(3- and 4-hydroxyphenyl)-1-hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepine derivatives (2a,b) and (3a-c) were synthesized by intramolecular Barbier reaction of N-(2-iodophenethyl)-phenacylamines (5a,b) and (12a-c) with n-C4

Copper(I) mediated intramolecular cyclization of 2-(2-amino-phenylethynyl)benzoic and [2-(2-aminophenylethynyl)phenyl]acetic acid esters: A new synthetic step towards isoindolo[2,1-a]indoles and 5H-indolo[2,1-a]isoquinolines

We describe herein parallel synthetic routes to isoindolo[2,1-a]indoles and 5H-indolo[2,1-a]isoquinolines from 2-(2-aminophenylethynyl)benzoic acid esters and [2-(2-aminophenylethynyl)phenyl]acetic acid esters, respectively.