Category: iodides-buliding-blocks

In 2019,Chemistry – A European Journal included an article by Schmitz, Alexander J.; Ricke, Alexander; Oschmann, Michael; Verho, Oscar. Safety of 1-Bromo-4-iodobenzene. The article was titled 《Convenient Access to Chiral Cyclobutanes with Three Contiguous Stereocenters from Verbenone by Directed C(sp3)-H arylation》. The information in the text is summarized as follows:

This work demonstrates how a series of complex, chiral cyclobutane derivatives can be accessed in four steps from the terpene verbenone through the application of a directed C-H functionalization approach. The developed synthetic route involved an 8-aminoquinoline-directed C(sp3)-H arylation as the key step, and this reaction could be carried out with a wide range of aryl and heteroaryl iodides to furnish a variety of cyclobutane products I (Ar = Ph, 4-ClC6H4, 2-thienyl, etc.; Q = quinolin-8-yl) with three contiguous stereocenters. Moreover, it was shown that the 8-aminoquinoline auxiliary could be effectively removed from the cyclobutane derivatives using an ozonolysis-based cleavage method. In addition to this study using 1-Bromo-4-iodobenzene, there are many other studies that have used 1-Bromo-4-iodobenzene(cas: 589-87-7Safety of 1-Bromo-4-iodobenzene) was used in this study.

1-Bromo-4-iodobenzene(cas: 589-87-7) has been employed as reagent for in situ desilylation and coupling of silylated alkynes, as starting reagent in the total syntheses of ent-conduramine A and ent-7-deoxypancratistatin (alkaloids), as substrate in copper-free Sonogashira coupling in aqueous acetone in synthesis of β,β,dibromostyrenesSafety of 1-Bromo-4-iodobenzene

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

In 2019,Beilstein Journal of Nanotechnology included an article by Jana, Achintya; Mishra, Puneet; Das, Neeladri. SDS of cas: 15854-87-2. The article was titled 《Polymorphic self-assembly of pyrazine-based tectons at the solution-solid interface》. The information in the text is summarized as follows:

The synthesis and surface self-assembly of a new pyrazine-derived mol. with pyridine pendants I was reported. Ambient scanning tunneling microscopy investigation at the solution-solid interface revealed polymorphic self-assembly of these mols. on a HOPG substrate. Two different mol. packing structures with equal distribution were observed Detailed anal. of the STM images emphasized the crucial role of weak intermol. hydrogen bonding, and mol.-substrate interactions in the formation of the observed polymorphs. Such weak hydrogen bonding interactions were highly desirable for the formation of modular supramol. architectures since they could provide sufficiently robust mol. structures and also facilitate error correction. The experimental process involved the reaction of 4-Iodopyridine(cas: 15854-87-2SDS of cas: 15854-87-2)

4-Iodopyridine(cas: 15854-87-2) belongs to pyridine. Pyridine’s structure is isoelectronic with that of benzene, but its properties are quite different. Pyridine is completely miscible with water, whereas benzene is only slightly soluble. Like all hydrocarbons, benzene is neutral (in the acid–base sense), but because of its nitrogen atom, pyridine is a weak base.SDS of cas: 15854-87-2

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

In 2019,Angewandte Chemie, International Edition included an article by Lee, Yong Ho; Morandi, Bill. SDS of cas: 90-14-2. The article was titled 《Palladium-Catalyzed Intermolecular Aryliodination of Internal Alkynes》. The information in the text is summarized as follows:

A completely atom economical palladium-catalyzed addition reaction has been developed to stereoselectively access functionalized tetrasubstituted alkenyl iodides. The palladium catalyst, which bears an electron-poor bidentate ligand rarely employed in catalysis, is essential to promote the high yielding and chemoselective intermol. reaction between equimolar amounts of an alkyne and an aryl iodide. This new carbohalogenation reaction is an attractive alternative to traditional synthetic methods, which rely on multistep synthetic sequences and protecting-group manipulations. After reading the article, we found that the author used 1-Iodonaphthalene(cas: 90-14-2SDS of cas: 90-14-2)

1-Iodonaphthalene(cas: 90-14-2) is one of organic iodides. Organic iodides are used in veterinary products (Organic Iodide Powder) as a nutritional source 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. Oceanic alkyl iodides are believed to be the principal source of atmospheric iodine.SDS of cas: 90-14-2

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

In 2016,McNeece, Andrew J.; Mokhtarzadeh, Charles C.; Moore, Curtis E.; Rheingold, Arnold L.; Figueroa, Joshua S. published 《Nickel bis-m-terphenylisocyanide dihalide complexes formed from 1,2-alkyl dihalides: probing for isolable β-haloalkyl complexes of square planar nickel》.Journal of Coordination Chemistry published the findings.Name: 1,2-Diiodoethane The information in the text is summarized as follows:

The pentachloroethyl complex NiCl(CCl2CCl3)(CNArMes2)2 (ArMes2 = 2,6-(2,4,6-Me3C6H2)2C6H3) was recently shown to be a unique example of an isolable β-chloroalkyl complex of square planar Ni. In an effort to generate addnl. β-haloalkyl complexes of square planar nickel, the reactivity of the precursor complex Ni(COD)(CNArMes2)2 with alkyl halides was probed. Treatment of Ni(COD)(CNArMes2)2 with 1,2-dichloroethane results in the exclusive formation of the dichloride complex NiCl2(CNArMes2)2 without the buildup of detectable intermediates. Similarly, Ni(COD)(CNArMes2)2 reacts with either 1,2-dibromoethane or 1,2-diiodoethane to produce the dibromide, NiBr2(CNArMes2)2, and diiodide, NiI2(CNArMes2)2, species, resp. Observable intermediates were also not detected in these latter reactions, indicating that either β-halo elimination is rapid or 1e- halogen-atom abstraction pathways are accessible to Ni(COD)(CNArMes2)2. The sterically and electronically modified m-terphenyl isocyanides CNArDipp2 and CNArClips2 (ArDipp2 = 2,6-(2,6-(i-Pr)2C6H3)2C6H3; ArClips2 = 2,6-(2,6-(Cl)2C6H3)2-4-(t-Bu)C6H2) were also studied as ancillary ligands for stabilization of a β-chloroalkyl complex of square planar nickel. Treatment of the zero-valent precursors Ni(COD)(CNArDipp2)2 and Ni(COD)(CNArClips2)2 with either 1,2-dichloroethane or hexachloroethane resulted in rapid formation of the dichlorides NiCl2(CNArDipp2)2 and NiCl2(CNArClips2)2 as exclusive products. These results highlight the unique combination of steric and electronic properties that lead to the stability of the parent β-chloroalkyl complex NiCl(CCl2CCl3)(CNArMes2)2. In addition to this study using 1,2-Diiodoethane, there are many other studies that have used 1,2-Diiodoethane(cas: 624-73-7Name: 1,2-Diiodoethane) was used in this study.

1,2-Diiodoethane(cas: 624-73-7) is one of organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles.Name: 1,2-Diiodoethane

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

Reference of 2-Chloro-5-iodo-3-(trifluoromethyl)pyridineOn June 5, 2020, Reddy, Chennakesava; Shaikh, Javed Y.; Bhat, Ramakrishna G. published an article in Journal of Organic Chemistry. The article was 《Access to Hetero-Benzyl Scaffolds via Transient-Ligand-Enabled Direct γ-C(sp3)-H Arylation of 3-Methylheteroarene-2-Carbaldehydes》. The article mentions the following:

An efficient and straightforward method has been developed for the synthesis of β-benzyl-substituted 5-membered heterocyclic carbaldehydes via transient directing-group-enabled direct γ-C(sp3)-H arylation of 3-methylheteroarene-2-carbaldehydes. A wide range of 3-methylheteroarene carbaldehydes undergo coupling with a variety of aryl iodides, including less reactive iodo pyridine derivatives to provide a library of highly selective functionalized products in good to excellent yields. Some of these products have been successfully utilized in synthesizing useful synthetic intermediates. In the experiment, the researchers used 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7Reference of 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine)

2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Reference of 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine

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

Safety of 4-Chloro-5-iodo-2,6-dimethylpyrimidineOn October 22, 1998 ,《Metabolites of the Angiotensin II Antagonist Tasosartan: The Importance of a Second Acidic Group》 was published in Journal of Medicinal Chemistry. The article was written by Ellingboe, John W.; Collini, Michael D.; Quagliato, Dominick; Chen, James; Antane, Madelene; Schmid, Jean; Hartupee, Dale; White, Valerie; Park, C. Hyung; Tanikella, Tarak; Bagli, Jehan F.. The article contains the following contents:

Described in this paper is the synthesis and pharmacol. activity of five metabolites of the angiotensin II antagonist tasosartan (1). Of particular interest is the effect of the addnl. acidic group of the enol metabolite (8) on activity. As suggested by the structural-activity relationship of other angiotensin II antagonist series, a second acidic group can improve receptor binding activity but decrease in vivo activity after oral dosing. The metabolic introduction of a second acidic group in tasosartan bypasses this problem and contributes to the excellent profile of the compound A mol. modeling study provides a rationale for the role of the enol group of 8 in AT1 receptor binding. The experimental process involved the reaction of 4-Chloro-5-iodo-2,6-dimethylpyrimidine(cas: 83410-16-6Safety of 4-Chloro-5-iodo-2,6-dimethylpyrimidine)

4-Chloro-5-iodo-2,6-dimethylpyrimidine(cas: 83410-16-6) is one of organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles.Safety of 4-Chloro-5-iodo-2,6-dimethylpyrimidine

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

Application In Synthesis of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthaleneOn September 30, 2001 ,《Chiral conjugated oligomer based on 1,1′-binol with 3,3′-acetylene-phenylene-acetylene spacer》 was published in Chinese Journal of Polymer Science. The article was written by Liu, Tian-Jun; Zhang, Ke-Shen; Chen, Yong-Jun; Wang, Dong; Li, Chao-Jun. The article contains the following contents:

The 1,1′-binaphthol based oligomers 3 and 7 with 3,3′-acetylene-phenylene-acetylene spacer were prepared from BINOL 1. The high optical rotation value and CD spectra demonstrated the main chain chirality of the oligomer mol. The UV-VIS and fluorescent spectra evidence the characteristics of conjugated structure. In comparison with oligomer 2 bearing 3,3′-acetylene spacer, the oligomers 3 and 7 have longer efficient conjugation segment, and their fluorescent quantum yields (φ) increased (0.60-0.65 vs. 0.14). Extending the effective conjugation segment would improve the photophys. properties of chiral conjugated polymers. The results came from multiple reactions, including the reaction of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3Application In Synthesis of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene)

(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3) belongs to organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Application In Synthesis of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene

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

《Palladium(II)-Catalyzed Sp3/Sp2 γ- and δ-C-H Functionalization of Aryl Amines using 5-Methylisoxazole-3-Carboxamide as Directing Group》 was written by Singh, Prabhakar; Dalal, Arup; Babu, Srinivasarao Arulananda. Electric Literature of C7H7IThis research focused ontoluidine iodoarene palladium catalyst methylisoxazole carboxamide directed regioselective arylation; benzylamine iodoarene palladium catalyst methylisoxazole carboxamide directed regioselective arylation; diacetoxyiodo benzene toluidine palladium methylisoxazole carboxamide directed regioselective acetoxylation; iodosobenzene diacetate benzylamine palladium methylisoxazole carboxamide directed regioselective acetoxylation; phenethylamine palladium catalyst methylisoxazole carboxamide directed regioselective amidation heterocyclization; aminoethyl benzene palladium catalyst methylisoxazole carboxamide directed regioselective alkenylation. The article conveys some information:

The study comprising exploration of 5-methylisoxazole-3-carboxamide as a directing group (DG) for the Pd(II)-catalyzed sp3/sp2 γ- and δ-C-H activation/functionalization of aryl amines and assembling of various MICA motifs were reported. The Pd(II)-catalyzed MICA-aided γ-C(sp3)-H arylation/acetoxylation of ortho-toluidines gave various 2-aminodiphenylmethanes and 2-aminobenzyl acetates resp. The Pd(II)-catalyzed MICA-aided γ-C(sp2)-H arylation/acetoxylation of benzylamines gave the corresponding arylated/acetoxylated products. Furthermore, the Pd(II)-catalyzed MICA-aided δ-C(sp2)-H amidation/alkenylation of phenethylamines were also explored. Representative control reactions were done to assessed the relative effectiveness of MICA for the γ-C(sp3)-H arylation and MICA was a removable DG. Apart from the usage of MICA as a DG for the sp2/sp3 C-H functionalization of aryl amines, indirectly this process was led to the construction of a library of MICA motifs. This is an added advantage to note as the MICA-based motifs were valuable small mols. in medicinal chem. The experimental part of the paper was very detailed, including the reaction process of 1-Iodo-4-methylbenzene(cas: 624-31-7Electric Literature of C7H7I)

1-Iodo-4-methylbenzene(cas: 624-31-7) is used in wide range of medicals industrial applications as well as in pharmaceutical intermediates, polarizing films for Liquid Crystal Display (LCD) chemicals.Electric Literature of C7H7I

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

《New V1a receptor antagonist. Part 2. Identification and optimization of triazolobenzazepines》 was written by Bozo, Eva; Baska, Ferenc; Lovei, Klara; Szanto, Gabor; Domany-Kovacs, Katalin; Kurko, Dalma; Szondine Kordas, Krisztina; Szokoli, Teodora; Bata, Imre. Safety of Trimethylsulfoxonium iodideThis research focused onvasopressin V1a antagonist HTS synthesis triazolobenzazepines; Antagonist; HTS; Synthesis; Triazolobenzazepines; V1a; Vasopressin. The article conveys some information:

Solid preclin. evidence links vasopressin to social behavior in animals, so, extensive work has been initiated to find new vasopressin V1a receptor antagonists which can improve deteriorated social behavior in humans and can treat the core symptoms of autistic behavior, as well. Our aim was to identify new chem. entities with antagonizing effects on vasopressin V1a receptors. Continuing our previous work, we found an in vitro and in vivo orally active V1a selective antagonist mol. (40) among [1,2,4]triazolo[4,3-a][1]benzazepines. In the experimental materials used by the author, we found Trimethylsulfoxonium iodide(cas: 1774-47-6Safety of Trimethylsulfoxonium iodide)

Trimethylsulfoxonium iodide(cas: 1774-47-6) reacts with sodium hydride to prepare dimethyloxosulfonium methylide, which is used as a methylene-transfer reagent in synthetic chemistry. It is used to prepare ylide, which reacts with carbonyl compounds to get epoxides.Safety of Trimethylsulfoxonium iodide

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

Application of 301673-14-3In 2022 ,《A Small-Molecule Oral Agonist of the Human Glucagon-like Peptide-1 Receptor》 was published in Journal of Medicinal Chemistry. The article was written by Griffith, David A.; Edmonds, David J.; Fortin, Jean-Philippe; Kalgutkar, Amit S.; Kuzmiski, J. Brent; Loria, Paula M.; Saxena, Aditi R.; Bagley, Scott W.; Buckeridge, Clare; Curto, John M.; Derksen, David R.; Dias, Joao M.; Griffor, Matthew C.; Han, Seungil; Jackson, V. Margaret; Landis, Margaret S.; Lettiere, Daniel; Limberakis, Chris; Liu, Yuhang; Mathiowetz, Alan M.; Patel, Jayesh C.; Piotrowski, David W.; Price, David A.; Ruggeri, Roger B.; Tess, David A.. The article contains the following contents:

Peptide agonists of the glucagon-like peptide-1 receptor (GLP-1R) have revolutionized diabetes therapy, but their use has been limited because they require injection. Herein, we describe the discovery of the orally bioavailable, small-mol., GLP-1R agonist PF-06882961 (danuglipron). A sensitized high-throughput screen was used to identify 5-fluoropyrimidine-based GLP-1R agonists that were optimized to promote endogenous GLP-1R signaling with nanomolar potency. Incorporation of a carboxylic acid moiety provided considerable GLP-1R potency gains with improved off-target pharmacol. and reduced metabolic clearance, ultimately resulting in the identification of danuglipron. Danuglipron increased insulin levels in primates but not rodents, which was explained by receptor mutagenesis studies and a cryogenic electron microscope structure that revealed a binding pocket requiring a primate-specific tryptophan 33 residue. Oral administration of danuglipron to healthy humans produced dose-proportional increases in systemic exposure (NCT03309241). This opens an opportunity for oral small-mol. therapies that target the well-validated GLP-1R for metabolic health. In the part of experimental materials, we found many familiar compounds, such as tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Application of 301673-14-3)

tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3) is one of organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles.Application of 301673-14-3

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