Month: January 2023

Pd-Catalyzed ipso,meta-Dimethylation of ortho-Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source was written by Wu, Zhuo;Wei, Feng;Wan, Bin;Zhang, Yanghui. And the article was included in Journal of the American Chemical Society in 2021.Application In Synthesis of 4-Bromo-2-iodophenol This article mentions the following:

A Me group can have a profound impact on the pharmacol. properties of organic mols. Hence, developing methylation methods and methylating reagents is essential in medicinal chem. We report a palladium-catalyzed dimethylation reaction of ortho-substituted iodoarenes using di-Me carbonate as a Me source. In the presence of K₂CO₃ as a base, iodoarenes are dimethylated at the ipso- and meta-positions of the iodo group, which represents a novel strategy for meta-C-H methylation. With KOAc as the base, subsequent oxidative C(sp³)-H/C(sp³)-H coupling occurs; in this case, the overall transformation achieves triple C-H activation to form three new C-C bonds. These reactions allow expedient access to 2,6-dimethylated phenols, 2,3-dihydrobenzofurans, and indanes, which are ubiquitous structural motifs and essential synthetic intermediates of biol. and pharmacol. active compounds In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Application In Synthesis of 4-Bromo-2-iodophenol).

4-Bromo-2-iodophenol (cas: 207115-22-8) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Application In Synthesis of 4-Bromo-2-iodophenol

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

Generation and electrophilic substitution reactions of 3-lithio-2-methyleneaziridines was written by Montagne, Cyril;Prevost, Natacha;Shiers, Jason J.;Prie, Gildas;Rahman, Sabitur;Hayes, Jerome F.;Shipman, Michael. And the article was included in Tetrahedron in 2006.Application of 10297-05-9 This article mentions the following:

2-Methyleneaziridinyl anions can be produced by selective deprotonation of the parent aziridine at C-3 using sec-BuLi/TMEDA. Subsequent reaction with a wide variety of electrophiles including MeI, ICH₂CH₂CH₂CH₂Cl, PhCH₂Br, allyl bromide, Me₃SiCl, Bu₃SnCl, PhCHO, and Ph₂CO provides the corresponding C-3 substituted derivatives in moderate to good yields (43-91%). In the case of homochiral methyleneaziridines bearing an (S)-α-methylbenzyl group on nitrogen, high levels of diastereocontrol (up to 90% de) can be achieved in this lithiation/alkylation sequence. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Application of 10297-05-9).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. 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 10297-05-9

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

Chiral 2-endo-Substituted 9-Oxabispidines: Novel Ligands for Enantioselective Copper(II)-Catalyzed Henry Reactions was written by Breuning, Matthias;Hein, David;Steiner, Melanie;Gessner, Viktoria H.;Strohmann, Carsten. And the article was included in Chemistry – A European Journal in 2009.Product Details of 10297-05-9 This article mentions the following:

A flexible approach, applicable on a gram scale, to chiral 2-endo-substituted 9-oxabispidines I [R¹ = Et, i-Pr, cyclohexyl, Ph, R² = Me; R¹R² = (CH₂)₄] was developed. The key intermediate, a cis-configured 6-aminomethylmorpholine-2-carbonitrile II, was prepared from (R)-3-aminopropane-1,2-diol and 2-chloroacrylonitrile. The 2-endo substituent was introduced by Grignard addition, cyclization, and exo-selective reduction, thus furnishing the enantiomerically pure bi- and tricyclic 9-oxabispidines I in 19-59% yields. The CuCl₂ complex of the tricyclic 9-oxabispidine I [R¹R² = (CH₂)₄], which carries an 2-endo,N-annelated piperidine ring, is an excellent catalyst for enantioselective Henry reactions of aldehydes R³CHO (R³ = i-Bu, n-octyl, Ph, 4-O₂NC₆H₄, etc.) with nitromethane giving the S-configured β-nitro alcs. R³CH(OH)CH₂NO₂ in 91-98% ee (13 examples). Surprisingly, the analogous copper complexes of the bicyclic 9-oxabispidines I (R² = Me) delivered the enantiocomplementary R-configured products in 33-57% ee. The resp. transition states were discussed. 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 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.Product Details of 10297-05-9

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

Microwave assisted domino Heck cyclization and alkynylation: synthesis of alkyne substituted dihydrobenzofurans was written by Karu, Ramesh;Gedu, Satyanarayana. And the article was included in Green Chemistry in 2018.Quality Control of 4-Bromo-2-iodophenol This article mentions the following:

Microwave assisted domino intramol. Heck and Sonogashira coupling for the efficient synthesis of alkyne substituted dihydrobenzofurans is presented. Interestingly, the strategy showed broad substrate scope and was successful with protecting group free functionalities of acetylenes. Gratifyingly, all products were obtained, in excellent to near quant. yields, in a short span of time. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Quality Control of 4-Bromo-2-iodophenol).

4-Bromo-2-iodophenol (cas: 207115-22-8) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. 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 4-Bromo-2-iodophenol

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

Novel preparation of functionalized iodotetrahydronaphthyridine, iodoazaindoline, and iodotetrahydropyridoazepine systems was written by Nguyen, Hanh Nho;Wang, Zhan J.. And the article was included in Tetrahedron Letters in 2007.Related Products of 10297-05-9 This article mentions the following:

A novel method, which utilizes a key halogen dance step for the preparation of iodotetrahydronaphthyridine, iodoazaindoline, and iodotetrahydropyridoazepine ring-systems is described. A variety of transformations of the iodo-functional group are also reported to demonstrate the utility of this method. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Related Products of 10297-05-9).

1-Chloro-4-iodobutane (cas: 10297-05-9) 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. 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.Related Products of 10297-05-9

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

Application of organolithium compounds in organic synthesis. Part 19. Synthetic strategies based on aromatic metalation. A concise regiospecific synthesis of 3-halogenated picolinic and isonicotinic acids was written by Epsztajn, J.;Plotka, M. W.;Grabowska, A.. And the article was included in Synthetic Communications in 1997.Electric Literature of C6H4INO2 This article mentions the following:

The synthesis of the halogenated picolin- and isonicotinanilides I (R = Cl, Br, iodo, X = N, Y = CH; X = CH, Y = N) (II) via metalation (n-BuLi) of the anilides I (R = H) and then the reaction of the generated bis-lithiated anilides with halogenating agents (CCl₃-CCl₃, CH₂Br-CH₂Br, I₂) followed by subsequent acidic hydrolysis of II, as a way of regiospecific transformation of picolinic and isonicotinic acids into their C³-halogenated derivatives, is described. In the experiment, the researchers used many compounds, for example, 3-Iodopicolinic acid (cas: 73841-32-4Electric Literature of C6H4INO2).

3-Iodopicolinic acid (cas: 73841-32-4) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. 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.Electric Literature of C6H4INO2

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

Synthesis and evaluation of a ¹¹C-labelled angiotensin II AT₂ receptor ligand was written by Aberg, Ola;Stevens, Marc;Lindh, Jonas;Wallinder, Charlotta;Hall, Hakan;Monazzam, Azita;Larhed, Mats;Langstrom, Bengt. And the article was included in Journal of Labelled Compounds and Radiopharmaceuticals in 2010.Safety of N,N-Diethyl-4-iodobenzamide This article mentions the following:

Three ¹¹C-radiolabeled high-affinity nonpeptide AT₂ receptor-selective ligands were synthesized, and one of these was evaluated as positron emission tomog. (PET) tracer. The labeling reaction was performed via Pd(0)-mediated aminocarbonylation of the aryl iodide substrate using ¹¹CO as the labeled precursor. As an example, starting with 10.0 GBq ¹¹CO, 1.10 GBq of the product N-butoxycarbonyl-3-[4-(N-benzyl-[¹¹C]carbamoyl)phenyl]-5-isobutylthiophene-2-sulfonamide was obtained in 36% decay-corrected radiochem. yield (from ¹¹CO), 42 min from end of bombardment with a specific activity of 110 GBq μmol^-1. The N-isopropyl-[¹¹C]carbamoyl analog (radiochem. purity >95%) was studied employing autoradiog., organ distribution, and small animal PET. In vitro autoradiog. showed specific binding in the pancreas and kidney. Organ distribution in rats revealed a high uptake in liver, intestine, kidney, and adrenals. Small animal PET showed rapid and reversible uptake in the kidneys followed by accumulation in the urinary bladder suggesting fast renal excretion of the tracer. In addition, high accumulation was also seen in the liver. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Safety 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. 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.Safety of N,N-Diethyl-4-iodobenzamide

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

Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita was written by Chen, Xiulei;Zhou, Zhen;Li, Zhong;Xu, Xiaoyong. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2020.Product Details of 20776-54-9 This article mentions the following:

A series of novel 1,2,3-benzotriazin-4-one derivatives containing 4,5-dihydrothiazole-2-thiol I (R = H, 5-OMe, 7-F, 8-NO₂, etc.) was synthesized. The bioassay results showed that compounds I (R = 7-OMe, 6-NO₂, 7-Cl (A)) exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita at the concentration of 10.0 mg L^-1 in vivo. Compound (A) showed excellent nematicidal activity with inhibition 68.3% at a concentration of 1.0 mg L^-1. It suggested that the structure of 1,2,3-benzotriazin-4-one containing 4,5-dihydro-thiazole-2-thiol could be optimized further. In the experiment, the researchers used many compounds, for example, 2-Amino-4-iodobenzoic acid (cas: 20776-54-9Product Details of 20776-54-9).

2-Amino-4-iodobenzoic acid (cas: 20776-54-9) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. 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.Product Details of 20776-54-9

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

Azine and Diazine Functionalization Using 2,2,6,6-Tetramethylpiperidino-Based Lithium-Metal Combinations: Application to the Synthesis of 5,9-Disubstituted Pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidines was written by Marquise, Nada;Nguyen, Tan Tai;Chevallier, Floris;Picot, Laurent;Thiery, Valerie;Lozach, Olivier;Bach, Stephane;Ruchaud, Sandrine;Mongin, Florence. And the article was included in Synlett in 2015.COA of Formula: C4H2ClIN2 This article mentions the following:

The synthesis of triaryl methanols was investigated by reacting different 4-metalated 2-substituted pyrimidines with diaryl ketones, the latter being generated by deprotocupration-aroylation of azine and diazine substrates. Cyclization of the triaryl methanols thus obtained afforded pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidines, which were evaluated for kinase inhibition and antiproliferative activities in melanoma cells. In the experiment, the researchers used many compounds, for example, 2-Chloro-4-iodopyrimidine (cas: 395082-55-0COA of Formula: C4H2ClIN2).

2-Chloro-4-iodopyrimidine (cas: 395082-55-0) 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. 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.COA of Formula: C4H2ClIN2

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

Nickel-Catalyzed Asymmetric Hydrogenation of Cyclic Alkenyl Sulfones, Benzo[b]thiophene 1,1-Dioxides, with Mechanistic Studies was written by Liu, Gongyi;Tian, Kui;Li, Chenzong;You, Cai;Tan, Xuefeng;Zhang, Heng;Zhang, Xumu;Dong, Xiu-Qin. And the article was included in Organic Letters in 2021.Application In Synthesis of 4-Iodo-1,2-dimethoxybenzene This article mentions the following:

A highly efficient catalytic system based on the cheap transition metal nickel for the asym. hydrogenation of challenging cyclic alkenyl sulfones, 3-substituted benzo[b]thiophene 1,1-dioxides, was first successfully developed. A series of hydrogenation products, chiral 2,3-dihydrobenzo[b]thiophene 1,1-dioxides I [R = H, OMe; R¹ = Et, Ph, 2-MeC₆H₄, etc.] was obtained in high yields (95-99%) with excellent enantioselectivities (90-99% ee). According to the results of nonlinear effect studies, deuterium-labeling experiments, and DFT calculation investigations, a reasonable catalytic mechanism for this nickel-catalyzed asym. hydrogenation was provided, which displayed that the two added hydrogen atoms of the hydrogenation products could be from H₂ through the insertion of Ni-H and subsequent hydrogenolysis. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Application In Synthesis of 4-Iodo-1,2-dimethoxybenzene).

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. 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.Application In Synthesis of 4-Iodo-1,2-dimethoxybenzene

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