Tag: 200-300

《Influence of Substituents in the Aromatic Ring on the Strength of Halogen Bonding in Iodobenzene Derivatives》 was written by Chernysheva, Maria V.; Bulatova, Margarita; Ding, Xin; Haukka, Matti. Name: 3-Iodophenol And the article was included in Crystal Growth & Design in 2020. The article conveys some information:

The halogen-bonding properties of 3,4,5-triiodobenzoic acid (1, 2), 1,2,3-triiodobenzene (3), 4-iodobenzoic acid (4), pentaiodobenzoic acid ethanol solvate (5), hexaiodobenzene (6a-c), 4-iodobenzonitrile (7), 3-iodobenzonitrile (8), 2,4-diiodoaniline (9), 4-iodoaniline (10), 2-iodoaniline (11), 2-iodophenol (12), 4-iodophenol (13), 3-iodophenol (14), 2,4,6-triiodophenol (15), 4-iodoanisole (16), and 3,4,5-triiodoanisole (17) have been studied. The results suggested that substituents other than halogen in the aromatic ring affect the XB properties of iodide substituents in ortho, meta, and para positions. The effect depends on the electron-withdrawing/electron-donating properties of the substituent. Thus, electron-donating substituents with a pos. mesomeric effect favor m-iodines to act as XB donors. In contrast, electron substituents with a neg. mesomeric effect favor o- and p-iodines to act as XB donors. Furthermore, the stronger the mesomeric effect of the EWG or EDG substituent, the higher the effect it has on the size of the σ-hole and, consequently, on the XB donor ability of the iodide substituent. Structural and computational MEP analyses of 3,4,5-triiodobenzoic acid (1, 2), 1,2,3-triiodobenzene (3), 4-iodobenzoic acid (4), pentaiodobenzoic acid ethanol solvate (5), hexaiodobenzene (6a-c), 4-iodobenzonitrile (7), 3-iodobenzonitrile (8), 2,4-diiodoaniline (9), 4-iodoaniline (10), 2-iodoaniline (11), 2-iodophenol (12), 4-iodophenol (13), 3-iodophenol (14), 2,4,6-triiodophenol (15), 4-iodoanisole (16), and 3,4,5-triiodoanisole (17) have been conducted. The results show that the mesomeric effect of the substituents other than halogen in the benzene ring has an effect on the XB donor-acceptor properties of the iodide substituents in ortho, meta, and para positions. Thus, electron-withdrawing (EWG) substituents with a neg. mesomeric effect, e.g. carboxyl (-COOH) and nitrile (-CN), favor iodines in ortho and para positions to act as halogen-bond donors. On the other hand, electron-donating (EDG) substituents, such as amino (-NH2), hydroxy (-OH), and methoxy (-OCH3) groups, which have a pos. mesomeric effect, increase the ability of m-iodines to act as halogen bond donors. Furthermore, EWG and EDG substituents with stronger mesomeric effects have a greater effect on the XB donor ability of the iodide substituents. Such a correlation is reflected in the size of the σ hole on the iodine atoms. Thus, the σ holes on o- and p-iodine atoms are larger than on m-iodine atoms in the presence of an EWG, making o- and p-iodines favorable XB donors. Similarly, the size of the σ hole on m-iodines is larger than those on o- and p-iodines in the presence of an EDG, causing m-iodines to favor XB donor behavior. This is confirmed by our MEP calculations, in which the size of the σ hole is expressed by the value of the maximum electrostatic potential (VS,max), being a maximum in the case of strong EWG substituents and a min. in the case of strong EDG substituents.3-Iodophenol(cas: 626-02-8Name: 3-Iodophenol) was used in this study.

3-Iodophenol(cas: 626-02-8) 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.Name: 3-Iodophenol

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

《Cobalt-Catalyzed Selective Unsymmetrical Dioxidation of gem-Difluoroalkenes》 was published in Journal of Organic Chemistry in 2020. These research results belong to Orsi, Douglas L.; Douglas, Justin T.; Sorrentino, Jacob P.; Altman, Ryan A.. Quality Control of 3-Iodophenol The article mentions the following:

Gem-Difluoroalkenes represent valuable synthetic handles for organofluorine chem.; however, most reactions of this substructure proceed through reactive intermediates prone to eliminate a fluorine atom and generate monofluorinated products. Taking advantage of the distinct reactivity of gem-difluoroalkenes, we present a cobalt-catalyzed regioselective unsym. dioxygenation of gem-difluoroalkenes using phenols and mol. oxygen, which retains both fluorine atoms and provides β-phenoxy-β,β-difluorobenzyl alcs. Mechanistic studies suggest that the reaction operates through a radical chain process initiated by Co(II)/O2/phenol and quenched by the Co-based catalyst. This mechanism enables the retention of both fluorine atoms, which contrasts most transition-metal-catalyzed reactions of gem-difluoroalkenes that typically involve defluorination. The experimental process involved the reaction of 3-Iodophenol(cas: 626-02-8Quality Control of 3-Iodophenol)

3-Iodophenol(cas: 626-02-8) belongs to organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.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.Quality Control of 3-Iodophenol

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

《Balancing Charge Transfer and Frenkel Exciton Coupling Leads to Excimer Formation in Molecular Dimers: Implications for Singlet Fission》 was published in Journal of Physical Chemistry A in 2020. These research results belong to Bae, Youn Jue; Shimizu, Daiki; Schultz, Jonathan D.; Kang, Gyeongwon; Zhou, Jiawang; Schatz, George C.; Osuka, Atsuhiro; Wasielewski, Michael R.. Formula: C6H4BrI The article mentions the following:

Photoexcitation of mol. chromophore aggregates can form excimer states that play a significant role in photophys. processes such as charge and energy transfer as well as singlet fission. An excimer state is commonly defined as a superposition of Frenkel exciton and charge transfer states. The dynamics were studied of excimer formation and decay in π-stacked 9,10-bis(phenylethynyl)anthracene (BPEA) covalent dimers appended to a xanthene spacer, where the electronic coupling between the 2 BPEA mols. is adjusted by changing their longitudinal mol. slip distances. Using exciton coupling calculations, the authors quantify the relative contributions of Frenkel excitons and charge transfer states and find that there is an upper and lower threshold of the charge transfer contribution for efficient excimer formation to occur. Knowing these thresholds can aid the design of mol. aggregates that optimize singlet fission. In addition to this study using 1-Bromo-4-iodobenzene, there are many other studies that have used 1-Bromo-4-iodobenzene(cas: 589-87-7Formula: C6H4BrI) 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,dibromostyrenesFormula: C6H4BrI

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

《A Mild and Versatile Friedel-Crafts Methodology for the Diversity-Oriented Synthesis of Redox-Active 3-Benzoylmenadiones with Tunable Redox Potentials》 was published in Chemistry – A European Journal in 2020. These research results belong to Cotos, Leandro; Donzel, Maxime; Elhabiri, Mourad; Davioud-Charvet, Elisabeth. COA of Formula: C7H5IO2 The article mentions the following:

A series of highly diversified 3-aroylmenadiones I [R = 4-F, 4-CF3, 3-NO2, etc.] was prepared by a new Friedel-Crafts acylation variant/oxidative demethylation strategy. A mild and versatile acylation was performed between 1,4-dimethoxy-2-methylnaphthalene and various activated/deactivated benzoic and heteroaromatic carboxylic acids, in the presence of mixed trifluoroacetic anhydride and triflic acid, at room temperature and in air. The 1,4-dimethoxy-2-methylnaphthalene-derived benzophenones II were isolated in high yield, and submitted to oxidative demethylation with cerium ammonium nitrate to produce 3-aroylmenadiones I. All 1,4-naphthoquinone derivatives were investigated as redox-active electrophores by cyclic voltammetry. The electrochem. data recorded for 3-acylated menadiones were characterized by a second redox process, the potentials of which cover a wide range of values (500 mV). These data emphasize the ability of the generated structural diversity at the 3-aroyl chain of these electrophores to fine-tune their corresponding redox potentials. These properties were of significance in the context of antimalarial drug development and understanding of the mechanism of bioactivation/action. The experimental part of the paper was very detailed, including the reaction process of 4-Iodobenzoic acid(cas: 619-58-9COA of Formula: C7H5IO2)

4-Iodobenzoic acid(cas: 619-58-9) belongs to organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.COA of Formula: C7H5IO2Iodo 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.

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

In 2019,Polymers (Basel, Switzerland) included an article by Zhang, Mingjing; Zhu, Liangjian; Guo, Pengzhi; Wang, Xunchang; Tong, Junfeng; Zhang, Xiaofang; Jia, Yongjian; Yang, Renqiang; Xia, Yangjun; Wang, Chenglong. Product Details of 516-12-1. The article was titled 《Effect of flank rotation on the photovoltaic properties of dithieno[2,3-d:2′,3′-d′]benzo [1,2-b:4,5-b′]dithiophene-based narrow band gap copolymers》. The information in the text is summarized as follows:

Side chain engineering has been an effective approach to modulate the solution processability, optoelectronic properties and miscibility of conjugated polymers (CPs) for organic/polymeric photovoltaic cells (PVCs). As compared with the most commonly used method of introducing alkyl chains, the employment of alkyl-substituted aryl flanks would provide two-dimensional (2-D) CPs having solution processability alongside addnl. merits like deepened HOMO (HOMO) energy levels, increased absorption coefficient and charger transporting, etc. In this paper, the triple C≃C bond was used as conjugated linker to decrease the steric hindrance between the flanks of 4,5-didecylthien-2-yl (T) and dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene (DTBDT) core. In addition, an alternating CP derived from 4,5-didecylthien-2-yl-ethynyl (TE) flanked DTBDT, and 4,9-bis(4-octylthien-2-yl) naphtho[1,2-c:5,6-c′]bis[1,2,5]thiadiazole (DTNT), named as PDTBDT-TE-DTNT, was synthesized and characterized. As compared with the controlled PDTBDT-T-DTNT, which was derived from 4,5-didecylthien-2-yl flanked DTBDT and DTNT, the results for exciton dissociation probability, d. functional theory (DFT), time-resolved photoluminescence (PL) measurements, etc., revealed that the lower steric hindrance between TE and DTBDT might lead to the easier rotation of the TE flanks, thus contributing to the decrease of the exciton lifetime and dissociation probability, finally suppressing the short-circuit c.d. (JSC), etc., of the photovoltaic devices from PDTBDT-TE-DTNT. In the experimental materials used by the author, we found 1-Iodopyrrolidine-2,5-dione(cas: 516-12-1Product Details of 516-12-1)

1-Iodopyrrolidine-2,5-dione(cas: 516-12-1) is used in the preparation of vinyl sulfones from olefins and benzenesulfinic acid. It acts as a source for I+ and involved in Hunsdiecker reactions for the conversion of cinnamic acids, and propiolic acids to the corresponding alfa-halostyrenes and 1-halo-1-alkynes respectively. Product Details of 516-12-1

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

In 2019,Advanced Synthesis & Catalysis included an article by Zhou, Bingnan; Dong, Jun; Xu, Jiaxi. Safety of Trimethylsulfoxonium iodide. The article was titled 《Safe, Metal-Free and Direct Synthesis of Dialkyl Acylmethylidenehydrazine-1,1-dicarboxylates from Dimethylsulfoxonium Acylmethylides and Dialkyl Azodicarboxylates》. The information in the text is summarized as follows:

N-Acylhydrazones were versatile electrophiles for the synthesis of nitrogen-containing compounds Dialkyl acylmethylidenehydrazine-1,1-dicarboxylates are a class of N-acylhydrazones and were prepared efficiently from dimethylsulfoxonium acylmethylides and dialkyl azodicarboxylates. The reaction was temperature-controlled, generating tetraalkyl 3,6-diacyl-1,2,4,5-tetrazinane-1,2,4,5-tetracarboxylates as major products accompanied by dialkyl acylmethylidenehydrazine-1,1-dicarboxylates as byproducts at low temperature, or dialkyl acylmethylidenehydrazine-1,1-dicarboxylates only at high temperature The current direct synthetic method was a safe and transition-metal-free route for the synthesis of dialkyl acylmethylidenehydrazine-1,1-dicarboxylates. The experimental process involved the reaction of 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

In 2019,Chemistry – A European Journal included an article by Tahara, Takuma; Suzuki, Shuichi; Kozaki, Masatoshi; Shiomi, Daisuke; Sugisaki, Kenji; Sato, Kazunobu; Takui, Takeji; Miyake, Yota; Hosokoshi, Yuko; Nojiri, Hiroyuki; Okada, Keiji. Quality Control of 1,2-Diiodoethane. The article was titled 《Triplet Diradical-Cation Salts Consisting of the Phenothiazine Radical Cation and a Nitronyl Nitroxide》. The information in the text is summarized as follows:

The spin-spin and magnetic properties of two (nitronyl nitroxide)-(di-p-anisylamine-phenothiazine) diradical cation salts, (DAA-PTZ)+-NN·MBr4- (M = Ga, Fe), have been investigated. These diradical-cation species were prepared by the cross-coupling of iodophenothiazine DAA-PTZ-I with NN-AuPPh3 followed by oxidation with the thianthrenium radical cation (TA+·MBr4-). These salts are highly stable under aerobic conditions. For the GaBr4 salt, large ferromagnetic intramol. and small antiferromagnetic intermol. interactions (J1/kB=+320 K and J2/kB=-2 K, resp.) were observed The magnetic property of the Fe3+ salt was analyzed by using a six-spin model assuming identical intramol. exchange interaction (J3/kB=+320 K) and the other exchange interactions (J4/kB=-7 K and J5/kB=-4 K). A significant color change was observed in the UV/visible/NIR absorption spectra upon electrochem. oxidation of the doublet DAA-PTZ-NN to the triplet (DAA-PTZ)+-NN. In the experiment, the researchers used 1,2-Diiodoethane(cas: 624-73-7Quality Control of 1,2-Diiodoethane)

1,2-Diiodoethane(cas: 624-73-7) is one of organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond. 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.Quality Control of 1,2-Diiodoethane

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

In 2019,Organic Chemistry Frontiers included an article by Chen, Xiaoyan; Zhou, Hao; Chen, Zhiyuan. Safety of Methyl 2-Fluoro-5-iodobenzoate. The article was titled 《Pd/P/dba-Promoted cascade annulations to produce fused medium-sized sulfoximine polyheterocycles》. The information in the text is summarized as follows:

The Pd-catalyzed multicomponent reactions of NH-sulfoximines, Ph iodides and norbornadiene (NBD) were reported to chemoselectively produced fused medium-sized sulfoximine polyheterocycles in good to excellent yields. The addition of the dibenzylideneacetone (dba) ligand was found to be useful for this tandem annulation reaction. Under the optimized conditions, a broad range of 3D-type heterocyclic sulfoximines with good functional group tolerance were generated. In the experiment, the researchers used Methyl 2-Fluoro-5-iodobenzoate(cas: 625471-27-4Safety of Methyl 2-Fluoro-5-iodobenzoate)

Methyl 2-Fluoro-5-iodobenzoate(cas: 625471-27-4) belongs to organic iodides. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Safety of Methyl 2-Fluoro-5-iodobenzoate Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics.

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

In 2019,Journal of Organic Chemistry included an article by Xiang, Jia-Chen; Wu, Zhi-Jie; Gu, Qing; You, Shu-Li. Formula: C7H5IO. The article was titled 《Palladium-Catalyzed C-H Diarylation of Ferrocenecarboxylic Acids with Aryl Iodides》. The information in the text is summarized as follows:

Palladium-catalyzed C-H diarylation of ferrocenes is described. In the presence of 10 mol% Pd(OAc)2, direct C-H diarylation reactions of com. available ferrocenecarboxylic acid with aryl iodides proceeded smoothly to afford diarylated ferrocenes bearing a variety of functional groups in moderate to good yields. The carboxylic group could also act as a remote directing group to result in the third arylation on the other Cp ring of ferrocene.4-Iodobenzaldehyde(cas: 15164-44-0Formula: C7H5IO) was used in this study.

4-Iodobenzaldehyde(cas: 15164-44-0) is used in synthesis of 4-[2-(trimethylsilyl)ethynyl]benzaldehyde, 5,15-dimesityl-10-(3-[2-(trimethylsilyl)ethynyi]phenyl}-20-(4-iodophenyl)porphyrin, and 5,15-dimesityl-10-[3,5-bis{2-[4-(N,N’-difluoroboryl-1,9-dimethyidipyrrin-5-yl)-phenyl]ethynyl}phenyl]-20-(4-iodophenyl)porphyrin.Formula: C7H5IO

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

In 2019,Analyst (Cambridge, United Kingdom) included an article by Li, Yannan; Yang, Li; Du, Mengqi; Chang, Guanjun. Related Products of 619-58-9. The article was titled 《Rational design of a boron-dipyrromethene-based fluorescent probe for detecting Pd2+ sensitively and selectively in aqueous media》. The information in the text is summarized as follows:

A novel fluorescent probe for Pd2+ based on the BODIPY fluorophore exploiting the PET (Photoinduced Electron Transfer) mechanism was designed and successfully synthesized. The fluorescent probe 1 was prepared by introducing m-bisimidazolylbenzene which was connected by Ph acetylene to the BODIPY dye at the meso position. It exhibited a rapid response and high sensitivity and selectivity toward Pd2+. Probe 1 presented a rapid quenched fluorescence response in aqueous buffer media (pH 5.5) and the detection limit estimated from the titration results was 2.9 × 10-7 M. Meanwhile, other common metal ions did not interfere with the recognition process. The DFT calculation proved that coordination of bisimidazole ligands with Pd2+ effectively decreases the LUMO energy of m-bisimidazolylbenzene which was located between the HOMO and LUMO energies of the BODIPY dye leading to fluorescence quenching via the d-PET mechanism.4-Iodobenzoic acid(cas: 619-58-9Related Products of 619-58-9) was used in this study.

4-Iodobenzoic acid(cas: 619-58-9) belongs to organic iodides. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Related Products of 619-58-9 Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics.

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