Category: iodides-buliding-blocks

Cross-Coupling of [2-Aryl-1,1,2,2-tetrafluoroethyl](trimethyl)silanes with Aryl Halides was written by O’Duill, Miriam;Dubost, Emmanuelle;Pfeifer, Lukas;Gouverneur, Veronique. And the article was included in Organic Letters in 2015.Synthetic Route of C8H9IO2 This article mentions the following:

The synthesis of arylCF₂CF₂SiMe₃ and their reactivity in cross-coupling reactions with aryl iodides and aryl bromides to afford a range of 1,1,2,2-tetrafluoro-1,2-diarylethanes is reported. The use of pyridine as an alternative to phenanthroline, and the ability to carry out the reaction at 60 °C or room temperature are the key features of this Cu-Ag mediated cross-coupling methodol. The chem. is compatible with (hetero)aryl halides, offering a platform to develop products of interest in material and medicinal chem. Thus, e.g, cross-coupling of silane I with aryl iodide II under optimized conditions consisting of CuI (1 equiv), AgF (1.5 equiv) and pyridine (5.0 equiv) in DMSO at 60° for 6 h afforded III (76%). 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 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.Synthetic Route of C8H9IO2

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

Synthesis and biological evaluation of a novel anti-malarial lead was written by Hammond, Nicholas L.;Choi, Seoung-ryoung;Carvalho, Paulo;Liu, Hua;Khan, Shabana;Avery, Mitchell A.. And the article was included in Medicinal Chemistry Research in 2011.Reference of 15813-09-9 This article mentions the following:

Malaria is re-emerging in many tropical areas of the world and is often fatal due to drug resistance, leading to about a million deaths each year. Multiple drug resistance has required new efforts in drug discovery and development. Thus, the search for new drugs operating by novel mechanisms of action is receiving increased attention. Herein the synthesis and biol. evaluation of a novel anti-malarial with micromolar activity against resistant strains of the parasite is reported. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Reference of 15813-09-9).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) 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.Reference of 15813-09-9

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

β-Lactams with antiproliferative and antiapoptotic activity in breast and chemoresistant colon cancer cells was written by Malebari, Azizah M.;Fayne, Darren;Nathwani, Seema M.;O’Connell, Fiona;Noorani, Sara;Twamley, Brendan;O’Boyle, Niamh M.;O’Sullivan, Jacintha;Zisterer, Daniela M.;Meegan, Mary J.. And the article was included in European Journal of Medicinal Chemistry in 2020.Electric Literature of C8H7IO2 This article mentions the following:

A series of novel 1,4-diaryl-2-azetidinone analogs of combretastatin A-4 (CA-4) have been designed, synthesized and evaluated in vitro for antiproliferative activity, antiapoptotic activity and inhibition of tubulin polymerization Glucuronidation of CA-4 by uridine 5-diphosphoglucuronosyl transferase enzymes (UGTs) has been identified as a mechanism of resistance in cancer cells. Potential sites of ring B glucuronate conjugation are removed by replacing the B ring meta-hydroxy substituent of selected series of β-lactams with alternative substituents e.g., F, Cl, Br, I, and Me. The 3-phenyl-β-lactam I (R¹ = Ph) and 3-hydroxy-β-lactam I (R¹ = OH) (II) demonstrate improved activity over CA-4 in CA-4 resistant HT-29 colon cancer cells (IC₅₀ = 9 nM and 3 nM, resp., compared with IC₅₀ = 4.16μM for CA-4), while retaining potency in MCF-7 breast cancer cells (IC₅₀ = 17 nM and 22 nM, resp., compared with IC₅₀ = for 4 nM for CA-4). Compound II binds at the colchicine site of tubulin, and strongly inhibits tubulin assembly at micromolar concentrations comparable to CA-4. In addition, compound II induced mitotic arrest at low concentration in both cell lines MCF-7 and HT-29 together with down-regulation of expression of antiapoptotic proteins Mcl-1, Bcl-2 and survivin in MCF-7 cells. These novel antiproliferative and antiapoptotic β-lactams are potentially useful scaffolds in the development of tubulin-targeting agents for the treatment of breast cancers and chemoresistant colon cancers. 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. 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.Electric Literature of C8H7IO2

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

Cu-Catalyzed Enantioselective Ring Opening of Cyclic Diaryliodoniums toward the Synthesis of Chiral Diarylmethanes was written by Li, Bin;Chao, Zengyin;Li, Chunyu;Gu, Zhenhua. And the article was included in Journal of the American Chemical Society in 2018.Product Details of 877264-43-2 This article mentions the following:

A Cu-catalyzed enantioselective desymmetrizing ring-opening reaction of six-membered cyclic diaryliodonium salts with carboxylic acids or thioacids is reported for the facile access to chiral diarylmethanes. A Cu/[cyclopropyl bis(oxazoline)] catalyst well discriminates two C-I bonds of prochiral cyclic diaryliodonium salts. A stereochem. model was proposed to rationalize the stereochem. outcome on the basis of the crystal structure of cyclic diaryliodonium salt. In the experiment, the researchers used many compounds, for example, (5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2Product Details of 877264-43-2).

(5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2) 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.Product Details of 877264-43-2

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

Organic iodine compounds in fine particulate matter from a continental urban region: Insights into secondary formation in the atmosphere was written by Shi, Xiaodi;Qiu, Xinghua;Chen, Qi;Chen, Shiyi;Hu, Min;Rudich, Yinon;Zhu, Tong. And the article was included in Environmental Science & Technology in 2021.Related Products of 5460-32-2 This article mentions the following:

Atm. iodine chem. can significantly affect the atm. oxidation capacity in certain regions. In such processes, particle-phase organic iodine compounds (OICs) are key reservoir species in their loss processes. However, their presence and formation mechanism remain unclear, especially in continental regions. Using gas chromatog. and time-of-flight mass spectrometry coupled with both electron capture neg. ionization and electron impact sources, this study systematically identified unknown OICs in 2-yr samples of ambient fine particulate matter (PM_2.5) collected in Beijing, an inland city. We determined the mol. structure of 37 unknown OICs, among which six species were confirmed by reference standards The higher concentrations for ∑₃₇OICs (median: 280 pg m^-3; range: 49.0-770 pg m^-3) measured in the heating season indicate intensive coal combustion sources of atm. iodine. 1-Iodo-2-naphthol and 4-iodoresorcinol are the most abundant species mainly from primary combustion emission and secondary formation, resp. The detection of 2- and 4-iodoresorcinols, but not of iodine-substituted catechol/hydroquinone or 5-iodoresorcinol, suggests that they are formed via the electrophilic substitution of resorcinol by hypoiodous acid, a product of the reaction of iodine with ozone. This study reports isomeric information on OICs in continental urban PM_2.5 and provides valuable evidence on the formation mechanism of OICs in ambient particles. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Related Products of 5460-32-2).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. 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.Related Products of 5460-32-2

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

Leoligin-inspired synthetic lignans with selectivity for cell-type and bioactivity relevant for cardiovascular disease was written by Linder, Thomas;Liu, Rongxia;Atanasov, Atanas G.;Li, Yuanfang;Geyrhofer, Sophie;Schwaiger, Stefan;Stuppner, Hermann;Schnuerch, Michael;Dirsch, Verena M.;Mihovilovic, Marko D.. And the article was included in Chemical Science in 2019.Formula: C8H9IO2 This article mentions the following:

Recently, a natural compound leoligin, a furan-type lignan, was discovered as an interesting hit compound with an anti-inflammatory pharmacol. activity profile. We developed a modular and stereoselective approach for the synthesis of the edelweiss-derived lignan leoligin and used the synthetic route to rapidly prepare leoligin analogs even on the gram scale. Proof of concept of this approach together with cell-based bio-assays gained structural analogs with increased selectivity towards vascular smooth muscle vs. endothelial cell proliferation inhibition, a major benefit in fighting vascular neointima formation. In addition, we identified the structural features of leoligin analogs that define their ability to inhibit the pro-inflammatory NF-κB pathway. Results are discussed in the context of structural modification of these novel synthetic lignans. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Formula: 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.Formula: C8H9IO2

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

Palladium-Catalyzed ortho-Halogenation of Tertiary Benzamides was written by Qiu, Fang-Cheng;Yang, Wen-Cheng;Chang, Yong-Zhen;Guan, Bing-Tao. And the article was included in Asian Journal of Organic Chemistry in 2017.Recommanded Product: N,N-Diethyl-4-iodobenzamide This article mentions the following:

A general and efficient protocol for the synthesis of ortho-halogenated tertiary benzamides under mild conditions was described. Benzamides with various functional groups underwent ortho-iodination, bromination or chlorination with NXS using a cationic palladium catalyst generated in-situ from Pd(OAc)₂ and TfOH in DME. Given the generality, efficiency, mild conditions and readily available catalyst and halogenation reagents, this method provided a practical approach for the synthesis of ortho-halogenated benzamides. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Recommanded Product: N,N-Diethyl-4-iodobenzamide).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) 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. 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.Recommanded Product: N,N-Diethyl-4-iodobenzamide

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

A dual light-driven palladium catalyst: Breaking the barriers in carbonylation reactions was written by Torres, Gerardo M.;Liu, Yi;Arndtsen, Bruce A.. And the article was included in Science (Washington, DC, United States) in 2020.Application In Synthesis of 1-Chloro-4-iodobutane This article mentions the following:

Transition metal-catalyzed coupling reactions have become one of the most important tools in modern synthesis. However, an inherent limitation to these reactions is the need to balance operations, because the factors that favor bond cleavage via oxidative addition ultimately inhibit bond formation via reductive elimination. Here, we describe an alternative strategy that exploits simple visible-light excitation of palladium to drive both oxidative addition and reductive elimination with low barriers. Palladium-catalyzed carbonylations can thereby proceed under ambient conditions, with challenging aryl or alkyl halides and difficult nucleophiles, and generate valuable carbonyl derivatives such as acid chlorides, esters, amides, or ketones in a now-versatile fashion. Mechanistic studies suggest that concurrent excitation of palladium(0) and palladium(II) intermediates is responsible for this activity. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Application In Synthesis of 1-Chloro-4-iodobutane).

1-Chloro-4-iodobutane (cas: 10297-05-9) 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.Application In Synthesis of 1-Chloro-4-iodobutane

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

First total synthesis of fungerin, an antifungal alkaloid from Fusarium sp. was written by Benhida, Rachid;Lezama, Ruth;Fourrey, Jean-Louis. And the article was included in Tetrahedron Letters in 1998.Electric Literature of C3H2I2N2 This article mentions the following:

The first total synthesis of fungerin, a new antifungal alkaloid, is described. Starting from a 4,5-diiodoimidazole derivative, the procedure involves regioselective prenylation and Heck type reaction steps to give fungerin in high yield. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Electric Literature 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. 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 C3H2I2N2

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

Regio- and chemoselective metalation of chloropyrimidine derivatives with TMPMgCl·LiCl and TMP₂Zn·2MgCl₂·2LiCl was written by Mosrin, Marc;Knochel, Paul. And the article was included in Chemistry – A European Journal in 2009.Formula: C4H2ClIN2 This article mentions the following:

Efficient zincation and magnesiation of chlorinated pyrimidines can be performed at convenient temperatures (e.g., 25 and 55°C) by using TMPMgCl·LiCl and TMP₂Zn·2MgCl₂·2LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) as effective bases. Quenching of the resulting zincated or magnesiated pyrimidines with various electrophiles furnishes highly functionalized pyrimidines in 51-93 % yield. Oxidative aminations were carried out, thus leading to aminated pyrimidines. By using this methodol., we have also prepared pharmaceutically relevant pyrazolopyrimidines and the fungicide Mepanipyrim. In the experiment, the researchers used many compounds, for example, 2-Chloro-4-iodopyrimidine (cas: 395082-55-0Formula: C4H2ClIN2).

2-Chloro-4-iodopyrimidine (cas: 395082-55-0) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Formula: C4H2ClIN2

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