33348-34-4

Usage

Uses

Used in Organic Synthesis:
4-AMINO-2-IODOBENZONITRILE 98 is used as a reactant in various organic synthesis processes, including hydroamination-double hydroarylation for the synthesis of fused carbazoles, cycloisomerizations of aromatic homoand bis-homopropargylic amine/amide intermediates, asymmetric organocatalytic condensation and cycloaddition, regioselective aryl C-H bond functionalization, and synthesis of [(triisopropylsilyl)ethynyl]indole derivatives.
Used in Domino Condensation/S-arylation/Heterocyclization Reactions:
4-AMINO-2-IODOBENZONITRILE 98 is also used in domino condensation/S-arylation/heterocyclization reactions, which are important for the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Palladium-Catalyzed Carbonylation:
In the pharmaceutical industry, 4-AMINO-2-IODOBENZONITRILE 98 is used as a reactant in palladium-catalyzed carbonylation of iodoanilines, providing ketoamides in the presence of primary and secondary amines. This reaction is crucial for the synthesis of various pharmaceutical compounds and intermediates.
Overall, 4-AMINO-2-IODOBENZONITRILE 98 is a versatile and valuable compound in the field of organic chemistry, with applications in various industries, including pharmaceuticals, materials science, and chemical research. Its unique properties and reactivity make it an essential building block for the synthesis of complex organic molecules and the development of new chemical processes.

InChI:InChI=1/C7H5IN2/c8-6-3-5(4-9)1-2-7(6)10/h1-3H,10H2

Upstream product

• 516-12-1 N-iodo-succinimide 
• 873-74-5 4-Aminobenzonitrile 

Downstream Products

• 159719-57-0 4-fluoro-3-iodobenzonitrile 
• 100723-77-1 2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile 
• 183989-82-4 N-(4-cyano-2-iodophenyl)-2,2,2-trifluoroacetamide 
• 636567-56-1 (4-cyano-2-iodo-phenyl)-carbamic acid ethyl ester 
• 412947-51-4 4-amino-3-ethynylbenzonitrile 
• 450381-20-1 4-amino-3-(2-trimethylsilylethynyl)benzenecarbonitrile 
• 55586-26-0 3-hydroxy-4-aminobenzonitrile 
• 169463-44-9 5-cyano-1H-indole-2-carboxylic acid 
• 833486-33-2 3-(2-amino-5-cyanophenyl)-2-propyn-1-ol 
• 106941-22-4 4-amino-3-iodobenzylamine 

Relevant academic research and scientific papers

Thermally and Magnetically Robust Triplet Ground State Diradical

High spin (S = 1) organic diradicals may offer enhanced properties with respect to several emerging technologies, but typically exhibit low singlet triplet energy gaps and possess limited thermal stability. We report triplet ground state diradical 2 with a large singlet-triplet energy gap, ?"EST ≥ 1.7 kcal mol-1, leading to nearly exclusive population of triplet ground state at room temperature, and good thermal stability with onset of decomposition at a160 °C under inert atmosphere. Magnetic properties of 2 and the previously prepared diradical 1 are characterized by SQUID magnetometry of polycrystalline powders, in polystyrene glass, and in other matrices. Polycrystalline diradical 2 forms a novel one-dimensional (1D) spin-1 (S = 1) chain of organic radicals with intrachain antiferromagnetic coupling of J′/k = a14 K, which is associated with the N···N and N···O intermolecular contacts. The intrachain antiferromagnetic coupling in 2 is by far strongest among all studied 1D S = 1 chains of organic radicals, which also makes 1D S = 1 chains of 2 most isotropic, and therefore an excellent system for studies of low-dimensional magnetism. In polystyrene glass and in frozen benzene or dibutyl phthalate solution, both 1 and 2 are monomeric. Diradical 2 is thermally robust and is evaporated under ultrahigh vacuum to form thin films of intact diradicals on silicon substrate, as demonstrated by X-ray photoelectron spectroscopy. Based on C-K NEXAFS spectra and AFM images of the a1.5 nm thick films, the diradical molecules form islands on the substrate with molecules stacked approximately along the crystallographic a-axis. The films are stable under ultrahigh vacuum for at least 60 h but show signs of decomposition when exposed to ambient conditions for 7 h.

A Diastereoselective Route to Benzoannelated Bridged Sultams

A practical diastereoselective method for the synthesis of benzoannelated tri- and tetracyclic bridged sultams has been developed. The synthetic route employs widely available, substituted -iodoanilines and is based on intramolecular Michael addition followed by cycloalkylation with dihaloalkanes, or vice versa. The target compounds were isolated in good yields and the diastereoselectivity of the reaction could be easily controlled by the order of Michael addition and cycloalkylation steps.

New Indolo[3,2-b]indole based small organic molecules for Organic Thin Film Transistors (OTFTs): A combined experimental and DFT Study

Synthesis of new indolo[3,2-b]indoles (5a- 5j) in presence of Ag-doped ZnO and (Diacetoxyiodo) benzene system under visible-light have been reported. All the new fused linear heterocyclic indolo[3,2-b]indole systems (5a- 5j) thoroughly characterized by spectroscopic methods like mass, UV-visible, NMR and C, H, N elemental analysis. Further, their photophysical properties were carried out by combined experimental and theoretical studies. Thermogravimetric studies are carried out to confirm the thermal stability of molecules. The frontier molecular orbitals of molecules are characterized with the help of cyclic voltammetry. Additionally, the compounds of series 5 were used for the fabrication of organic thin-film transistors, which indicated the hole mobilities in the range of 0.11 – 0.85 cm2/Vs and with on/off ratio 105 on ODTS-SiO2 substrate at 50 °C and are also supported by DFT studies.

Modular counter-Fischer?indole synthesis through radical-enolate coupling

A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.

5, 10-dihydroindolo [3, 2-b] indole derivative and synthesis method and application thereof

The invention discloses a synthesis method of a 5, 10-dihydroindolo [3, 2-b] indole derivative, the method comprises the following steps: mixing a 2-((2-halogen phenyl) ethynyl)-N, N-dimethylaniline derivative (II), N, N-di-tert-butyl diazacycloketone (III), a palladium catalyst, a monophosphine ligand, alkali and a first organic solvent, and carrying out a diamidation reaction under the protection of inert gas to realize the synthesis of the 5, 10-dihydroindolo [3, 2-b] indole derivative(I). The method is easy to operate, mild in reaction condition and high in reaction yield, and the synthesized 5, 10-dihydroindolo [3, 2-b] indole derivative can be used for preparing an organic light-emitting device.

Cu(II)-Promoted Cascade Synthesis of Fused Imidazo-Pyridine-Carbonitriles

A Cu(II)-promoted synthesis of an aza-fused N-heterocycle having a benz-imidazopyridine scaffold is developed via an addition-cyclization reaction followed by an Ullmann-type C-N coupling between o-iodoanilines and γ-ketodinitriles. This protocol features a broad substrate scope, giving products in 32-84% yields. The compounds show excellent photoluminescence properties having two absorption maxima in the region between 270-280 and 338-350 nm and emission maxima in the range of 502-533 nm. The HOMO-LUMO energy gap of 3.49-3.57 eV was determined using Gaussian 09 at the B3LYP/6-31G (d, p) basis set level. We also demonstrated a few postsynthetic modifications.

A novel DMSO-assisted regioselective iodination of aniline analogues

A metal- and oxidant-free electrophilic iodination of aniline analogues was achieved in high to excellent yields at room temperature in MTBE with 0 or 3.5 equivalents of DMSO. Examined substituents include N-alkyl, N,N-dialkyl, N-morpholinyl and N-piperazinyl as well as methyl, Br, CN and CO2CH3 aryl ring substitutions.

Intramolecular Hydroamination of Selenoalkynes to 2-Selenylindoles in the Absence of Catalyst

In this work, a series of 2-chalcogenylindoles was synthesized by an efficient methodology, starting from chalcogenoalkynes, including a previously unreported tellurium indole derivative. For the first time, these 2-substituted chalcogenylindoles were obtained in the absence of metal catalyst or base, under thermal conditions only. In addition, the results described herein represent a methodology with inverse regioselectivity for the chalcogen functionalization of indoles.

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.).

Molecular Scaffolds as Double-Targeting Agents For the Diagnosis and Treatment of Neuroblastoma

The selective delivery of therapeutic and imaging agents to tumoral cells has been postulated as one of the most important challenges in the nanomedicine field. Meta-iodobenzilguanidine (MIBG) is widely used for the diagnosis of neuroblastoma (NB) due to its strong affinity for the norepinephrine transporter (NET), usually overexpressed on the membrane of malignant cells. Herein, a family of novel Y-shaped scaffolds has been synthesized, which have structural analogues of MIBG covalently attached at each end of the Y-structure. The cellular uptake capacity of these double-targeting ligands has been evaluated in vitro and in vivo, yielding one specific Y-shaped structure that is able to be engulfed by the malignant cells, and accumulates in the tumoral tissue, at significantly higher levels than the structure containing only one single targeting agent. This Y-shaped ligand can provide a powerful tool for the current treatment and diagnosis of this disease.