Category: iodides-buliding-blocks

Oxalic Diamides and tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction was written by Chen, Zhixiang;Jiang, Yongwen;Zhang, Li;Guo, Yinlong;Ma, Dawei. And the article was included in Journal of the American Chemical Society in 2019.HPLC of Formula: 5460-32-2 This article mentions the following:

A robust and practical protocol for preparing alkyl aryl ethers has been developed, which relies on using two types of ligands to promote Cu-catalyzed alkoxylation of (hetero)aryl halides. The reaction scope is very general for a variety of coupling partners, particularly for challenging secondary alcs. and (hetero)aryl chlorides. In case of coupling with aryl chlorides and bromides, two oxalic diamides serve as the powerful ligands. The tert-butoxide is first demonstrated as a ligand for Cu-catalyzed coupling reaction, leading to alkoxylation of aryl iodides complete at room temperature Addnl., a number of carbohydrate derivatives are applicable for this coupling reaction, affording the corresponding carbohydrate-aryl ethers in 29-98% yields. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2HPLC of Formula: 5460-32-2).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) 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.HPLC of Formula: 5460-32-2

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

Discovery of imidazoleisoindole derivatives as potent IDO1 inhibitors: Design, synthesis, biological evaluation and computational studies was written by Zou, Yi;Wang, Fang;Wang, Yan;Sun, Qirui;Hu, Yue;Li, Yuezhen;Liu, Wen;Guo, Wenjie;Huang, Zhangjian;Zhang, Yihua;Xu, Qiang;Lai, Yisheng. And the article was included in European Journal of Medicinal Chemistry in 2017.Product Details of 15813-09-9 This article mentions the following:

Indoleamine-2,3-dioxygenase-1 (IDO1) is an attractive target for cancer immunotherapy. Herein, a series of novel imidazoleisoindole derivatives were prepared and evaluated for their ability to inhibit IDO1. Among these, derivative 11r was the most active compound with nanomolar potency in the Hela cell-based assay, while showed negligible cellular toxicity. UV-visible spectra study demonstrated that compounds 11p and 11r bound to IDO1 and coordinated with the heme iron. Furthermore, they could significantly promote T cell proliferation, increase IFN-γ production, and reduce the numbers of Foxp3⁺ regulatory T cells. Finally, induced fit docking (IFD) and quantum mechanics/mol. mechanics (QM/MM) calculation were performed to understand the interactions of these compounds to IDO1 protein, which provided a comprehensive guide for further structural modification and optimization. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Product Details of 15813-09-9).

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. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Product Details of 15813-09-9

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

A novel Apigenin derivative suppresses renal cell carcinoma via directly inhibiting wild-type and mutant MET was written by Li, Jing;Tan, Guishan;Cai, Yabo;Liu, Ruihuan;Xiong, Xiaolin;Gu, Baohua;He, Wei;Liu, Bing;Ren, Qingyun;Wu, Jianping;Chi, Bo;Zhang, Hang;Zhao, Yanzhong;Xu, Yangrui;Zou, Zhenxing;Kang, Fenghua;Xu, Kangping. And the article was included in Biochemical Pharmacology (Amsterdam, Netherlands) in 2021.Reference of 2314-37-6 This article mentions the following:

MET, the receptor of hepatocyte growth factor (HGF), is a driving factor in renal cell carcinoma (RCC) and also a proven drug target for cancer treatment. To improve the activity and to investigate the mechanisms of action of Apigenin (APG), novel derivatives of APG with improved properties were synthesized and their activities against Caki-1 human renal cancer cell line were evaluated. It was found that compound 15e exhibited excellent potency against the growth of multiple RCC cell lines including Caki-1, Caki-2 and ACHN and is superior to APG and Crizotinib. Subsequent investigations demonstrated that compound 15e can inhibit Caki-1 cell proliferation, migration and invasion. Mechanistically, 15e directly targeted the MET kinase domain, decreased its auto-phosphorylation at Y1234/Y1235 and inhibited its kinase activity and downstream signaling. Importantly, 15e had inhibitory activity against mutant MET V1238I and Y1248H which were resistant to approved MET inhibitors Cabozantinib, Crizotinib or Capmatinib. In vivo tumor graft study confirmed that 15e repressed RCC growth through inhibition of MET activation. These results indicate that compound 15e has the potential to be developed as a treatment for RCC, and especially against drug-resistant MET mutations. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Reference of 2314-37-6).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) 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. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Reference of 2314-37-6

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

Radical Hydrodeiodination of Aryl, Alkenyl, Alkynyl and Alkyl Iodides with an Alcoholate as Organic Chain Reductant through Electron Catalysis was written by Dewanji, Abhishek;Mueck-Lichtenfeld, Christian;Studer, Armido. And the article was included in Angewandte Chemie, International Edition in 2016.HPLC of Formula: 77350-52-8 This article mentions the following:

A simple and efficient method for radical hydrodeiodination is reported. The novel approach uses electron catalysis. In situ generated Na-alcoholates are introduced as radical chain reducing reagents and reactions work with O₂ as cheap initiator. Hydrodeiodination works on aryl, alkenyl, alkynyl iodides and a tert-alkyl iodide also gets reduced applying the method. Albeit less general, the method is also applicable to the reduction of aryl bromides. The novel reagent is successfully used to conduct typical reductive radical cyclization reactions and mechanistic studies are reported. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8HPLC of Formula: 77350-52-8).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.HPLC of Formula: 77350-52-8

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

Controllable synthesis of pyrido[2,3-b]indol-4-ones or indolo[3,2-b]quinolines via formal intramolecular C(sp²)-H functionalization was written by Song, Bo;Wang, Mengdan;Xu, Murong;Kong, Lingkai;Xie, Huihui;Wang, Chengyu;Li, Yanzhong. And the article was included in Organic & Biomolecular Chemistry in 2019.Application In Synthesis of 4-Chloro-2-iodo-1-nitrobenzene This article mentions the following:

A novel Fe-catalyzed protocol for the controllable synthesis of pyrido[2,3-b]indol-4-ones or indolo[3,2-b]quinolines was developed by using indole-2-carboxylic derivatives as starting materials. Indole-2-carboxenamines were transformed into pyrido[2,3-b]indol-4-ones through intramol. N-H/C-H coupling, in which a carbonyl 1,2-migration was involved. Whereas, when indole-2-carboxarylamines were employed, indolo[3,2-b]quinolones were produced through direct N-H/C-H coupling. The desired products were obtained under mild reaction conditions in moderate to good yields with wide substrate scope. The natural product quindolinone was conveniently prepared by this reaction. In the experiment, the researchers used many compounds, for example, 4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1Application In Synthesis of 4-Chloro-2-iodo-1-nitrobenzene).

4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Application In Synthesis of 4-Chloro-2-iodo-1-nitrobenzene

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

Five-component trigonal nanoprism with six dynamic corners was written by Gaikwad, Sudhakar;Lal Saha, Manik;Samanta, Debabrata;Schmittel, Michael. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2017.Recommanded Product: 1,4-Diiodo-2,3,5,6-tetramethylbenzene This article mentions the following:

The metallo-supramol. trigonal prism P is based on five different components and three unlike dynamic coordination motifs: the heteroleptic phenanthroline-terpyridine complex [Zn(1)(4)]²⁺ (HETTAP), the heteroleptic phenanthroline-pyridine complex [Cu(2)(5A)]⁺ (HETPYP-I), and the pyridine → zinc(II)-porphyrin interaction. In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1Recommanded Product: 1,4-Diiodo-2,3,5,6-tetramethylbenzene).

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. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.Recommanded Product: 1,4-Diiodo-2,3,5,6-tetramethylbenzene

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

Continuous flow synthesis of the iodination agent 1,3-diiodo-5,5-dimethyl-imidazolidine-2,4-dione telescoped with semi-continuous product isolation was written by Ferreri, Marta;Drageset, Audun;Gambarotti, Cristian;Bjoersvik, Hans-Rene. And the article was included in Reaction Chemistry & Engineering in 2016.Synthetic Route of C3H2I2N2 This article mentions the following:

A batch synthesis to the iodinating agent 1,3-diiodo-5,5-dimethyl-imidazolidine-2,4-dione (DIH) was devised and developed. This batch process was then up-scaled (10x) and optimized by means of statistical exptl. design and multivariate regression. The optimized batch procedure was then transferred and adapted for continuous flow synthesis using a multi-jet oscillating disk (MJOD) continuous flow reactor platform to provide a flow process that allowed a throughput of 47 g h^-1 with a residence time of 9 min. A semi-continuous work-up step based on vacuum filtration was established and successfully telescoped to be an integrated part of the flow process. An 8 h test run using the optimized flow synthesis in combination with the semi-continuous filtration step afforded 375 g (̃ 90% isolated yield) of the pure title compound that was collected from 14 filtration batches of 25-27 g each. 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. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.Synthetic Route of C3H2I2N2

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

Versatile Palladium-Catalyzed Approach to Acyl Fluorides and Carbonylations by Combining Visible Light- and Ligand-Driven Operations was written by Liu, Yi;Zhou, Cuihan;Jiang, Meijing;Arndtsen, Bruce A.. And the article was included in Journal of the American Chemical Society in 2022.Application of 10297-05-9 This article mentions the following:

The development of a general palladium-catalyzed carbonylative method to synthesize acyl fluorides RC(O)F (R = n-Bu, cyclohexyl, 4-methylphenyl, pyridin-3-yl, etc.) from aryl, heteroaryl, alkyl, and functionalized organic halides RX was described. Mechanistic anal. suggests that the reaction proceeds via the unique, synergistic combination of visible light photoexcitation of Pd(0) to induce oxidative addition with a ligand-favored reductive elimination. These together create a unidirectional catalytic cycle that is uninhibited by the classical effect of carbon monoxide coordination. Coupling the catalytic formation of acyl fluorides with their subsequent nucleophilic reactions has opened a method to perform carbonylation reactions with unprecedented breadth, including the assembly of highly functionalized carbonyl-containing products. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Application of 10297-05-9).

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. 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.Application of 10297-05-9

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

A unified synthetic strategy for the indolopyridine alkaloid group was written by Lavilla, Rodolfo;Gullon, Francisco;Bosch, Joan. And the article was included in European Journal of Organic Chemistry in 1999.Synthetic Route of C6H4INO2 This article mentions the following:

Thermal or AcCl-induced cyclization of bromo enamide I (R, R¹ = H; R² = Br) 10 affords the pentacyclic derivative I (RR¹ = bond, R² = Br) 12 with high yield and regioselectivity. From this common synthetic intermediate, Pd-catalyzed reactions allow the total synthesis of indolopyridine alkaloids I (RR¹ = bond; R² = CH:CH₂, Et, Ac, CHMeOMe). In the experiment, the researchers used many compounds, for example, 5-Iodonicotinic acid (cas: 15366-65-1Synthetic Route of C6H4INO2).

5-Iodonicotinic acid (cas: 15366-65-1) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Synthetic Route of C6H4INO2

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

5-Chloro- and 5,6-dichloronicotinic acids was written by Graf, Roderich;Lederer-Ponzer, Ernst;Kopetz, Viktor;Purkert, Renato;Laszlo, Paul. And the article was included in Journal fuer Praktische Chemie (Leipzig) in 1933.HPLC of Formula: 15366-65-1 This article mentions the following:

Nicotinic acid HCl salt (100 g.) and 180 g. SOCl₂, gently boiled 5 days and then heated in tubes 12 hrs. at 180°, give 50-60% of a mixture of the 5-Cl and 5,6-di-Cl derivatives (I), in about equal amounts; more SOCl₂ increases the proportion of the di-Cl acid. 5-Aminopyridine-3-carboxylic acid (II), m. 288-90° (decomposition). II through the diazo reaction gives the 5-Br derivative, m. 182-3°; chloride, m. 74-5°; Me ester, m. 98-9°; Ph ester, m. 86-7°. The chloride and N₂H₄.H₂O in C₆H₆ give sym-bis(5-bromo-3-pyridoyl)hydrazine, m. 308° (decomposition). The Me ester gives 5-bromopyridine-3-carbonyl hydrazide, m. 193-4° (benzal derivative, m. 191-3°); the azide m. 88-9° (decomposition) and with absolute EtOH gives 5-bromo-3-carbethoxyaminopyridine, m. 150-1°; Me ester, m. 169-70°; heating the Et ester with 30% NaOH gives 5-bromo-3-aminopyridine (III), b₁₂ 149-50°, m. 66-7°; the intermediate Na 5-bromo-3-pyridylcarbamate was also analyzed; Ac derivative of III, m. 127-8° (dihydrate, m. 76-8°); picrate of III, deep yellow, m. 212-3°; chloroaurate, red-orange, m. 185-7°. 5-Iodopyridine-3-carboxylic acid, m. 220°; Ph ester, m. 100-1° Me ester, m. 121°; Et ester, m. 86-7°; amide, m. 221-2°. 5-Hydroxypyridine-3-carboxylic acid, m. 299° (decomposition). The Et ester of I and N₂H₄.H₂O give Et 5-chloro-6-hydrazinopyridine-3-carboxylate (IV), m. 137-8°; the hydrazide, gray, m. 238-40°; the free acid m. 248-9° and was also obtained directly from I. IV on diazotizing yields Et 5-chlorobenzotetrazole-3-carboxylate, m. 95-6°; the free acid m. 195-6°; heating with HCO₂H gives 5-chlorobenzotriazole-3-carboxylic acid, m. above 300°. I and concentrated NH₄OH at 180-90° give 6-amino-5-chloropyridine-3-carboxylic acid, m. 323° (decomposition); Me ester, m. 163-5°; the Me ester of the 6-HO derivative m. 218°. In the experiment, the researchers used many compounds, for example, 5-Iodonicotinic acid (cas: 15366-65-1HPLC of Formula: 15366-65-1).

5-Iodonicotinic acid (cas: 15366-65-1) 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. 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.HPLC of Formula: 15366-65-1

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