cas 20691-72-9, 4-Iodo-2-nitroaniline | Articles data

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NCBSI/KI: A Reagent System for Iodination of Aromatics through in Situ Generation of I-Cl
In situ iodine monochloride (I-Cl) generation followed by iodination of aromatics using NCBSI/KI system has been developed. The NCBSI reagent requires no activation due to longer bond length, lower bond dissociation energy, and higher absolute charge density on nitrogen. The system is adequate for mono- and diiodination of a wide range of moderate to highly activated arenes with good yield and purity. Moreover, the precursor N-(benzenesulfonyl)benzenesulfonamide can be recovered and transformed to NCBSI, making the protocol eco-friendly and cost-effective.
Palav, Amey,Misal, Balu,Chaturbhuj, Ganesh
p. 12467 - 12474
(2021/08/24)

Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes
Owing to both Lewis and Bronsted acid active sites on sulfated polyborate under homogenous conditions, we were keen on developing iodination protocol of arenes that can meet the requirement of regioselectivity and higher yield. The sulfated polyborate activates N-iodosuccinimide for mono iodination of highly activated substrates viz. phenols, anilines under anhydrous condition. Water tunes sulfated polyborate to generate more Bronsted acid sites resulting in rapid activation of NIS for diiodination. The protocol was equally applicable to diiodination of 4-hydroxyphenylacetic acid to synthesize 4-hydroxy-3,5-diiodophenylacetic acid, an intermediate of tiratricol, a thyroid treatment drug. This protocol was further integrated via one-pot sequential iodination and Sonogashira coupling to synthesize aryl acetylenes, building blocks for the synthesis of a variety of specialty chemicals, API, and natural products.
Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh
supporting information

(2021/05/26)

A novel ternary approach to quantitatively assess the reactivity of nitroaniline regioisomers by investigation of rapid iodination kinetics using hydrodynamic voltammetry, reduction propensities from polarography, and binding affinities from molecular docking simulations
A novel ternary approach to assess the reactivity of nitroaniline regioisomers on a quantitative scaffold has been manifested on the basis of three complementary tenets: kinetics, polarography, and molecular docking. Data from investigation of rapid iodination kinetics of nitroaniline regioisomers by hydrodynamic voltammetry in aqueous medium, reduction propensities of these regioisomers from polarography, and their binding affinities with hypoxanthine-guanine phophoribosyltransferase (HPRT1) from molecular docking simulations lead to inferences regarding their reactivity that agree in entirety. The experimentally determined magnitudes of the specific reaction rates, energies of activation, collision frequencies, entropies of activation from kinetic studies, and reduction propensities of nitroaniline regioisomers from polarograms when complemented with in silico binding energies of these regioisomer ligands with the receptor enzyme, assess their relative reactivities in unison on a quantitative scaffold. This novel ternary approach unambiguously assesses the reactivity of the regioisomers of nitroaniline as 4-nitroaniline?>?2-nitroaniline?>?3-nitroaniline.
Borkar, Vitthal T.
p. 1193 - 1202
(2021/07/31)

Sodium sulfate-hydrogen peroxide-sodium chloride adduct: selective protocol for the oxidative bromination, iodination and temperature dependent oxidation of sulfides to sulfoxides and sulfones
The regioselective bromination and iodination of unprotected aromatic primary amines using enclathrated hydrogen peroxide as an oxidant under mild conditions has been developed, in which potassium bromide (KBr) and potassium iodide (KI) were used as brominating and iodinating agents, respectively. The adduct shows not only regioselectivity for para- or ortho-isomers but also a remarkable chemoselectivity for monobromination. Selective oxidation of sulfides to sulfoxides and sulfones has also been studied and good to excellent yields of the desired products were obtained. Acetic acid was found to be the solvent of choice for these reactions. This simple method represents an ecologically benign and alternative pathway for the oxidative halogenation of anilines and the oxidation of sulfides to sulfoxides and sulfones.
Gayakwad, Eknath M.,Patel, Khushbu P.,Shankarling, Ganapati S.
supporting information
p. 6001 - 6009
(2019/04/17)

Preparation method of 2-bromo-5-iodophenol
The invention discloses an industrial preparation method of 2-bromo-5-iodophenol. According to the industrial preparation method of the 2-bromo-5-iodophenol, ortho-nitroaniline serves as an initial raw material, and the 2-bromo-5-iodophenol is synthesized by iodination, diazotization bromination, reduction and diazotization phenol hydroxylation four-step reaction. The 2-bromo-5-iodophenol obtainedin the process is blue solid with the purity of 97.5%, raw material conversion rate in each step reaches 100%, and the total yield of the whole process reaches 17%.
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Paragraph 0005; 0013

(2019/03/08)

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol
Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.
Tang, Ren-Jin,Milcent, Thierry,Crousse, Benoit
p. 930 - 938
(2018/01/28)

Iodination of industrially important aromatic compounds with aqueous potassium triiodide
A new reagent system consisting of aqueous KI3in AcOH and NaIO4as oxidant has been found to be effective in iodinating a variety of commercially important aromatic substrates under ambient conditions. The presence of Na2SO3enhances the yield and the product purity. The procedure ensures high yields (72–98%) at room temperature in a short reaction time. A remarkable feature of this system is that even acidsensitive functionalities like anilines can be iodinated quantitatively.
Sharma,Srivastava,Agarwal,Diwedi
p. 433 - 436
(2016/06/13)

Exploring the Strength of the H-Bond in Synthetic Models for Heme Proteins: The Importance of the N?H Acidity of the Distal Base
The distal hydrogen bond (H-bond) in dioxygen-binding proteins is crucial for the discrimination of O2with respect to CO or NO. We report the preparation and characterization of a series of ZnIIporphyrins, with one of three meso-phenyl rings bearing both an alkyl-tethered proximal imidazole ligand and a heterocyclic distal H-bond donor connected by a rigid acetylene spacer. Previously, we had validated the corresponding CoIIcomplexes as synthetic model systems for dioxygen-binding heme proteins and demonstrated the structural requirements for proper distal H-bonding to CoII-bound dioxygen. Here, we systematically vary the H-bond donor ability of the distal heterocycles, as predicted based on pKavalues. The H-bond in the dioxygen adducts of the CoIIporphyrins was directly measured by Q-band Davies-ENDOR spectroscopy. It was shown that the strength of the hyperfine coupling between the dioxygen radical and the distal H-atom increases with enhanced acidity of the H-bond donor.
Alberti, Mariza N.,Polyhach, Yevhen,Tzirakis, Manolis D.,T?dtli, Laura,Jeschke, Gunnar,Diederich, Fran?ois
supporting information
p. 10194 - 10202
(2016/07/19)

Regioselective iodination of aryl amines using 1,4-dibenzyl-1,4-diazoniabicyclo [2.2.2] octane dichloroiodate in solution and under solvent-free conditions
1,4-Dibenzyl-1,4-diazoniabicyclo[2.2.2]octane dichloroiodate is an efficient and regioselective reagent for iodination of aryl amines. A wide variety of aryl amines in reaction with this reagent afforded regioselectively iodinated products. The iodination reaction can be carried out in solution or under solvent-free condition at room temperature.
Alikarami, Mohammad,Nazarzadeh, Somayeh,Soleiman-Beigi, Mohammad
p. 157 - 162
(2015/01/30)

Greener iodination of arenes using sulphated ceria-zirconia catalysts in polyethylene glycol
An environmentally benign method for the selective monoiodination of diverse aromatic compounds has been developed using reusable sulphated ceria-zirconia under mild conditions. The protocol provides moderate to good yields and selectively introduces iodine at the para/ortho position in monosubstituted arenes. SO42-/Ce0.07Zr 0.93O2 was found to be the best choice for the synthesis of aryl iodides in high yield, presumably due to the maximum number of acid sites (4.23 mmol g-1) among the various compositions of the catalyst system.
Kahandal, Sandeep S.,Kale, Sandip R.,Gawande, Manoj B.,Zboril, Radek,Varma, Rajender S.,Jayaram, Radha V.
p. 6267 - 6274
(2014/01/23)

Synthesis and biological evaluation of novel 2,3-dihydro-1H-1,5- benzodiazepin-2-ones; Potential imaging agents of the metabotropic glutamate 2 receptor
A focused library of novel 2,3-dihydro-1H-1,5-benzodiazepin-2-ones containing sites for 11C-, 18F- and 123I- labelling have been prepared and evaluated against membrane expressing human recombinant metabotropic glutamate 2 receptor (mGluR2). The compounds were found to be non-competitive antagonists with nanomolar affinity. HPLC evaluation of the physiochemical properties of these compounds identified two candidates for PET and SPECT imaging of mGluR2.
Gilfillan, Lynne,Blair, Adele,Morris, Brian J.,Pratt, Judith A.,Schweiger, Lutz,Pimlott, Sally,Sutherland, Andrew
supporting information
p. 1118 - 1123
(2013/07/26)

INHIBITORS OF HCV NS5A
Provided herein are compounds, pharmaceutical compositions and combination therapies for inhibition of hepatitis C.
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Page/Page column 115; 116

(2011/12/14)

INHIBITORS OF HCV NS5A
Provided herein are compounds, pharmaceutical compositions and combination therapies for inhibition of hepatitis C.
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Page/Page column 115-116

(2010/06/20)

A practical iodination of aromatic compounds by using iodine and iodic acid
This article describes simple and efficient method for the iodination of different aromatic amines, hydroxy aromatic aldehydes, hydroxy acetophenones and phenols using iodine and iodic acid in ethanol as a solvent. Notable advantages include mild reaction condition, no need of catalyst, short reaction time, simple practical procedure, giving excellent yield of the product. Copyright Taylor & Francis Group, LLC.
Shinde, Avinash T.,Zangade, Sainath B.,Chavan, Shivaji B.,Vibhute, Archana Y.,Nalwar, Yogesh S.,Vibhute, Yeshwant B.
experimental part
p. 3506 - 3513
(2011/02/22)

The [Cu]-catalyzed SNAR reactions: Direct amination of electron deficient aryl halides with sodium azide and the synthesis of arylthioethers under Cu(II) - Ascorbate redox system
A one pot [Cu]-promoted SNAr reaction of electron-deficient halobenzenes with sodium azide and the reduction of the intermediate aryl azides under the same Cu(II)-ascorbate redox conditions leading to anilines has been documented. Control experiments revealed that both ascorbate and proline play important role in the reaction path way. Further, the use of this catalytic Cu(II)-ascorbate redox system has been explored for the synthesis of arylthioethers.
Goriya, Yogesh,Ramana
experimental part
p. 7642 - 7650
(2010/12/19)

Convenient and efficient method for the iodination of aromatic amines by pyridinium iodochloride
A simple and efficient method for the iodination of aromatic amines using pyridinium iodochloride (PyICl) in methanol as solvent is reported. Mild reaction conditions, short reaction time, and good to excellent yields of the product are the noteworthy advantages of the method. Pyridinium iodochloride is an efficient solid iodinating reagent and can be handled safely. Copyright Taylor & Francis Group, LLC.
Khansole, Sandeep V.,Junne, Subhash B.,Sayyed, Mudassar A.,Vibhute, Yeshwant B.
p. 1792 - 1798
(2008/09/20)

Iodination of aromatic compounds using potassium iodide and hydrogen peroxide
A simple, efficient, regioselective, and ecofriendly method for oxyiodination of aromatic compounds is presented. In this method, the electrophilic substitutions of iodine generated in situ from KI as an iodine source and hydrogen peroxide as an oxygen source have been employed without any catalyst/mineral acid for the first time. Copyright Taylor & Francis Group, LLC.
Reddy, K. Suresh Kumar,Narender,Rohitha,Kulkarni
experimental part
p. 3894 - 3902
(2009/04/04)

NaIO4/KI/NaCl: a new reagent system for iodination of activated aromatics through in situ generation of iodine monochloride
A new reagent system consisting of NaIO4/KI/NaCl in aq AcOH has been found to be effective in iodinating a variety of activated aromatic substrates via in situ-generated iodine monochloride, to furnish iodoaromatics in excellent yields. This iodination procedure has been applied successfully for a cost-effective synthesis of 3,3′-diaminobenzidine, a key intermediate for preparing proton conducting membranes for fuel cell applications, with high yield and a purity of 99.7%.
Emmanuvel, Lourdusamy,Shukla, Ravi Kant,Sudalai, Arumugam,Gurunath, Suryavanshi,Sivaram, Swaminathan
p. 4793 - 4796
(2007/10/03)

Benzo[1,2-c]1,2,5-oxadiazole N-oxide derivatives as potential antitrypanosomal drugs. Part 3: Substituents-clustering methodology in the search for new active compounds
The results of a study on the use of Hansch's series design, cluster methodology, for the generation of new benzo[1,2-c]1,2,5-oxadiazole N-oxide derivatives as antitrypanosomal compounds are described. In vitro activity of these compounds was tested against Tulahuen 2 strain of Trypanosoma cruzi. Clearly, the Hansch methodology allowed identifying two cluster-substituents suitable for further structural modifications. The most effective drugs, derivatives 11, 18, and 21, with 50% inhibitory concentration (IC50) of the same order as that of the reference drug, represent an excellent structural point of chemical modifications for the design of future drugs. Preliminary results from the study of the mechanism of action of these benzofuroxans point to perturbation of the mitochondrial electron chain, inhibiting parasite respiration.
Aguirre, Gabriela,Boiani, Lucia,Cerecetto, Hugo,Di Maio, Rossanna,Gonzalez, Mercedes,Porcal, Williams,Denicola, Ana,Moeller, Matias,Thomson, Leonor,Tortora, Veronica
p. 6324 - 6335
(2007/10/03)

Synthesis of functionalized nitroarylmagnesium halides via an iodine-magnesium exchange
(Chemical Equation Presented) Various nitro-substituted aryl and heteroaryl iodides undergo an iodine-magnesium exchange reaction when treated with PhMgCl leading to nitro-containing magnesium organometallics. These Grignard reagents display an excellent stability at temperatures below -40°C and do not undergo electron-transfer reactions. They react as expected with various electrophiles.
Sapountzis, Ioannis,Dube, Henry,Lewis, Robert,Gommermann, Nina,Knochel, Paul
p. 2445 - 2454
(2007/10/03)

Polymer-supported organotin reagents for regioselective halogenation of aromatic amines
(Chemical Equation Presented) Polymer-supported triorganotin halides were used in the halogenation reaction of aromatic amines. Treatment of aromatic amines with n-butyllithium and polymer-supported organotin halides gave the corresponding polymer-bound N-triorganostannylamines, which by treatment with bromine or iodine monochloride gave the para-halogenated aromatic amines with high yields and high selectivities. The polymer-supported organotin halides reagents regenerated during the course of the halogenation reaction can be reused without loss of efficiency. The presence of tin residues in halogenated aromatic amines was also investigated and evaluated at under 20 ppm after three runs.
Chretien, Jean-Mathieu,Zammattio, Francoise,Le Grognec, Erwan,Paris, Michael,Cahingt, Blanche,Montavon, Gilles,Quintard, Jean-Paul
p. 2870 - 2873
(2007/10/03)

Effective and regioselective iodination of arenes using iron(III) nitrate in the presence of tungstophosphoric acid
An easy, cheap, and effective method for iodination of various aromatic compounds takes place with molecular iodine and iron nitrate nonahydrate as the oxidant in the presence of a catalytic amount of tungstophosphoric acid in dichloromethane, with good yield and high regioselectivity under very mild conditions.
Jafarzadeh, Mohammad,Amani, Kamal,Nikpour, Farzad
p. 1808 - 1811
(2007/10/03)

Synthesis of terphenyl oligomers as molecular electronic device candidates
Six functionalized bis(phenylene ethynylene)-p,p-terphenyls (BPETs) have been synthesized as potential molecular electronic devices. The molecules containing mono- and dinitro terphenyl cores, were rationally designed based on the electronic properties recently found in oligo(phenylene ethynylene)s (OPEs). From our understanding of the conductance properties in OPEs, improvement of electronic properties may be possible by using BPETs due to a higher rotational barrier between the central aromatic rings of the compounds prepared here. BPETs cores were functionalized with nitro groups and with different metallic adhesion moieties (alligator clips) to provide new compounds for testing in the nanopore and planar testbed structures.
Maya, Francisco,Tour, James M.
p. 81 - 92
(2007/10/03)

Improved and new syntheses of potential molecular electronics devices
New syntheses of ethyl and nitro substituted oligo(phenylene ethynylene)s (OPEs) have been developed. To further explore whether the presence of nitro functionality in OPEs leads to switching and memory capabilities, new nitro substituted OPEs have been designed and synthesized. An isatogen-based system, a structure that is isomeric to the nitro OPE, has been synthesized. Additionally, pyridine-based and chromium-based compounds have been synthesized. We surmise that redox reactions of these candidates may impart switching capabilities and electrochemical studies are shown. U-shaped OPEs were synthesized to inhibit leakage of metals deposited during formation of top contacts on self-assembled monolayers (SAMs). The OPEs contain either thiol-based moieties or isonitrile groups to enable formation of SAMs on metal substrates.
Price Jr., David W.,Dirk, Shawn M.,Maya, Francisco,Tour, James M.
p. 2497 - 2518
(2007/10/03)

Biphenyl- and fluorenyl-based potential molecular electronic devices
New potential molecular electronics devices have been synthesized based on our knowledge of systems that we previously studied. Research has shown that simple molecular systems demonstrate negative differential resistance (NDR) and memory characteristics. The new molecules rely primarily on the redox properties of the compounds to improve upon the solid-state characteristics already observed. Electrochemical tests have been performed in order to evaluate the redox properties with the hope that the electrochemical results can be used as a predictive tool to evaluate the usefulness of those compounds in device configurations.
Price Jr., David W.,Tour, James M.
p. 3131 - 3156
(2007/10/03)

Preparation and antifungal activity of 3-Iodo- and 6-Iodo-8-quinolinols
3-Iodo- and 6-Iodo-8-quinolinols were prepared and tested against six fungi: Aspergillus niger, A. oryzae, Myrothecium verrucaria, Trichoderma viride, Mucor cirinelloides, and Trichophyton mentagrophytes in Sabouraud dextrose broth. A comparison with the previously known 5-iodo- and 7-iodo-8-quinolinols showed that the 6-iodo isomer was the most active.
Gershon, Herman,Clarke, Donald D.,McMahon, John J.,Gershon, Muriel
p. 1325 - 1330
(2007/10/03)

Interplay of hydrogen bonds, iodo nitro interactions and aromatic π...π stacking interactions in iodo-nitroanilines
Molecules of 2-iodo-5-nitroaniline (I) are linked by N-H...O hydrogen bonds into centrosymmetric dimers and by asymmetric three-centre iodo...nitro interactions into chains, so forming chains of fused centrosymmetric rings: these chains are linked by aromatic π...π stacking interactions to form a three-dimensional structure. In the isomeric 4-iodo-2-nitro-aniline (II), each of the two independent molecules forms hydrogen-bonded chains that are linked by two-centre iodo...nitro interactions into sheets of two types, each containing only a single type of molecule: π...π stacking interactions are absent. In 2,4-diiodo-3-nitroaniline (III), where the nitro group is almost orthogonal to the aryl ring, a combination of N - H...O hydrogen bonds and two distinct two-centre iodo...nitro interactions links the molecules into a three-dimensional framework that is reinforced by aromatic π...π stacking interactions. Bond lengths and conformations are discussed and comparisons are drawn with related compounds.
Garden, Simon J.,Fontes, Silvia P.,Wardell, James L.,Skakle, Janet M. S.,Low, John N.,Glidewell, Christopher
p. 701 - 709
(2007/10/03)

Oxidative Iodination of Aromatic Amides Using Sodium Perborate or Hydrogen Peroxide with Sodium Tungstate
Hydrogen peroxide or sodium perborate in the presence of a sodium tungstate catalyst are shown to be cheap oxidants for the iodination of aromatic amides using potassium iodide as the source of the iodine.
Beinker, Philipp,Hanson, James R.,Meindl, Nadja,Rodriguez Medina, Inmaculada C.
p. 204 - 205
(2007/10/03)

1,1,1-trimethylhydrazinium iodide: A novel, highly reactive reagent for aromatic amination via vicarious nucleophilic substitution of hydrogen
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Pagoria, Philip F.,Mitchell, Alexander R.,Schmidt, Robert D.
p. 2934 - 2935
(2007/10/03)

Glycine receptor antagonists and the use thereof
Methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions, inducing anesthesia and treating psychosis are disclosed by administering to an animal in need of such treatment a compound having high affinity for the glycine binding site, lacking PCP side effects and which crosses the blood brain barrier of the animal. Also disclosed are novel 1,4-dihydroquinoxaline-2,3-diones, and pharmaceutical compositions thereof. Also disclosed are highly soluble ammonium salts of 1,4-dihydroquinoxaline-2,3-diones.
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(2008/06/13)

Acid-Mediated Reaction of Bis(pyridine)iodonium(I) Tetrafluoroborate with Aromatic Compounds. A Selective and General Iodination Method
Reaction of aromatic compounds with bis(pyridine)iodonium(I) tetrafluoroborate (IPy2BF4) in the presence of HBF4 or CF3SO3H in CH2Cl2 at room temperature furnishes monoiodo derivatives with excellent regioselectivity and yields.Use of either acid gives comparable results with activated aromatics, whereas CF3SO3H is much more effective in the iodination of deactivated aromatics.
Barluenga, Jose,Gonzalez, Jose M.,Garcia-Martin, Miguel A.,Campos, Pedro J.,Asensio, Gregorio
p. 2058 - 2060
(2007/10/02)

Iodination of aromatic amines with iodine and silver sulfate
Iodination of aromatic amines with iodine/silver sulfate at room temperature gives iodo-products in good (46-96%) yield.
Sy
p. 3215 - 3219
(2007/10/02)

Iminodiacetic acid derivatives of benzimidazole. Synthesis of N-(benzimidazol)-2-ylmethyl)iminodiacetic acids
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Wilson,Hunt
p. 2317 - 2325
(2007/10/02)