Month: October 2022

In 2022,Le Vaillant, Franck; Mateos Calbet, Ana; Gonzalez-Pelayo, Silvia; Reijerse, Edward J.; Ni, Shengyang; Busch, Julia; Cornella, Josep published an article in Nature (London, United Kingdom). The title of the article was 《Catalytic synthesis of phenols with nitrous oxide》.Reference of 1-Bromo-3-iodobenzene The author mentioned the following in the article:

Here, an insertion of N2O into a Ni-C bond under mild conditions (room temperature, 1.5-2 bar N2O) for delivering valuable phenols ROH (R = Ph, 4-cyanophenyl, 1-oxo-2,3-dihydro-1H-inden-4-yl, quinolin-6-yl, etc.) and releasing benign N2 was reported. This fundamentally distinct organometallic C-O bond-forming step differs from the current strategies based on reductive elimination and enables an alternative catalytic approach for the conversion of aryl halides RX (X = I, Br) to phenols. The process was rendered catalytic by means of a bipyridine-based ligands for the Ni center. The method is robust, mild and highly selective, and able to accommodate base-sensitive functionalities as well as permitting phenol synthesis from densely functionalized aryl halides. Although this protocol does not provide a solution to the mitigation of N2O emissions, it represents a reactivity blueprint for the mild revalorization of abundant N2O as an O source. In the part of experimental materials, we found many familiar compounds, such as 1-Bromo-3-iodobenzene(cas: 591-18-4Reference of 1-Bromo-3-iodobenzene)

1-Bromo-3-iodobenzene(cas: 591-18-4) has been used in the preparation of 1-(3′-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-ene and 1-(3′-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene.Reference of 1-Bromo-3-iodobenzene

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

Reference of 4-Iodobenzoic acidIn 2020 ,《Radioiodinated Nitroxide Derivative for the Detection of Lipid Radicals》 appeared in ACS Medicinal Chemistry Letters. The author of the article were Yamasaki, Toshihide; Azuma, Risa; Sano, Kohei; Munekane, Masayuki; Matsuoka, Yuta; Yamada, Ken-ichi; Mukai, Takahiro. The article conveys some information:

Thus far, no accurate measurement technol. has been developed to detect lipid alkyl radicals (lipid radicals), which cause lipid peroxidation Therefore, we aimed to develop a nuclear medical imaging probe that can be taken up in the lipophilic site in cells such as biol. membranes, by reacting specifically with the lipid radicals generated there. We designed and synthesized 4-(4-[125I]iodobenzamido)-2,2,6,6-tetramethylpiperidine-1-oxyl (I), which shows high reactivity to lipid radicals with a high radiochem. yield and purity. Intracellular retention was found to increase significantly when lipid radicals were produced. In the experiment, the researchers used 4-Iodobenzoic acid(cas: 619-58-9Reference of 4-Iodobenzoic acid)

4-Iodobenzoic acid(cas: 619-58-9) belongs to 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.Reference of 4-Iodobenzoic acid

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

Reference of 1,2-DiiodoethaneIn 2015 ,《SmI2-mediated dimerization of indolylbutenones and synthesis of the myxobacterial natural product indiacen B》 was published in Beilstein Journal of Organic Chemistry. The article was written by Marsch, Nils; Jones, Peter G.; Lindel, Thomas. The article contains the following contents:

The synthesis and reactivity of indole derivatives substituted in the benzene section was studied. Starting materials 4- and 6-iodoindole were conveniently prepared via the Batcho-Leimgruber route and purified by sublimation. Novel vicinally indolyl-substituted cyclopentanols with unexpected cis-configuration were formed by SmI2-mediated reductive dimerization of a 4-(indol-6-yl)butenone, obtained by Heck reaction (I → II with R1 = OH, R2 = Me and vice versa). The two indolyl units appear to chelate Sm(II)/(III) leading to a gauche-type arrangement at the newly formed bond between the two β-carbons. Through a sequence of Sonogashira cross coupling and Meyer-Schuster rearrangement 6-prenoylindole was synthesized and reductively dimerized to a cyclopentane in a [3 + 2] cycloaddition by treatment with SmI2 in THF. From 4-iodoindole, the natural product indiacen B (III) from the myxobacterium Sandaracinus amylolyticus was synthesized for the first time, confirming its antimicrobial activity. The E-configuration of the chloroalkene moiety of indiacen B was confirmed by X-ray anal. In addition to this study using 1,2-Diiodoethane, there are many other studies that have used 1,2-Diiodoethane(cas: 624-73-7Reference of 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.Reference of 1,2-Diiodoethane

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

SDS of cas: 63069-48-7In 2021 ,《Iodine-Catalyzed Methylthiolative Annulation of 2-Alkynyl Biaryls with DMSO: A Metal-Free Approach to 9-Sulfenylphenanthrenes》 was published in Journal of Organic Chemistry. The article was written by Mukherjee, Nilanjana; Chatterjee, Tanmay. The article contains the following contents:

An iodine-catalyzed sustainable, cost-effective, and atom-economic synthetic methodol. is developed to synthesize a wide variety of valuable sulfenylphenanthrenes I (R = Me, CD3, Ph; R1 = C6H5, 4-CN-C6H4, 3-CH3-C6H4, etc.; R2 = H, 6-Cl; R3 = H, 2-Cl, 2-Br, 2-F, etc.) and polycyclic heteroaromatics e.g., II in moderate to high yield through electrophilic thiolative annulation of 2-alkynyl biaryls such as., 3-(2-(Phenylethynyl)phenyl)thiophene (6-endo-dig cyclization) using Me sulfoxides such as DMSO (DMSO) as the sulfur source under transition-metal-free conditions. The transformation requires only iodine in a catalytic amount and trifluoroacetic anhydride. Notably, DMSO played multiple roles such as methylthiolating reagent, oxidant, and solvent in this reaction. The experimental process involved the reaction of 4-Chloro-2-iodoaniline(cas: 63069-48-7SDS of cas: 63069-48-7)

4-Chloro-2-iodoaniline(cas: 63069-48-7) belongs to anime. Examples of direct uses of amines and their salts are as corrosion inhibitors in boilers and in lubricating oils (morpholine), as antioxidants for rubber and roofing asphalt (diarylamines), as stabilizers for cellulose nitrate explosives (diphenylamine), as protectants against damage from gamma radiation (diarylamines), as developers in photography (aromatic diamines), as flotation agents in mining, as anticling and waterproofing agents for textiles, as fabric softeners, in paper coating, and for solubilizing herbicides.SDS of cas: 63069-48-7

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

《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

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

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

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

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