Category: iodides-buliding-blocks

C-H functionalization of N-methylated amino acids and peptides as tool in natural product synthesis: Synthesis of Abyssenine A and Mucronine E was written by Kinsinger, Thorsten;Kazmaier, Uli. And the article was included in Organic Letters in 2018.Electric Literature of C8H7IO2 This article mentions the following:

N-Methylated amino acids and peptides with an 8-aminoquinoline (AQ) directing group can be subjected to stereoselective Pd-catalyzed β-functionalizations. The best results are obtained with aryl iodides, but alkyl and alkenyl side chains can also be introduced. The AQ protecting group can easily be removed, providing the free carboxylic acid, which can be used directly in peptide couplings. This protocol was used successfully as a key step in the synthesis of the cyclopeptide alkaloids abyssenine A and mucronine E. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Electric Literature of C8H7IO2).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. 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.Electric Literature of C8H7IO2

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

Design of PAP-1, a selective small molecule Kv1.3 blocker, for the suppression of effector memory T cells in autoimmune diseases was written by Schmitz, Alexander;Sankaranarayanan, Ananthakrishnan;Azam, Philippe;Schmidt-Lassen, Kristina;Homerick, Daniel;Haensel, Wolfram;Wulff, Heike. And the article was included in Molecular Pharmacology in 2005.Application of 10297-05-9 This article mentions the following:

The lymphocyte K⁺ channel Kv1.3 constitutes an attractive pharmacol. target for the selective suppression of terminally differentiated effector memory T (T_EM) cells in T cell-mediated autoimmune diseases, such as multiple sclerosis and type 1 diabetes. Unfortunately, none of the existing small-mol. Kv1.3 blockers is selective, and many of them, such as correolide, 4-phenyl-4-[3-(methoxyphenyl)-3-oxo-2-azapropyl]cyclohexanone, and our own compound Psora-4 inhibit the cardiac K⁺ channel Kv1.5. By further exploring the structure-activity relationship around Psora-4 through a combination of traditional medicinal chem. and whole-cell patch-clamp, we identified a series of new phenoxyalkoxypsoralens that exhibit 2- to 50-fold selectivity for Kv1.3 over Kv1.5, depending on their exact substitution pattern. The most potent and “drug-like” compound of this series, 5-(4-phenoxybutoxy)psoralen (PAP-1), blocks Kv1.3 in a use-dependent manner, with a Hill coefficient of 2 and an EC₅₀ of 2 nM, by preferentially binding to the C-type inactivated state of the channel. PAP-1 is 23-fold selective over Kv1.5, 33- to 125-fold selective over other Kv1-family channels, and 500- to 7500-fold selective over Kv2.1, Kv3.1, Kv3.2, Kv4.2, HERG, calcium-activated K⁺ channels, Na⁺, Ca²⁺, and Cl^– channels. PAP-1 does not exhibit cytotoxic or phototoxic effects, is neg. in the Ames test, and affects cytochrome P 450-dependent enzymes only at micromolar concentrations PAP-1 potently inhibits the proliferation of human T_EM cells and suppresses delayed type hypersensitivity, a T_EM cell-mediated reaction, in rats. PAP-1 and several of its derivatives therefore constitute excellent new tools to further explore Kv1.3 as a target for immunosuppression and could potentially be developed into orally available immunomodulators. 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. 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.Application of 10297-05-9

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

Cu-catalyzed decarboxylative iodination of aryl carboxylic acids with NaI: A practical entry to aryl iodides under aerobic conditions was written by Fu, Zhengjiang;Jiang, Yongqing;Jiang, Ligao;Li, Zhaojie;Guo, Shengmei;Cai, Hu. And the article was included in Tetrahedron Letters in 2018.Recommanded Product: 4-Chloro-2-iodo-1-nitrobenzene This article mentions the following:

A simple and practical Cu-catalyzed decarboxylative iodination has been well established under aerobic condition, which provides a useful method to synthesize aryl iodides in moderate to good yields with the use of (hetero)aryl carboxylic acids and NaI as starting materials [e.g., 4-chloro-2-nitrobenzoic acid â†?4-chloro-1-iodo-2-nitrobenzene (80%) using NaI in presence of Cu(OAc)₂, 1,10-Phen and O₂ in DMSO]. Thiabendazole has been prepared via a three-step procedure to show synthetic practicability of the protocol. In the experiment, the researchers used many compounds, for example, 4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1Recommanded Product: 4-Chloro-2-iodo-1-nitrobenzene).

4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. 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.Recommanded Product: 4-Chloro-2-iodo-1-nitrobenzene

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

Distannane mediated reaction of N-acyliminium ion pools with alkyl halides. A chain mechanism involving radical addition followed by electron transfer was written by Maruyama, Tomokazu;Suga, Seiji;Yoshida, Jun-ichi. And the article was included in Tetrahedron in 2006.Recommanded Product: 10297-05-9 This article mentions the following:

Hexabutyldistannane is an effective mediator allowing the reaction of N-acyliminium ion pools with alkyl halides. A chain mechanism involving the addition of an alkyl radical generated from an alkyl halide to an N-acyliminium ion followed by the 1-electron reduction of the resulting radical-cation by distannane was proposed. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Recommanded Product: 10297-05-9).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. 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.Recommanded Product: 10297-05-9

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

Reductive Hydroxymethylation of 4-Heteroarylpyridines was written by Hepburn, Hamish B.;Donohoe, Timothy J.. And the article was included in Chemistry – A European Journal in 2020.COA of Formula: C4H8ClI This article mentions the following:

The activation of pyridinium salts with electron-withdrawing heterocycles enabled an iridium-catalyzed reductive hydroxymethylation reaction to proceed smoothly, facilitating the preparation of useful 3D heteroaryl-substituted functionalized piperidines. The methodol. was used to prepare 3-hydroxymethylated analogs of pharmaceutical agents. Mechanistically, formaldehyde acts as both a hydride donor and the electrophile, leading to the formation of two new carbon-hydrogen bonds and one new carbon-carbon bond under relatively mild conditions. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9COA of Formula: C4H8ClI).

1-Chloro-4-iodobutane (cas: 10297-05-9) 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.COA of Formula: C4H8ClI

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

Efficient copper-catalyzed amination of DNA-conjugated aryl iodides under mild aqueous conditions was written by Ruff, Yves;Berst, Frederic. And the article was included in MedChemComm in 2018.Recommanded Product: 5-Iodonicotinic acid This article mentions the following:

Herein, we describe the development of copper-catalyzed cross-coupling of DNA-conjugated aryl iodides with aliphatic amines. This protocol leverages a novel ligand, 2-((2,6-dimethoxyphenyl)amino)-2-oxoacetic acid, to effect the transformation in aqueous DMSO, under mild conditions and in air, making it an ideal candidate for the synthesis of DNA-encoded libraries. In the experiment, the researchers used many compounds, for example, 5-Iodonicotinic acid (cas: 15366-65-1Recommanded Product: 5-Iodonicotinic acid).

5-Iodonicotinic acid (cas: 15366-65-1) 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. 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.Recommanded Product: 5-Iodonicotinic acid

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

ortho-Metalation of Unprotected 3-Bromo and 3-Chlorobenzoic Acids with Hindered Lithium Dialkylamides was written by Gohier, Frederic;Mortier, Jacques. And the article was included in Journal of Organic Chemistry in 2003.Related Products of 123278-03-5 This article mentions the following:

Upon treatment of 3-chloro/bromobenzoic acids with hindered lithium dialkylamides (LDA or LTMP) at -50 °C, lithium 3-chloro/bromo-2-lithiobenzoates are generated. These dianions can be trapped as such to afford after electrophilic quenching a variety of simple 2-substituted-3-chloro/bromobenzoic acids. The 3-bromo-2-lithiobenzoate is less stable than the 3-chloro analog and partly eliminates lithium bromide, thus setting free lithium 2,3- and 3,4-dehydrobenzoates that can be intercepted in situ with the hindered base. In the experiment, the researchers used many compounds, for example, 3-Chloro-2-iodobenzoic acid (cas: 123278-03-5Related Products of 123278-03-5).

3-Chloro-2-iodobenzoic acid (cas: 123278-03-5) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. 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.Related Products of 123278-03-5

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

Palladium-catalyzed cyanation of aryl halides with in situ generated CN^– from ClCF₂H and NaNH₂ was written by Yu, Changjiang;Ma, Xingxing;Song, Qiuling. And the article was included in Organic Chemistry Frontiers in 2020.Synthetic Route of C8H9IO2 This article mentions the following:

An efficient Pd-catalyzed cyanation of aryl halides with in situ generated CN^– anions is described. The CN^– source stems from the quadruple cleavage of chlorodifluoromethane (ClCF₂H) with sodium amide (NaNH₂). This transformation features no requirement of a toxic CN source and avoids the problem of HCN generation associated with traditional methods. A series of aryl nitriles are obtained from aryl halides in good yields under mild reaction conditions. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Synthetic Route of C8H9IO2).

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. 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 C8H9IO2

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

Palladium-catalyzed aminocarbonylation in solid-phase peptide synthesis: A method for capping, cyclization, and isotope labeling was written by Skogh, Anna;Friis, Stig D.;Skrydstrup, Troels;Sandstroem, Anja. And the article was included in Organic Letters in 2017.Electric Literature of C8H9IO2 This article mentions the following:

A new synthetic approach for introducing N-capping groups onto peptides attached to a solid support, combining aminocarbonylation under mild conditions using a palladacycle precatalyst and solid-phase peptide synthesis, is reported. The use of a silacarboxylic acid as an in situ CO-releasing mol. allowed the reaction to be performed in a single vial. The method also enables versatile substitution of side chains, side-chain-to-side-chain cyclizations, and selective [¹³C] acyl labeling of modified peptides. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Electric Literature of C8H9IO2).

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. 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.Electric Literature of C8H9IO2

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

The Palladium Slow-Release Pre-Catalysts and Nanoparticles in the “Phosphine-Free” Mizoroki-Heck and Suzuki-Miyaura Reactions was written by Sigeev, Alexander S.;Peregudov, Alexander S.;Cheprakov, Andrei V.;Beletskaya, Irina P.. And the article was included in Advanced Synthesis & Catalysis in 2015.Reference of 5460-32-2 This article mentions the following:

The Mizoroki-Heck reaction of electron-rich aryl iodides was studied using a phosphine-free catalytic system with a broad range of pre-catalysts of varied stability and structure based on organoselenium chelators. The application of the Hg test by observing the response of the catalytic systems studied not only to the addition, but also to the withdrawal of Hg allowed the authors to establish a critical role of nanoparticles in the operation of the phosphine-free catalytic systems. A three-stage mechanistic scheme involving a slow stage served by mononuclear Pd species, and the main fast stage served by Pd nanoparticles, and terminated by the nanoparticle decay is proposed as a general mechanistic paradigm for the phosphine-free Mizoroki-Heck and the related Suzuki-Miyaura reactions. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Reference of 5460-32-2).

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

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