Category: iodides-buliding-blocks

Synthesis of eosinophil infiltration inhibitors with antihistaminic activity was written by Gyoten, Michiyo;Nagaya, Hideaki;Fukuda, Shigeru;Ashida, Yasuko;Kawano, Yasuhiko. And the article was included in Chemical & Pharmaceutical Bulletin in 2003.Computed Properties of C4H8ClI This article mentions the following:

A series of [1,2,4]triazolo[1,5-b]pyridazines and imidazo[1,2-b]pyridazines having cyclic amines was synthesized and evaluated for antihistaminic activity and inhibitory effect on eosinophil infiltration. When a piperidine or a piperazine containing a benzhydryl group and a suitable spacer was incorporated at the 6-position, the fused pyridazines were found to exhibit both antihistaminic activity and an inhibitory effect on eosinophil chemotaxis. Above all, one product showed potent antihistaminic activity, but little blockade of central H₁ receptors in contrast with its complete blockade of peripheral H₁ receptors as determined by an ex vivo binding assay. Furthermore, the same product inhibited eosinophil infiltration of the skin caused by a topical antigen challenge in sensitized guinea pigs, while an antihistamine terfenadine was not effective. After the pharmacokinetic study, this product was found to be rapidly hydrolyzed to 2-[6-[[3-[4-(diphenylmethoxy)-piperidino]propyl]amino]imidazo [1,2-b]pyridazin-2-yl]-2-methylpropionic acid dihydrate (TAK-427), which was also orally active. The later product having both antihistaminic and antiinflammatory activity, is currently undergoing clin. trials as a therapeutic agent for atopic dermatitis and allergic rhinitis. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Computed Properties 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. 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.Computed Properties of C4H8ClI

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

Domino Oxidative [Pd]-Catalysis: One-Pot Synthesis of Fluorenones Starting from Simple Benzylamines and Iodo Arenes was written by Ravi Kumar, Devarapalli;Satyanarayana, Gedu. And the article was included in Organic Letters in 2015.Synthetic Route of C8H9IO2 This article mentions the following:

A domino [Pd]-catalysis for the efficient synthesis of fluorenones is presented. The overall reaction proceeds through the formation of a five membered Pd(II)-cycle via a highly regioselective ortho C(sp²)-H activation(s) of simple benzylamine that combines with external iodo arenes to give ortho arylated products. Significantly, the reaction further activates the C(sp³)-H and C(sp²)-H (intramol. oxidative Heck coupling) bonds to give tricyclic imine systems. Then the usual water workup affords the fused tricyclic ketones (fluorenones). Remarkably, this one-pot operation enabled the effective construction of two C-C to three C-C bonds. 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. 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 C8H9IO2

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

Reimer-Tiemann reaction with m-bromo- and m-iodophenol was written by Hodgson, H. H.;Jenkinson, T. A.. And the article was included in Journal of the Chemical Society in 1927.Synthetic Route of C7H5IO2 This article mentions the following:

M-BrC₆H₄OH (67 g.) gives 14 g. of the 4-Br derivative and 15 g. of the isomeric 2,4-Br(HO)C₆H₃CHO. 4-Bromo-2-hydroxybenzaldehyde p-nitrophenylhydrazone, orange-yellow, m. 258° (decomposition); semicarbazone, m. 212°; benzoate, m. 115°. 4-Bromo-2-methoxybenzaldehyde, m. 71°; oxime, m. 132°; p-nitrophenylhydrazone, bright orange, m. 215°; semicarbazone, m. 224°; 4-bromo-2-methoxybenzoic acid, m. 155°. 4-Bromo-2-hydroxybenzoic acid, m. 214°; FeCl₃ gives a violet color. 2-Bromo-4-hydroxybenzaldehyde p-nitrophenylhydrazone, dark red, m. 274° (decomposition); semicarbazone, m. 212°; oxime, m. 184°; 2-bromo-4-hydroxybenzoic acid, m. 151°; FeCl₃ gives faint pink color. 2-Bromo-4-methoxybenzaldehyde, m. 77°; oxime, m. 93°; p-nitrophenylhydrazone, orange-red, m. 250°; semicarbazone, m. 232°; 2-bromo-4-methoxybenzoic acid, m. 199°. 2,4-Cl(MeO)C₆H₃CHO, m. 62.5°, yields an oxime, m. 93°; a p-nitrophenylhydrazone, orange-red, m. 249° (decomposition); and a semicarbazone, m. 240°. m-IC₆H₄OH (73 g.) gives 12 g. of 4-iodo-2-hydroxybenzaldehyde (I), m. 87°, and 2-iodo-hydroxybenzaldehyde (II), very pale yellow, m. 163°. The alkali metal, NH₄ and Ag salts of I are all yellow; the Cu salt is green; oxime, m. 171°; p-nitrophenylhydrazone, orange, m. 242° (decomposition); semicarbazone, pale yellow, m. 252°; benzoate, m. 62°. 4-Iodo-2-hydroxybenzoic acid, m. 230°; FeCl₃ gives a reddish violet color. 4-Iodo-2-methoxybenzaldehyde, m. 85°; oxime, m. 138°; p-nitrophenylhydrazone, orange-red, m. 238° (decomposition); semicarbazone, m. 228°; 4-iodo-2-methoxybenzoic acid, m. 150°, sublimes 120-30° and evolves I above its m. p. The alkali metal derivatives of II are yellow and the Cu derivative is less bluish green than that of I; p-nitrophenylhydrazone, dark red, m. 265° (decomposition); semicarbazone, pale yellow, m. 232° (decomposition); oxime, m. 155°; benzoate, m. 112°; 2-iodo-4-hydroxybenzoic acid, m. 179° (decomposition); gives no color with FeCl₃. 2-Iodo-4-methoxybenzaldehyde, m. 115°; p-nitrophenylhydrazone, reddish orange, m. 246° (decomposition); semicarbazone, pale yellow, m. 211°; oxime, m. 101°; 2-iodo-4-methoxybenzoic acid, m. 184°. In the experiment, the researchers used many compounds, for example, 4-Hydroxy-2-iodobenzaldehyde (cas: 90151-01-2Synthetic Route of C7H5IO2).

4-Hydroxy-2-iodobenzaldehyde (cas: 90151-01-2) 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. 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 C7H5IO2

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

Three chloro(trifluoromethyl)pyridines as model substrates for regioexhaustive functionalization was written by Cottet, Fabrice;Schlosser, Manfred. And the article was included in European Journal of Organic Chemistry in 2004.Name: 2-Chloro-5-(trifluoromethyl)-4-iodopyridine This article mentions the following:

As a further test of the concept of regioexhaustive functionalization, 2-chloro-6-(trifluoromethyl)pyridine, 2-chloro-5-(trifluoromethyl)pyridine and 3-chloro-4-(trifluoromethyl)pyridine were each converted into the three possible carboxylic acids. This was achieved by employing several, but not all of the organometallic “toolbox methods”; transformation of a more basic organometallic species into a less basic isomer by transmetalation-equilibration, site discriminating deprotonation with lithium N,N-diisopropylamide or lithium 2,2,6,6-tetramethylpiperidide, regio-divergent iodine migration and steric screening of acidic positions by a bulky trialkylsilyl group. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-(trifluoromethyl)-4-iodopyridine (cas: 505084-55-9Name: 2-Chloro-5-(trifluoromethyl)-4-iodopyridine).

2-Chloro-5-(trifluoromethyl)-4-iodopyridine (cas: 505084-55-9) 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. 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.Name: 2-Chloro-5-(trifluoromethyl)-4-iodopyridine

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

Synthesis and biological evaluation of novel flexible nucleoside analogues that inhibit flavivirus replication in vitro was written by Thames, Joy E.;Waters, Charles D. III;Valle, Coralie;Bassetto, Marcella;Aouadi, Wahiba;Martin, Baptiste;Selisko, Barbara;Falat, Arissa;Coutard, Bruno;Brancale, Andrea;Canard, Bruno;Decroly, Etienne;Seley-Radtke, Katherine L.. And the article was included in Bioorganic & Medicinal Chemistry in 2020.Safety of 4,5-Diiodo-1H-imidazole This article mentions the following:

Flaviviruses, such as Dengue (DENV) and Zika (ZIKV) viruses, represent a severe health burden. There are currently no FDA-approved treatments, and vaccines against most flaviviruses are still lacking. We have developed several flexible analogs (“fleximers”) of the FDA-approved nucleoside Acyclovir that exhibit activity against various RNA viruses, demonstrating their broad-spectrum potential. The current study reports activity against DENV and Yellow Fever Virus (YFV), particularly for compound 1. Studies to elucidate the mechanism of action suggest the flex-analog triphosphates, especially 1-TP, inhibit DENV and ZIKV methyltransferases, and a secondary, albeit weak, effect on the DENV RNA-dependent RNA polymerase was observed at high concentrations The results of these studies are reported herein. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Safety of 4,5-Diiodo-1H-imidazole).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. 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.Safety of 4,5-Diiodo-1H-imidazole

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

Palladium-Catalyzed Direct Oxidative Coupling of Iodoarenes with Primary Alcohols Leading to Ketones: Application to the Synthesis of Benzofuranones and Indenones was written by Suchand, Basuli;Sreenivasulu, Chinnabattigalla;Satyanarayana, Gedu. And the article was included in European Journal of Organic Chemistry in 2019.Reference of 5460-32-2 This article mentions the following:

In the present study, a palladium-catalyzed direct oxidative acylation through cross-dehydrogenative coupling has been investigated, utilizing readily available primary alcs. as acylating sources. Overall, this oxidative coupling proceeds via three distinct transformations such as oxidation, radical formation, and cross-coupling in one catalytic process. This protocol does not involve the assistance of a directing group or activation of the carbonyl group by any other means. Furthermore, this reaction made use of no toxic CO gas as carbonylating agent; instead, feedstock primary alcs. have been utilized as acylation source. Notably, the synthesis of benzofuranones and indenones is enabled. This strategy was also applied to the synthesis of n-butylphthalide, fenofibrate, pitofenone, and neo-lignan. Thus, e.g., Me 2-iodobenzoate + benzyl alc. → Me 2-benzoylbenzoate (64%) in presence of Pd(OAc)₂, Ag₂O and TBHP. 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. 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.Reference of 5460-32-2

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

Modulation of π-electron conjugation in oligo(triacetylene) chromophores by incorporation of a central spacer was written by Martin, Rainer E.;Wytko, Jennifer A.;Diederich, Francois;Boudon, Corinne;Gisselbrecht, Jean-Paul;Gross, Maurice. And the article was included in Helvetica Chimica Acta in 1999.Synthetic Route of C10H12I2 This article mentions the following:

A series of trimeric hybrid oligomers was prepared by insertion of different hetero-spacers between two (E)-hex-3-ene-1,5-diyne (E = 1,2-diethynylethene, DEE) moieties, and the optical and electrochem. properties of the resulting π-conjugated materials were compared to those of the DEE dimer and trimer, which formally contain a DEE moiety as homo-spacer. The hetero-spacers were: benzenoid (phenylene, naphthalene, biphenylene, anthracene), π-electron-deficient (pyrazine, pyridine) and π-electron-rich (thiophene, furan) aromatic rings, and trans-Pt(PEt₃)₂. The hybrid oligomers were synthesized using the method of K. Sonogashira et al. (1978), i.e., cross-coupling between mono-deprotected DEE and the appropriately bis-functionalized spacer. UV/VIS data revealed that the majority of the hetero-spacers were less effective than the homo-spacer DEE in facilitating π-electron delocalization along the linearly conjugated oligomeric backbone. With increasing degree of benzenoid aromaticity in the hetero-spacer, the electronic communication between the terminal DEE moieties in the hybrid oligomers was reduced. As a remarkable exception, a large bathochromic shift of the longest-wavelength absorption maximum, which is indicative of enhanced π-electron delocalization, was obtained upon introducing an anthracene-9,10-diyl moiety as hetero-spacer. Electrochem. studies by cyclic and steady-state voltammetry confirmed the limited extent of π-electron delocalization in the majority of the hybrid oligomers. The fluorescence properties of many of the DEE hybrid materials were dramatically enhanced upon incorporation of the heterospacers. The heterocyclic derivatives containing pyridine, pyrazine, or thiophene spacers, resp., displayed a strong fluorescence emission, demonstrating the value of combining repeat units to modulate oligomeric and polymeric properties. The pyridine derivative provided an interesting example of a mol. system, in which both the electronic absorption and emission characteristics can be reversibly switched as a function of pH. In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1Synthetic Route of C10H12I2).

1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Synthetic Route of C10H12I2

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

Cobalt-catalysed enantioselective C(sp³)-C(sp³) coupling was written by Li, Yan;Nie, Wan;Chang, Zhe;Wang, Jia-Wang;Lu, Xi;Fu, Yao. And the article was included in Nature Catalysis in 2021.Recommanded Product: 10297-05-9 This article mentions the following:

Enantioselective C(sp³)-C(sp³) coupling substantially impacts organic synthesis but remains challenging. Cobalt has played an important role in the development of homogeneous organometallic catalysis, but there are few examples of its use in asym. cross-coupling. Here, a cobalt-catalyzed enantioselective C(sp³)-C(sp³) coupling reaction, namely, alkene hydroalkylation, to access chiral fluoroalkanes was reported. This reaction represents a catalyst-controlled enantioselective coupling mode in which a tailor-made auxiliary is unnecessary; via this reaction, an aliphatic C-F stereogenic center can be introduced at the desired position in an alkyl chain. 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. 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.Recommanded Product: 10297-05-9

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

Palladium-catalyzed asymmetric coupling cyclization of terminal γ-allenols with aryl iodides was written by Xie, Xi;Ma, Shengming. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2013.Quality Control of N,N-Diethyl-4-iodobenzamide This article mentions the following:

A Pd-catalyzed asym. coupling cyclization of γ-allenols with aryl iodides has been developed. α-(Tetrahydrofuran-2-yl)styrene derivatives can be prepared in 60-86% yields with ee values ranging from 85-92%. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Quality Control of 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.Quality Control of N,N-Diethyl-4-iodobenzamide

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

Proton Transfer Can Govern Regioselectivity Assisted by Iron Catalysis was written by Li, Yudong;Fu, Liyan;Jiang, Xiaolin;Zhao, Dongmei;Wang, Hui-Fang;Xia, Chungu;Li, Yuehui. And the article was included in iScience in 2020.Application of 207115-22-8 This article mentions the following:

Ortho-selective aromatic C-H functionalization is frequently used in organic synthesis and chem./pharmaceutical industries. However, this reaction relies heavily on the use of directing groups suffering from limited substrate scope and extra steps to put on and remove the directing/protecting groups. Herein authors present the previously neglected concept that enables good to nearly complete selective ortho position. Proton transfer was utilized to tune the electron d. on the aryl ring and determine the positional selectivity of electrophilic substitution. Consistently with deuteration experiments and DFT studies, this work demonstrates that acid-promoted proton transfer directs accelerated ortho-selective halogenation of NH/OH contained aromatic amines/phenols with excellent selectivity (>40 examples; up to 98:2 ortho/para selectivity). The application potential of this Fe-catalyzed method is demonstrated by the convenient synthesis of three alkaloids and tizanidine. This report raises the possibility that proton transfer could serve as the basis of developing new selective C-H functionalization reactions. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Application of 207115-22-8).

4-Bromo-2-iodophenol (cas: 207115-22-8) 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.Application of 207115-22-8

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