Tag: 200-300

Pd^II-catalyzed monoselective ortho halogenation of C-H bonds assisted by counter cations: a complementary method to directed ortho lithiation was written by Mei, Tian-Sheng;Giri, Ramesh;Maugel, Nathan;Yu, Jin-Quan. And the article was included in Angewandte Chemie, International Edition in 2008.Quality Control of 2-Chloro-6-iodobenzoic acid This article mentions the following:

The yield and selectivity of monoselective ortho halogenation of benzoic acid derivatives were improved greatly by using tetraalkyl ammonium salts as additives. These effects are attributed to the influence of counter cations. The halogenated products are versatile intermediates for the construction of substituted aromatic compounds In the experiment, the researchers used many compounds, for example, 2-Chloro-6-iodobenzoic acid (cas: 13420-63-8Quality Control of 2-Chloro-6-iodobenzoic acid).

2-Chloro-6-iodobenzoic acid (cas: 13420-63-8) 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. 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.Quality Control of 2-Chloro-6-iodobenzoic acid

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

Visible-Light-Enabled Ph₃P/LiI-Promoted Tandem Radical Trifluoromethylation/Cyclization/Iodination of 1,6-Enynes with Togni’s Reagent was written by Liu, Hui;Fan, Xu;Hu, Jinkai;Ma, Tongtong;Wang, Feng;Yang, Jinhui;Li, Dianjun. And the article was included in Journal of Organic Chemistry in 2022.Application of 207115-22-8 This article mentions the following:

The visible-light-induced Ph₃P/LiI-promoted intermol. cascade trifluoromethyl radical addition/5-exo-dig cyclization/iodination of 1,6-enynes R¹CCCH₂XCH₂C(R²)=CH₂ [R¹ = 4-chlorophenyl, thiophen-2-yl, naphthalen-1-yl, etc.; R² = H, Me, Ph, COOEt; X = O, N(Ts), N(Boc)]/2-CCR³C₆H₅-4-R⁴C₆H₃OCH=CH₂ (R³ = H, 4-Me, 3-Cl 4-Br, etc.; R⁴ = H, Me, Br) with Togni’s reagent using LiI as the iodine source without the need of the transition metal, oxidant, and base were reported. This reaction promises to be a useful method for the preparation of trifluoromethyl-substituted and vinyl C-I bond-containing pyrrolidines I and benzofuran products II with good regioselectivity and functional-group tolerance under ambient conditions. 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. 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. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Application of 207115-22-8

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

Ir^III-Catalyzed Selective ortho-Monoiodination of Benzoic Acids with Unbiased C-H Bonds was written by Weis, Erik;Johansson, Magnus J.;Martin-Matute, Belen. And the article was included in Chemistry – A European Journal in 2020.Electric Literature of C7H4ClIO2 This article mentions the following:

An iridium-catalyzed selective ortho-monoiodination of benzoic acids with two equivalent C-H bonds was presented. A wide range of electron-rich and electron-poor substrates underwent the reaction under mild conditions, with >20:1 mono/di selectivity. Importantly, the C-H iodination occurred selectively ortho to the carboxylic acid moiety in substrates bearing competing coordinating directing groups. The reaction was performed at room temperature and no inert atm. or exclusion of moisture was required. Mechanistic investigations revealed a substrate-dependent reversible C-H activation/protodemetalation step, a substrate-dependent turnover-limiting step and the crucial role of the AgI additive in the deactivation of the iodination product towards further reaction. In the experiment, the researchers used many compounds, for example, 3-Chloro-2-iodobenzoic acid (cas: 123278-03-5Electric Literature of C7H4ClIO2).

3-Chloro-2-iodobenzoic acid (cas: 123278-03-5) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. 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 C7H4ClIO2

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

Novel imidazole-based histamine H₃ antagonists was written by Jablonowski, Jill A.;Ly, Kiev S.;Bogenstaetter, Michael;Dvorak, Curt A.;Boggs, Jamin D.;Dvorak, Lisa K.;Lord, Brian;Miller, Kirsten L.;Mazur, Curt;Wilson, Sandy J.;Lovenberg, Timothy W.;Carruthers, Nicholas I.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2009.Quality Control of 1-Chloro-4-iodobutane This article mentions the following:

A novel series of imidazole containing histamine H₃ receptor ligands, i.e. I, were investigated and found to be potent functional antagonists. After improving the stability of these mols. towards liver microsomes, these compounds were found to have no appreciable affinity for CYP P450s. Subsequent in vivo experiments showed significant brain uptake of (4-chloro-phenyl)-[2-(1-isopropyl-piperidin-4-ylmethoxy)-3-methyl-3H-imidazol-4-yl]-methanone I. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Quality Control of 1-Chloro-4-iodobutane).

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. 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.Quality Control of 1-Chloro-4-iodobutane

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

New insights in the structure-activity relationships of 2-phenylamino-substituted benzothiopyrano[4,3-d]pyrimidines as kinase inhibitors was written by Salerno, Silvia;Garcia-Argaez, Aida Nelly;Barresi, Elisabetta;Taliani, Sabrina;Simorini, Francesca;La Motta, Concettina;Amendola, Giorgio;Tomassi, Stefano;Cosconati, Sandro;Novellino, Ettore;Da Settimo, Federico;Marini, Anna Maria;Dalla Via, Lisa. And the article was included in European Journal of Medicinal Chemistry in 2018.Name: 4-Iodo-1,2-dimethoxybenzene This article mentions the following:

Inhibition of angiogenesis via blocking vascular endothelial growth factor receptor (VEGFR) signaling pathway emerged as an established approach in anticancer therapy. So far, many monoclonal antibodies and ATP-competitive small mol. inhibitors have been clin. validated and approved. In this study, structure-activity relationships (SAR) within the 2-phenylamino-substituted benzothiopyrano[4,3-d]pyrimidine class of kinase inhibitors were further refined by the synthesis and biol. evaluation of new compounds 1-21 featuring different substitution patterns on the pendant Ph moiety, combined with H, OCH₃, or Cl at 8-position. Most compounds showed a promising human kinase insert domain receptor (KDR) inhibition profile, with IC₅₀ values in the submicromolar/low nanomolar range, and promising antiproliferative activity on human umbilical vein endothelial cells (HUVECs) as well as on a panel of three human tumor cell lines. The angio-kinase selectivity profile was assessed for the most promising compound 16 against a set of six human kinases. Finally, computational studies allowed clarifying at mol. level the interaction pattern established by the compounds with KDR, highlighting key stable cation-π interactions, and thus providing the basis for further designing novel inhibitors. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Name: 4-Iodo-1,2-dimethoxybenzene).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.Name: 4-Iodo-1,2-dimethoxybenzene

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

Nickel-Catalyzed Asymmetric Reductive 1,2-Carboamination of Unactivated Alkenes was written by He, Jun;Xue, Yuhang;Han, Bo;Zhang, Chunzhu;Wang, You;Zhu, Shaolin. And the article was included in Angewandte Chemie, International Edition in 2020.Category: iodides-buliding-blocks This article mentions the following:

Starting from diverse alkene-tethered aryl iodides and O-benzoyl-hydroxylamines, the enantioselective reductive cross-electrophilic 1,2-carboamination of unactivated alkenes was achieved using a chiral pyrox/nickel complex as the catalyst. This mild, modular, and practical protocol provides rapid access to a variety of β-chiral amines with an enantioenriched aryl-substituted quaternary carbon center in good yields and with excellent enantioselectivities. This process reveals a complementary regioselectivity when compared to Pd and Cu catalysis. In the experiment, the researchers used many compounds, for example, (5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2Category: iodides-buliding-blocks).

(5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2) 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. 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.Category: iodides-buliding-blocks

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

Sonogashira Reactions with Propyne: Facile Synthesis of 4-Hydroxy-2-methylbenzofurans from Iodoresorcinols was written by Berliner, Martin A.;Cordi, Eric M.;Dunetz, Joshua R.;Price, Kristin E.. And the article was included in Organic Process Research & Development in 2010.Related Products of 338454-02-7 This article mentions the following:

The Sonogashira reaction of terminal alkynes and ortho-halophenols with subsequent cyclization is a well-precedented method for the synthesis of substituted benzofurans. Here we describe the extension of this method to the coupling of 2-iodoresorcinols and terminal alkynes, including propyne, to give 4-hydroxy-2-substituted benzofurans. In particular, we describe the screening, method development, and scaleup of the reaction with propyne using standard hydrogenation equipment. In the experiment, the researchers used many compounds, for example, Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7Related Products of 338454-02-7).

Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7) 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.Related Products of 338454-02-7

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

Determination of volatile compounds in cider apple juices using a covalently bonded ionic liquid coating as the stationary phase in gas chromatography was written by Pello-Palma, Jairo;Gonzalez-Alvarez, Jaime;Gutierrez-Alvarez, Maria Dolores;Dapena de la Fuente, Enrique;Mangas-Alonso, Juan Jose;Mendez-Sanchez, Daniel;Gotor-Fernandez, Vicente;Arias-Abrodo, Pilar. And the article was included in Analytical and Bioanalytical Chemistry in 2017.Product Details of 10297-05-9 This article mentions the following:

A chromatog. method for the separation of volatile compounds in Asturian cider apple juices has been developed. For this separation purpose, a monocationic imidazolium-based ionic liquid bearing a reactive terminal iodine atom was synthesized by a quaternization-anion exchange chem. sequence. Next, the gas chromatog. (GC) stationary phase was prepared by covalently linking the imidazolium monolith to the reactive silanol groups of the inner capillary wall at 70 °C. This coated GC column exhibited good thermal stability (290 °C), as well as good efficiency (2000 plates/m) in the separation of volatile compounds from Asturian apple cider juices, and was characterized using the Abraham solvation parameter model. The intra-day and inter-day precision of the chromatog. method was evaluated, obtaining relative standard deviations from 3.7 to 12.9% and from 7.4 to 18.0%, resp. Furthermore, recoveries from 82.5 to 122% were achieved. [Figure not available: see fulltext.]. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Product Details of 10297-05-9).

1-Chloro-4-iodobutane (cas: 10297-05-9) 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. 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.Product Details of 10297-05-9

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

Dative Directing Group Effects in Ti-Catalyzed [2+2+1] Pyrrole Synthesis: Chemo- and Regioselective Alkyne Heterocoupling was written by Chiu, Hsin-Chun;See, Xin Yi;Tonks, Ian A.. And the article was included in ACS Catalysis in 2019.Synthetic Route of C6H4BrIO This article mentions the following:

Transient dative substrate-Ti interactions have been found to play a key role in controlling the regioselectivity of alkyne insertion and [2+2] cycloaddition in Ti-catalyzed [2+2+1] pyrrole synthesis and Ti-catalyzed alkyne hydroamination. TMS-protected alkynes with pendent Lewis basic groups can invert the regioselectivity of TMS-protected alkyne insertion, leading to the selective formation of highly substituted 3-TMS pyrroles. The competency of various potential directing groups was investigated, and it was found that the directing-group effect can be tuned by modifying the catalyst Lewis acidity, the directing-group basicity, or the directing-group tether length. Dative directing-group effects are unexplored with Ti catalysts, and this study demonstrates the potential power of dative substrate-Ti interactions in tuning selectivity. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Synthetic Route of C6H4BrIO).

4-Bromo-2-iodophenol (cas: 207115-22-8) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. 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.Synthetic Route of C6H4BrIO

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

N-Iodosuccinimide (NIS) in Direct Aromatic Iodination was written by Bergstroem, Maria;Suresh, Ganji;Naidu, Veluru Ramesh;Unelius, C. Rikard. And the article was included in European Journal of Organic Chemistry in 2017.Application of 5460-32-2 This article mentions the following:

N-Iodosuccinimide (NIS) in pure trifluoroacetic acid (TFA) offers a time-efficient and general method for the iodination of a wide range of mono- and disubstituted benzenes at room temperature, as demonstrated in this paper. The starting materials were generally converted into mono-iodinated products in less than 16 h at room temperature, without byproducts. A few deactivated substrates needed addition of sulfuric acid to increase the reaction rate. Another exception was methoxybenzenes that preferentially were iodinated by NIS in acetonitrile with only catalytic amounts of TFA. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Application 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. 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 5460-32-2

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