Category: iodides-buliding-blocks

Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylsulfonium halides generated in situ was written by Baik, Woonphil;Luan, Wanqiang;Lee, Hyun Joo;Yoon, Cheol Hun;Koo, Sangho;Kim, Byeong Hyo. And the article was included in Canadian Journal of Chemistry in 2005.Related Products of 160938-18-1 This article mentions the following:

Halodimethylsulfonium halides, which were readily formed in situ from hydrohalic acids and DMSO, was a good nucleophilic halide. This activated nucleophilic halide rapidly converted aryldiazonium salt prepared in situ by the same hydrohalic acid and nitrite ion to aryl chlorides, bromides, or iodides in good yield. The combined action of nitrite ion and hydrohalic acid in DMSO was required for the direct transformation of aromatic amines, which resulted in the production of aryl halides. Substituted compounds with electron-donating or -withdrawing groups or sterically hindered aromatic amines were also smoothly transformed to the corresponding aromatic halides. The only observed byproduct was the deaminated arene. The isolated aryldiazonium salts can also be converted to the corresponding aryl halides using the halodimethylsulfonium halides. The present method offers a facile, one-step procedure for transforming aminoarenes to haloarenes and lacks the environmental pollutants that usually accompany the Sandmeyer reaction using copper halides. In the experiment, the researchers used many compounds, for example, 4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1Related Products of 160938-18-1).

4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1) belongs to iodide derivatives. Organic iodides are organic compounds containing a carbon-iodine (C-I) bond. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.Related Products of 160938-18-1

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Modular synthesis of helicene-like compounds based on the imidazolium motif was written by Cizkova, Martina;Saman, David;Koval, Dusan;Kasicka, Vaclav;Klepetarova, Blanka;Cisarova, Ivana;Teply, Filip. And the article was included in European Journal of Organic Chemistry in 2014.Synthetic Route of C3H2I2N2 This article mentions the following:

Straightforward synthesis of novel mono- and tricationic helical compounds based on the imidazolium core was developed. The synthetic route based on double [2+2+2] cycloaddition reactions of precursors with the imidazolium core motif is notably modular and reaches beyond established protocols used for the synthesis of imidazolium systems as well as beyond the reported protocols used to assemble compounds with helical frameworks. This approach opened rapid four-step access to a cationic species featuring nine ortho-annulated rings that represents the highest order helical nitrogen-based cationic system reported to date. The structure of 2 was confirmed by the single crystal x-ray diffraction anal. [monoclinic, space group C2/c, a 39.389(3), b 14.2400(12), c 17.8968(14) Å, β 114.276(3)°, V 9150.7(13) ų, Z 8]. The detailed crystallog. data were deposited at the Cambridge Crystallog. Data Center as supplementary publication number CCDC 955735. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Synthetic Route of C3H2I2N2).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.Synthetic Route of C3H2I2N2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The direct iodination of polyalkylbenzenes bearing bulky groups was written by Suzuki, Hitomi;Nakamura, Kiyomi;Goto, Ryozo. And the article was included in Bulletin of the Chemical Society of Japan in 1966.COA of Formula: C10H12I2 This article mentions the following:

A number of polyalkylbenzenes, bearing bulky substituents, afforded mono-iodo derivatives in high yield when treated with iodine-HIO₄. HIO₄ proved to be the most effective of several oxidizing agents examnd.: Ag₂SO₄, AgClO₄, HgO, K₂S₂O₈, HIO₃, and ο-IC₆H₄OMe. The reaction also proceded smoothly to yield mono- and diiodo derivatives of some polymethylbenzenes, but tri- and tetraiodination of xylene was difficult to effect. In a typical preparation a mixture of 5.40 g. 5-tert-Bu-1,3-Me₂C₆H₃, 1.54 g. HIO₄.2H₂O, 3.39 g. iodine, and 20 ml. 10:2:0.3 AcOH-H₂O-H₂SO₄ was stirred 4 hrs. at 60-5°. The mixture was cooled and the solid product was crystallized from petr. ether to give 8.7 g. 4-tert-Bu-2,6-Me₂C₆H₂I, m. 59-60°. The iodine atom was assumed to enter the ring para to the tert-Bu group. A similar procedure afforded the following compounds in good yield (compound, reaction time, reaction temperature, m.p., and b.p./mm. given): 5-tert-Bu-2,3-Me₂C₆H₂I, 6-7 hrs., 60-5°,–, 146-7°/14; 6-tert-Bu-2,3,4-Me₃C₆HI, 6-7 hrs., 60-5°, 74-5°,–; 2,3,5,6-iso-Pr₄C₆HI, 30 hrs., 75-80°, 161-3°,–; 2,5-tert-Bu₂C₆H₃I, ∼30 hrs., 75-80°,–, 156-7°/13-14; 4,5-I₂-1,2-Me₂C₆H₂, 3-4 hrs., 70°, 93-4°,–; 2,5-I₂-1,4-Me₂C₆H₂, 3-4 hrs., 70°, 104-5°,–; diiodoprehnitene, 1.5 hrs., 70°, 190-1°,–; diiododurene, 1.5 hrs., 70°, 140-1°,–. Where necessary, compounds were purified by chromatography over alumina and structures were verified by ir spectral examination In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1COA of Formula: C10H12I2).

1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.COA of Formula: C10H12I2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Light-Up “Channel Dyes” for Haloalkane-Based Protein Labeling in Vitro and in Bacterial Cells was written by Clark, Spencer A.;Singh, Vijay;Vega Mendoza, Daniel;Margolin, William;Kool, Eric T.. And the article was included in Bioconjugate Chemistry in 2016.Synthetic Route of C4H8ClI This article mentions the following:

The authors describe a novel mol. strategy for engendering a strong light-up signal in fluorescence tagging of the genetically encoded HaloTag protein domain. The authors designed a set of haloalkane-derivatized dyes having twisted internal charge transfer (TICT) structures potentially narrow enough to partially fit into the enzyme’s haloalkane-binding channel. Testing a range of short chain lengths revealed a number of active dyes, with seven carbons yielding optimum light-up signal. The dimethylaminostilbazolium chloroheptyl dye (1d) yields a 27-fold fluorescence emission enhancement (λ_ex = 535 nm; Em_(max) = 616 nm) upon reaction with the protein. The control compound with standard 12-atom linkage shows less efficient signaling, consistent with the authors’ channel-binding hypothesis. For emission further to the red, the authors also prepared a chloroheptyl naphthalene-based dye; compound 2 emits at 653 nm with strong fluorescence enhancement upon reaction with the HaloTag domain. The two dyes (1d, 2) were successfully tested in wash-free imaging of protein localization in bacteria, using a HaloTag fusion of the filamenting temperature-sensitive mutant Z (FtsZ) protein in Escherichia coli (E. coli). The new dye conjugates are inexpensive and easily synthesized enzyme substrates with low background and large Stokes shifts, offering substantial benefits over known fluorescent substrates for the HaloTag enzyme. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Synthetic Route of C4H8ClI).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs.Synthetic Route of C4H8ClI

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Preparation and Diels-Alder Chemistry of 4-Vinylimidazoles was written by Lovely, Carl J.;Du, Hongwang;Rasapalli, Sivappa;Bhandari, Manojkumar R.;He, Yong;Dias, H. V. Rasika. And the article was included in Journal of Organic Chemistry in 2007.Category: iodides-buliding-blocks This article mentions the following:

Various 4-vinylimidazole derivatives have been prepared from the corresponding 4-iodoimidazoles or from urocanic acid. Several methods for the elaboration of these vinylimidazoles and their Diels-Alder reactions are reported. All of the vinylimidazoles prepared in the course of this study react with N-phenylmaleimide quite readily with mild thermal activation providing a single cycloadduct, in most cases the initial, nonaromatic adduct. With more electron rich substrates, there is a tendency for these initial cycloadducts to undergo aromatization, ene reaction, and oxidation although this can be circumvented to a large extent by the choice of reaction conditions. Limited reactions were observed with other dienophiles, providing the expected cycloadducts in most cases, although an abnormal adduct was obtained in one case with di-Me acetylene dicarboxylate. These substrates also participate in regioselective Diels-Alder reactions with monoactivated dienophiles, but require fairly forcing conditions, thus only providing the aromatized cycloadducts in modest yields. An investigation of substituent effects at the 2-position of the imidazole moiety was undertaken, in which electron-donating and weakly electron-withdrawing substituents are tolerated. In addition, several substrates with terminally substituted vinyl moieties have been investigated. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Category: iodides-buliding-blocks).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) belongs to iodide derivatives. Organic iodides are organic compounds containing a carbon-iodine (C-I) bond. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.Category: iodides-buliding-blocks

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthesis of 3-[4(5)-imidazolylmethyl]-2-methylbenzoic acid, a metabolite of the drug detomidine was written by Cardin, Christine J.;Convery, Maire A.;Kavanagh, Pierce V.;Lambert, Michael T. B.;McKenna, Brian;McMurray, T. Brian H.. And the article was included in Journal of Chemical Research, Synopses in 1992.Reference of 133232-56-1 This article mentions the following:

The synthesis of the title compound I (R = H, R¹ = CO₂H, X = H₂), a metabolite of detomidine I (R = H, R¹ = Me, X = H₂), is reported. A key step of the synthesis is the Grignard reaction of iodobenzyl alc. derivative II with 1-tritylimidazole-4-carboxaldehyde to give I (R = CPh₃, R¹ = CH₂OCH₂OMe, X = H, OH), which was converted in 6 steps to the title compound The crystal structure of I (R = H, R¹ = CO₂Me, X = H,H) was determined In the experiment, the researchers used many compounds, for example, 3-Iodo-2-methylbenzoic acid (cas: 133232-56-1Reference of 133232-56-1).

3-Iodo-2-methylbenzoic acid (cas: 133232-56-1) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.Reference of 133232-56-1

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Metal-Free Catalytic Asymmetric Fluorination of Keto Esters Using a Combination of Hydrogen Fluoride (HF) and Oxidant: Experiment and Computation was written by Pluta, Roman;Krach, Patricia E.;Cavallo, Luigi;Falivene, Laura;Rueping, Magnus. And the article was included in ACS Catalysis in 2018.Synthetic Route of C8H7IO4 This article mentions the following:

In the presence of nonracemic iodoarenes I [R = H, 3,5-(F₃C)₂C₆H₃], fused β-keto esters such as Et 1-oxo-2-indanecarboxylate underwent enantioselective fluorination with Et₃N·5 HF mediated by mCPBA in CHCl₃ to yield α-fluoro-β-keto esters such as II in 18-71% yields and in 83:17-96:4 er; thus, nucleophilic fluoride sources could be used as fluorinating reagents. The mechanism of the fluorination was studied using DFT calculations of transition states and intermediates and their free energies; attempted fluorination using a nonracemic aryliodine difluoride did not give fluorination product, indicating the importance of HF in the fluorination. In the experiment, the researchers used many compounds, for example, Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7Synthetic Route of C8H7IO4).

Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.Synthetic Route of C8H7IO4

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Selenium-catalyzed intramolecular atom- and redox-economical transformation of o-nitrotoluenes into anthranilic acids was written by Li, Yiming;Wang, Yuhong;Yang, Tilong;Lin, Zhenyang;Jiang, Xuefeng. And the article was included in Green Chemistry in 2021.COA of Formula: C7H6INO2 This article mentions the following:

Herein, a straightforward strategy to transform abundant o-nitrotoluenes into biol. and pharmaceutically significant AAs without any extra reductants, oxidants and protecting groups was demonstrated. Various sensitive groups, such as halogens, sulfide, aldehyde, pyridines, quinolines, etc., can be tolerated in this transformation. A hundred-gram-scale operation was realized efficiently with almost quant. selenium recycling. Further mechanistic studies and DFT calculations disclosed the proposed atom-exchange processes and the key roles of the selenium species. In the experiment, the researchers used many compounds, for example, 2-Amino-4-iodobenzoic acid (cas: 20776-54-9COA of Formula: C7H6INO2).

2-Amino-4-iodobenzoic acid (cas: 20776-54-9) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.COA of Formula: C7H6INO2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The reactivity of 2-fluoro- and 2-chloropyridines toward sodium ethoxide: Factors governing the rates of nucleophilic (het)aromatic substitutions was written by Schlosser, Manfred;Rausis, Thierry. And the article was included in Helvetica Chimica Acta in 2005.Electric Literature of C6H2ClF3IN This article mentions the following:

The relative displacement rates of the halide substituent from 2-fluoro- and 2-chloropyridines by EtONa in EtOH at +25° were assessed by competition kinetics. The 2-fluoropyridine reacts 320 times faster than the chloro analog. A CF₃ group increases the reactivity more than single halogen atoms do, whatever the element, and the latter are superior to Me₃Si groups. Substituents accommodated at the 4-position operate through their inductive effect, whereas at the 3-position, this action may be attenuated by steric hindrance. Almost all 5-substituents enhance the rate of the nucleophilic substitution occurring at the 2-position. The sole exception concerns the F-atom at the 5-position which retards the reaction, presumably by lone-pair/lone-pair repulsion with the neg. charge building up at the central C-atom of the intermediate Meisenheimer complex. The substituent effects are additive. Therefore, by using the increments derived from the present work, the rates of future reactions should be predictable with fair accuracy. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-(trifluoromethyl)-4-iodopyridine (cas: 505084-55-9Electric Literature of C6H2ClF3IN).

2-Chloro-5-(trifluoromethyl)-4-iodopyridine (cas: 505084-55-9) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.Electric Literature of C6H2ClF3IN

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Base- and Additive-Free Ir-Catalyzed ortho-Iodination of Benzoic Acids: Scope and Mechanistic Investigations was written by Erbing, Elis;Sanz-Marco, Amparo;Vazquez-Romero, Ana;Malmberg, Jesper;Johansson, Magnus J.;Gomez-Bengoa, Enrique;Martin-Matute, Belen. And the article was included in ACS Catalysis in 2018.Recommanded Product: 133232-56-1 This article mentions the following:

A protocol for the C-H activation/iodination of benzoic acids catalyzed by a simple iridium complex has been developed. The method described in this paper allows the ortho-selective iodination of a variety of benzoic acids under extraordinarily mild conditions in the absence of any additive or base in 1,1,1,3,3,3-hexafluoroisopropanol as the solvent. The iridium catalyst used tolerates air and moisture, and selectively gives ortho-iodobenzoic acids with high conversions. Mechanistic investigations revealed that an Ir(III)/Ir(V) catalytic cycle operates, and that the unique properties of HFIP enables the C-H iodination using the carboxylic moiety as a directing group. In the experiment, the researchers used many compounds, for example, 3-Iodo-2-methylbenzoic acid (cas: 133232-56-1Recommanded Product: 133232-56-1).

3-Iodo-2-methylbenzoic acid (cas: 133232-56-1) belongs to iodide derivatives. Organic iodides are widely used in organic synthesis. Halogenation of aromatic hydrocarbons is a very important reaction via an electrophilic aromatic substitution. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.Recommanded Product: 133232-56-1

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com