Month: February 2023

Synthesis of 2′-Substituted 4-Bromo-2,4′-bithiazoles by Regioselective Cross-Coupling Reactions was written by Bach, Thorsten;Heuser, Stefan. And the article was included in Journal of Organic Chemistry in 2002.Reference of 10297-05-9 This article mentions the following:

The synthesis of the title compounds [I; R = Bu, CH₂CHMe₂, CH₂CH₂Ph, (CH₂)₄Cl, CHMe₂, sec-Bu, Ph, C椤氬挵CMe₃, C椤氬挵Ph, etc.] was achieved in two steps starting from readily available 2,4-dibromothiazole (II). In a regioselective Pd(0)-catalyzed cross-coupling step, II was converted to a variety of 2-substituted 4-bromothiazoles (III, same R) (10 examples, 65-85% yield). Alkyl and aryl zinc halides were employed as nucleophiles to introduce an alkyl or aryl substituent. The Sonogashira protocol was followed to achieve an alkynyl-debromination. Bromo-lithium exchange at C-4 and subsequent transmetalation to zinc or tin converted the 4-bromothiazoles to carbon nucleophiles, which underwent a second regioselective cross-coupling with another equivalent of 2,4-dibromothiazole. The Negishi cross-coupling gave high yields of the 2′-alkyl-4-bromo-2,4′-bithiazoles (88-97%). The synthesis of the 2′-phenyl- and 2′-alkynyl-4-bromo-2,4′-bithiazoles required a Stille cross-coupling that did not proceed as smoothly as the Negishi cross-coupling (58-62% yield). The title compounds, which were accessible in total yields of 38-82%, are versatile building blocks for the synthesis of 2,4′-bithiazoles. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Reference 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閳ユ彂 bond is the weakest of the carbon閳ユ従alogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.Reference of 10297-05-9

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

A new, improved and convenient synthesis of 4H-cyclopenta[2,1-b:3,4-b’]-dithiophen-4-one was written by Brzezinski, Jacek Z.;Reynolds, John R.. And the article was included in Synthesis in 2002.Reference of 474416-61-0 This article mentions the following:

A new and efficient three-step synthesis of 4H-cyclopenta[2,1-b:3,4-b’]dithiophen-4-one is described. This was achieved by a one-pot, regiospecific synthesis of bis(2-iodo-3-thienyl)methanol, its subsequent oxidation to the bis(2-iodo-3-thienyl) ketone which after Ullmann coupling yielded the title compound In the experiment, the researchers used many compounds, for example, Bis(2-iodothiophen-3-yl)methanone (cas: 474416-61-0Reference of 474416-61-0).

Bis(2-iodothiophen-3-yl)methanone (cas: 474416-61-0) belongs to iodide derivatives. 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鑱砈mith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Reference of 474416-61-0

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

A palladium-catalyzed three-component cascade S-transfer reaction in ionic liquids was written by Li, Jianxiao;Wu, Yaodan;Hu, Miao;Li, Can;Li, Meng;He, Dandan;Jiang, Huanfeng. And the article was included in Green Chemistry in 2019.Product Details of 5460-32-2 This article mentions the following:

A palladium-catalyzed three component cascade S-transfer reaction of acetylenic oximes RCCC(R¹)=NOH (R = Ph, cyclopropyl, cyclohexyl, thiophen-3-yl, etc.; R¹ = Me, Ph, cyclohexyl, etc.) with aryl halides ArI (Ar = 4-methylphenyl, 4-methoxyphenyl, naphthalen-2-yl, thiophen-2-yl, etc.) using readily available Na₂S₂O₃ as an odorless sulfenylation reagent under aerobic conditions in ionic liquids was described. The present protocol features environmental friendliness, good functional group compatibility, odorless sulfenylation reagents, without any ligand or additive, and excellent atom and step economy. Remarkably, this cascade procedure will bring further late-stage modification for the construction of structurally complex isoxazole scaffolds I in synthetic and pharmaceutical chem. 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. 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. 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 5460-32-2

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

Metal-Free, Oxidant-Free, and Controllable Graphene Oxide Catalyzed Direct Iodination of Arenes and Ketones was written by Zhang, Jingyu;Li, Shiguang;Deng, Guo-Jun;Gong, Hang. And the article was included in ChemCatChem in 2018.Electric Literature of C8H5IS This article mentions the following:

A direct, metal-free, and oxidant-free method for the graphene oxide (GO)-catalyzed iodination of arenes and ketones with iodine in a neutral medium was explored. This iodination protocol was performed by using a simple technique to avoid the use of external metal catalysts and oxidants and harsh acidic/basic reaction conditions. In addition, by this method the degree of iodination could be controlled, and the reaction was scalable and compatible with air. This strategy opens a new field for GO-catalyzed chem. and provides an avenue for the convenient direct iodination of arenes and ketones. 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. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. The C閳ユ彂 bond is the weakest of the carbon閳ユ従alogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.Electric Literature of C8H5IS

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

Lewis Acid Catalyzed Formal Intramolecular [3 + 3] Cross-Cycloaddition of Cyclopropane 1,1-Diesters for Construction of Benzobicyclo[2.2.2]octane Skeletons was written by Ma, Weiwei;Fang, Jie;Ren, Jun;Wang, Zhongwen. And the article was included in Organic Letters in 2015.Quality Control of (5-Fluoro-2-iodophenyl)methanol This article mentions the following:

A novel Lewis acid catalyzed formal intramol. [3 + 3] cross-cycloaddition (IMCC) of cyclopropane 1,1-diesters has been successfully developed. This supplies an efficient and conceptually new strategy for construction of bridged bicyclo[2.2.2]octane skeletons I [R = Me, Et, Bn,etc]. This [3 + 3]IMCC could be run up to gram scale and from easily prepared starting materials. This [3 + 3]IMCC, together with our previously reported [3 + 2]IMCC strategy, can afford either the bicyclo[2.2.2]octane or bicyclo[3.2.1]octane skeletons from the similar starting materials by regulating the substituents on vinyl group. In the experiment, the researchers used many compounds, for example, (5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2Quality Control of (5-Fluoro-2-iodophenyl)methanol).

(5-Fluoro-2-iodophenyl)methanol (cas: 877264-43-2) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C閳ユ彂 bond. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons鑱砈mith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Quality Control of (5-Fluoro-2-iodophenyl)methanol

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

Iodothyronine Deiodinase Mimics. Deiodination of o,o’-Diiodophenols by Selenium and Tellurium Reagents was written by Vasil’ev, Andrei A.;Engman, Lars. And the article was included in Journal of Organic Chemistry in 1998.SDS of cas: 207115-22-8 This article mentions the following:

To better understand, and in the extension mimic, the action of the three selenium-containing iodothyronine deiodinases, o,o’-diiodophenols were reacted under acidic conditions with sodium hydrogen telluride, benzenetellurol, sodium hydrogen selenide, or benzeneselenol and under basic conditions with the corresponding deprotonated reagents. Sodium hydrogen telluride was found to selectively remove one iodine from a variety of 4-substituted o,o’-diiodophenols, including a protected form of thyroxine. Thus, it mimics the D1 variety of the iodothyronine deiodinases. Sodium telluride was a more reactive deiodinating agent toward o,o’-diiodophenols, often causing removal of both halogens. Benzenetellurol and sodium benzenetellurolate sometimes showed useful selectivity for monodeiodination. However, the products were often contaminated by small amounts of organotellurium compounds Sodium hydrogen selenide, sodium selenide, benzeneselenol, and sodium benzeneselenolate were essentially unreactive toward o,o’-diiodophenols. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8SDS of cas: 207115-22-8).

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. The C閳ユ彂 bond is the weakest of the carbon閳ユ従alogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.SDS of cas: 207115-22-8

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

ortho-Metalation of Unprotected 3-Bromo and 3-Chlorobenzoic Acids with Hindered Lithium Dialkylamides was written by Gohier, Frederic;Mortier, Jacques. And the article was included in Journal of Organic Chemistry in 2003.Recommanded Product: 503821-94-1 This article mentions the following:

Upon treatment of 3-chloro/bromobenzoic acids with hindered lithium dialkylamides (LDA or LTMP) at -50 鎺矯, lithium 3-chloro/bromo-2-lithiobenzoates are generated. These dianions can be trapped as such to afford after electrophilic quenching a variety of simple 2-substituted-3-chloro/bromobenzoic acids. The 3-bromo-2-lithiobenzoate is less stable than the 3-chloro analog and partly eliminates lithium bromide, thus setting free lithium 2,3- and 3,4-dehydrobenzoates that can be intercepted in situ with the hindered base. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-iodobenzoic acid (cas: 503821-94-1Recommanded Product: 503821-94-1).

3-Bromo-2-iodobenzoic acid (cas: 503821-94-1) 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.Recommanded Product: 503821-94-1

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

Efficient Copper-Catalyzed Trifluoromethylation of Aromatic and Heteroaromatic Iodides: The Beneficial Anchoring Effect of Borates was written by Gonda, Zsombor;Kovacs, Szabolcs;Weber, Csaba;Gati, Tamas;Meszaros, Attila;Kotschy, Andras;Novak, Zoltan. And the article was included in Organic Letters in 2014.Electric Literature of C6H4INO2 This article mentions the following:

Efficient copper-catalyzed trifluoromethylation of aromatic iodides was achieved with TMSCF₃ in the presence of tri-Me borate. The Lewis acid was used to anchor the in situ generated trifluoromethyl anion and suppress its rapid decomposition Broad applicability of the new trifluoromethylating reaction was demonstrated in the functionalization of different aromatic and heteroaromatic iodides. In the experiment, the researchers used many compounds, for example, 2-Iodopyridine-4-carboxylic acid (cas: 58481-10-0Electric Literature of C6H4INO2).

2-Iodopyridine-4-carboxylic acid (cas: 58481-10-0) 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. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Electric Literature of C6H4INO2

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

Nickel-Catalyzed Cross-Coupling between Functionalized Primary or Secondary Alkylzinc Halides and Primary Alkyl Halides was written by Jensen, Anne Eeg;Knochel, Paul. And the article was included in Journal of Organic Chemistry in 2002.COA of Formula: C4H8ClI This article mentions the following:

In the presence of Bu₄NI (3 equiv) and 4-fluorostyrene (20 mol %), unreactive primary and secondary alkylzinc iodides undergo nickel-catalyzed cross-couplings with various primary alkyl iodides or bromides. More reactive secondary dialkylzincs and the mixed zinc organometallics RZnTMSM undergo the cross-coupling reaction in the absence of Bu₄NI. The bicyclic secondary diorganozinc prepared via boron-zinc exchange reacts with high retention of configuration. Free NH-groups are tolerated in the cross-coupling allowing the synthesis of aminated products. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9COA of Formula: C4H8ClI).

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. 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.COA of Formula: C4H8ClI

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

Synthesis and SAR studies of novel heteroaryl fused tetracyclic indole-diamide compounds: Potent allosteric inhibitors of the hepatitis C virus NS5B polymerase was written by Ding, Min;He, Feng;Hudyma, Thomas W.;Zheng, Xiaofan;Poss, Michael A.;Kadow, John F.;Beno, Brett R.;Rigat, Karen L.;Wang, Ying-Kai;Fridell, Robert A.;Lemm, Julie A.;Qiu, Dike;Liu, Mengping;Voss, Stacey;Pelosi, Lenore A.;Roberts, Susan B.;Gao, Min;Knipe, Jay;Gentles, Robert G.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Category: iodides-buliding-blocks This article mentions the following:

Presented here are initial structure-activity relationship (SAR) studies on a series of novel heteroaryl fused tetracyclic indole-based inhibitors of the hepatitis C viral polymerase, NS5B. The introduction of alternative heterocyclic moieties into the indolo-fused inhibitor class significantly expands the reported SAR and resulted in the identification of pyridino analogs, typified by compounds I and II that displayed excellent potency against the NS5B polymerase of both HCV 1a and HCV 1b genotypes. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Category: iodides-buliding-blocks).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) 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. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Category: iodides-buliding-blocks

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