Category: iodides-buliding-blocks

Ligand-Enabled β-C-H Arylation of α-Amino Acids Using a Simple and Practical Auxiliary was written by Chen, Gang;Shigenari, Toshihiko;Jain, Pankaj;Zhang, Zhipeng;Jin, Zhong;He, Jian;Li, Suhua;Mapelli, Claudio;Miller, Michael M.;Poss, Michael A.;Scola, Paul M.;Yeung, Kap-Sun;Yu, Jin-Quan. And the article was included in Journal of the American Chemical Society in 2015.Synthetic Route of C8H9IO2 This article mentions the following:

Palladium-catalyzed β-C-H functionalizations of carboxylic acid derivatives using an auxiliary as a directing group have been extensively explored in the past decade. In comparison to the most widely used auxiliaries in asym. synthesis, the simplicity and practicality of the auxiliaries developed for C-H activation remains to be improved. The authors previously developed a simple N-methoxyamide auxiliary to direct β-C-H activation, albeit this system was not compatible with carboxylic acids containing α-hydrogen atoms. Herein, the authors report the development of a pyridine-type ligand that overcomes this limitation of the N-methoxyamide auxiliary, leading to a significant improvement of β-arylation of carboxylic acid derivatives, especially α-amino acids. The arylation using this practical auxiliary is applied to the gram-scale syntheses of unnatural amino acids, bioactive mols., and chiral bis(oxazoline) ligands. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Synthetic Route of C8H9IO2).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) 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.Synthetic Route of C8H9IO2

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

Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C-H Activation was written by Romanov-Michailidis, Fedor;Sedillo, Kassandra F.;Neely, Jamie M.;Rovis, Tomislav. And the article was included in Journal of the American Chemical Society in 2015.Related Products of 10297-05-9 This article mentions the following:

α,β-Unsaturated oxime pivalates are proposed to undergo reversible C(sp²)-H insertion with cationic Rh(III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to convert these mols. into piperidines, which are important structural components of numerous pharmaceuticals. Thus, e.g., heterocyclization of unsaturated oxime pivalate I with alkene II in presence of [Rh(MeCN)₃(C₅Me₄CF₃)](SbF₆)₂ afforded dihydropyridine III (99%). 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. 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.Related Products of 10297-05-9

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

P/N Heteroleptic Cu(I)-Photosensitizer-Catalyzed Deoxygenative Radical Alkylation of Aromatic Alkynes with Alkyl Aldehydes Using Dipropylamine as a Traceless Linker Agent was written by Bao, Hanyang;Zhou, Bingwei;Luo, Shu-Ping;Xu, Zheng;Jin, Hongwei;Liu, Yunkui. And the article was included in ACS Catalysis in 2020.Electric Literature of C8H5IS This article mentions the following:

A deoxygenative radical alkylation of aromatic alkynes with alkyl aldehydes for the preparation of allylarenes was successfully achieved. This transformation is accomplished through the reaction of alkyl aldehydes with alkynes in the presence of dipropylamine and Hantzsch ester catalyzed by a P/N heteroleptic Cu(I)-based photosensitizer under photoredox catalysis conditions. Preliminary mechanistic studies reveal that this aldehyde-alkyne coupling process comprises a regioselective radical addition of in-situ-generated alkyl-substituted α-amino radicals to alkynes with subsequent 1,5-proton transfer, C-N bond cleavage and concomitant isomerization of the resulting allyl radical species. Thus, in net result, dipropylamine serves as a traceless linker agent for the deoxygenative radical cross-coupling of alkyl aldehydes with alkynes under photoredox catalysis reaction conditions. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Electric Literature of C8H5IS).

3-Iodobenzo[b]thiophene (cas: 36748-88-6) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Electric Literature of C8H5IS

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

Active Molybdenum-Based Anode for Dehydrogenative Coupling Reactions was written by Beil, Sebastian B.;Mueller, Timo;Sillart, Sydney B.;Franzmann, Peter;Bomm, Alexander;Holtkamp, Michael;Karst, Uwe;Schade, Wolfgang;Waldvogel, Siegfried R.. And the article was included in Angewandte Chemie, International Edition in 2018.Product Details of 5460-32-2 This article mentions the following:

A new and powerful active anode system that can be operated in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) was discovered. In HFIP the Mo anode forms a compact, conductive, and electroactive layer of higher-valent Mo species. This system can replace powerful but stoichiometrically required Mo^V reagents for the dehydrogenative coupling of aryls. This electrolytic reaction is more sustainable and allows the conversion of a broad scope of activated arenes. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Product Details 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. 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 5460-32-2

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

Synthesis and antitumor activity of novel pyrimidinyl pyrazole derivatives. III. Synthesis and antitumor activity of 3-phenylpiperazinyl-1-trans-propenes was written by Naito, Hiroyuki;Ohsuki, Satoru;Atsumi, Ryo;Minami, Megumi;Mochizuki, Mineko;Hirotani, Kenji;Kumazawa, Eiji;Ejima, Akio. And the article was included in Chemical & Pharmaceutical Bulletin in 2005.Formula: C6H5FIN This article mentions the following:

A series of 3-[4-phenyl-1-piperazinyl]-1-[5-methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-1-trans-propenes, e.g., I, and related compounds were synthesized and evaluated by their cytotoxic activity against several tumor cell lines in vitro and in vivo antitumor activity against some tumor models when administered both i.p. and orally. Compounds with the 3-chloropyridin-2-yl group and the 3-fluoro-5-substituted phenylpiperazinyl group showed significantly potent cytotoxicity by in vitro testing. Among them, the 3-cyano-5-fluorophenyl derivative I exhibited potent antitumor activity against several tumor cells including human carcinoma without causing undesirable effects in mice. In the experiment, the researchers used many compounds, for example, 3-Fluoro-5-iodoaniline (cas: 660-49-1Formula: C6H5FIN).

3-Fluoro-5-iodoaniline (cas: 660-49-1) belongs to iodide derivatives. 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.Formula: C6H5FIN

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

Exploring influence of fluorine substitution on the strength and nature of halogen bond between iodobenzene and hydrogen cyanide was written by Naghani, Farhad Fereydooni;Emamian, Saeedreza;Zare, Karim. And the article was included in Journal of Physical Organic Chemistry in 2021.Safety of 1,2-Difluoro-3-iodobenzene This article mentions the following:

In the present study, the intermol. I … N halogen bond (XB) interaction between iodobenzene (IBZ) and its fluorinated derivatives (as Lewis acids LA 1 through LA 20) with HCN (as Lewis base LB) is theor. explored to shed light on the electronic nature and strength of the mentioned non-covalent interaction (NCI). The hydrogen atoms of Ph ring in IBZ were substituted by fluorine atom to probe different impacts of this atom. Such a substitution is paid attention from the number as well as the position of fluorine atoms points of view. Our analyses reveal that this XB interaction whose interaction energy spans a narrow range between 1.0 and 3.0 kcal·mol^-1 should be classified as a weak NCI. The symmetry-adapted perturbation theory (SAPT) anal. evidences that the I … N XB in the investigated binary complexes (BCs) is mainly dominated by electrostatic and dispersion interactions, and, in the meantime, induction interactions can safely be ignored. Among the many I … N XB descriptors, V_s,max, which corresponds to the most pos. value of electrostatic potential computed for the iodine atom in LAs, plays a key role. Indeed, such an easily and rapidly computable quantity (V_s,max) allows a sufficiently accurate prediction of interaction energy together with SAPT-derived components anal. to become feasible by a simple inclusion of V_s,max value within the numerous explored estimators. Although the strength of I … N XB interaction in the studied BCs is increased by an increase in the number of fluorine substituent, the position of fluorine atom cannot significantly alter the strength of the mentioned interaction. In the experiment, the researchers used many compounds, for example, 1,2-Difluoro-3-iodobenzene (cas: 64248-57-3Safety of 1,2-Difluoro-3-iodobenzene).

1,2-Difluoro-3-iodobenzene (cas: 64248-57-3) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. 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.Safety of 1,2-Difluoro-3-iodobenzene

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

Improved, acid-catalyzed iodinating procedures for activated aromatics with (diacetoxyiodo)benzene as the oxidant was written by Kryska, Anna;Skulski, Lech. And the article was included in Journal of Chemical Research, Synopses in 1999.HPLC of Formula: 3268-21-1 This article mentions the following:

Activated aromatics are effectively converted, at room temperature and within 15 min, into the corresponding mono-, di- or tri-iodinated products in anhydrous I₂-PhI(OAc)₂-AcOH-Ac₂O systems, acidified with catalytic amounts of concentrate H₂SO₄. In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1HPLC of Formula: 3268-21-1).

1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1) 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.HPLC of Formula: 3268-21-1

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

Robust Synthesis of Methyl 5-Chloro-4-fluoro-1H-indole-2-carboxylate: A Key Intermediate in the Preparation of an HIV NNRTI Candidate was written by Mayes, Benjamin A.;Chaudhuri, Narayan C.;Hencken, Christopher P.;Jeannot, Frederic;Latham, G. Mark;Mathieu, Steven;McGarry, F. Patrick;Stewart, Alistair J.;Wang, Jingyang;Moussa, Adel. And the article was included in Organic Process Research & Development in 2010.Recommanded Product: 4-Chloro-3-fluoro-2-iodoaniline This article mentions the following:

A synthetic preparation of Me 5-chloro-4-fluoro-1H-indole-2-carboxylate, a key intermediate towards phosphoindole inhibitors of HIV non-nucleoside reverse transcriptase, is described. The five-step synthesis involved Boc protection of the com. available 4-chloro-3-fluoroaniline and regioselective iodination at C-2. After facile Boc deprotection, cyclization of the resultant o-iodoaniline gave the corresponding 5-chloro-4-fluoroindole-2-carboxylic acid which was subsequently esterified to provide the target indole ester in 56% overall yield. Identification of 6-chloro-7-iodo-2(3H)-benzoxazolone as a significant side product in the iodination step led to the development of conditions which eliminated its formation in subsequent batches. Advantages of this alternative approach relative to existing methodologies include (1) potentially hazardous diazonium and azido species were not required, (2) regioisomeric products were not generated, and (3) chromatog. isolations were avoided, as all intermediates were easily crystallized As a result, the key indole ester was produced rapidly at 100-fold increased scale compared to previous reports with a 10-fold improvement in overall yield. In the experiment, the researchers used many compounds, for example, 4-Chloro-3-fluoro-2-iodoaniline (cas: 1018450-37-7Recommanded Product: 4-Chloro-3-fluoro-2-iodoaniline).

4-Chloro-3-fluoro-2-iodoaniline (cas: 1018450-37-7) 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. 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.Recommanded Product: 4-Chloro-3-fluoro-2-iodoaniline

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

Carboranes Increase the Potency of Small Molecule Inhibitors of Nicotinamide Phosphoribosyltranferase was written by Lee, Mark W.;Sevryugina, Yulia V.;Khan, Aslam;Ye, Shui Q.. And the article was included in Journal of Medicinal Chemistry in 2012.Formula: C4H8ClI This article mentions the following:

Herein we report the use of carboranes to significantly increase the potency of small mol. inhibitors of nicotinamide phosphoribosyltranferase (Nampt), an enzyme that is central to metabolism and cell survival. We compare the inclusion of carborane with other similarly sized substituents and demonstrate that, compared with their purely organic counterparts, these mols. exhibit up to 10-fold greater antiproliferative activity against cancer cells in vitro and a 100-fold increase in Nampt inhibition. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Formula: C4H8ClI).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. 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.Formula: C4H8ClI

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

A Domino Approach (Hydrolysis/Dehydrohalogenation/Heck Coupling) for the Synthesis of Styrene Sulfonate Salts was written by Prakash, G. K. Surya;Jog, Parag V.;Krishnan, Hema S.;Olah, George A.. And the article was included in Journal of the American Chemical Society in 2011.Formula: C10H12I2 This article mentions the following:

A domino approach of hydrolysis/dehydrohalogenation/Heck coupling was used to synthesize styrene sulfonate salts from iodoarenes and chloroethanesulfonyl chloride in good to excellent yields. Methodol. was applicable for heterocyclic as well as disubstituted iodoarenes. Some of the key features of this synthetic methodol. include the use of a phosphine-free catalytic system, water as an environmentally friendly solvent, short reaction times, and absence of additives. In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1Formula: C10H12I2).

1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1) 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. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Formula: C10H12I2

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