Category: iodides-buliding-blocks

Ni-Catalyzed Sonogashira Coupling of Nonactivated Alkyl Halides: Orthogonal Functionalization of Alkyl Iodides, Bromides, and Chlorides was written by Vechorkin, Oleg;Barmaz, Delphine;Proust, Valerie;Hu, Xile. And the article was included in Journal of the American Chemical Society in 2009.Category: iodides-buliding-blocks This article mentions the following:

Ni-catalyzed Sonogashira coupling of nonactivated, β-H-containing alkyl halides, including chlorides, is reported. The coupling is tolerant to a wide range of functional groups, including ether, ester, amide, nitrile, keto, heterocycle, acetal, and aryl halide, in both coupling partners. The coupling can be selective for a specific C-X bond (X = I, Br, Cl) and allows for orthogonal functionalization of alkyl halides with multiple reactive sites. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Category: iodides-buliding-blocks).

1-Chloro-4-iodobutane (cas: 10297-05-9) 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.Category: iodides-buliding-blocks

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

Selectively Substituted Thiophenes and Indoles by a Tandem Palladium-Catalyzed Multicomponent Reaction was written by Mitsudo, Koichi;Thansandote, Praew;Wilhelm, Thorsten;Mariampillai, Brian;Lautens, Mark. And the article was included in Organic Letters in 2006.SDS of cas: 36748-88-6 This article mentions the following:

A variety of di- and trisubstituted thiophenes were synthesized by a one-pot Pd-catalyzed ortho-alkylation sequence terminated by either Heck or C-H coupling. Thus, reaction of 3-iodothiophene with BuI and H₂C:CHCO₂CMe₃ in acetonitrile containing Pd(OAc)₂, tri-2-furylphosphine, norbornene, and Cs₂CO₃ at 80° for 20 h gave 91% [(butoxycarbonyl)vinyl]thiophene I. Initial results toward the functionalization of indoles were also presented. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6SDS of cas: 36748-88-6).

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. 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.SDS of cas: 36748-88-6

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

Studies of biologically active quinazolinones: synthesis of some newer variously substituted 4-quinazolinones as antifertility agents was written by Shukla, J. S.;Saxena, Shradha. And the article was included in Journal of the Indian Chemical Society in 1979.Related Products of 20776-54-9 This article mentions the following:

In view of the diverse biol. activities associated with quinazolinones, some substituted quinazolinones I (R = 2-Cl, 2-MeO, 4-NO₂; R¹ = H, Br; R² = H, Br, iodo; R³ = 2-pyridyl, 2-thiazolyl) have been synthesized starting from the corresponding anthranilic acids and RC₆H₄OCH₂COCl followed by aminolysis. In the experiment, the researchers used many compounds, for example, 2-Amino-4-iodobenzoic acid (cas: 20776-54-9Related Products of 20776-54-9).

2-Amino-4-iodobenzoic acid (cas: 20776-54-9) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Related Products of 20776-54-9

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

Precise electro-reduction of alkyl halides for radical defluorinative alkylation was written by Yan, Xingxiu;Wang, Shengchun;Liu, Zhao;Luo, Yujie;Wang, Pengjie;Shi, Wenyan;Qi, Xiaotian;Huang, Zhiliang;Lei, Aiwen. And the article was included in Science China: Chemistry in 2022.Formula: C4H8ClI This article mentions the following:

A precise electro-reduction strategy for radical defluorinative alkylation towards the synthesis of gem-difluoroalkenes from α-trifluoromethylstyrenes was reported. According to the redox-p.d. of the radical precursors, direct or indirect electrolysis was resp. adopted to realize the precise reduction An easy-to-handle, catalyst- and metal-free condition was developed for the reduction of alkyl radical precursors that are generally easier to be reduced than α-trifluoromethylstyrenes, while a novel electro-Ni-catalytic system was established for the electro-reduction of alkyl bromides or chlorides towards the electrochem. synthesis of gem-difluoroalkenes. The merit of this protocol was exhibited by its mild conditions, wide substrate scope, and scalable preparation Mechanistic studies and DFT calculations proved that the coordination of α-trifluoromethylstyrenes to Ni-catalyst prevents the direct reduction of the alkene and, in turn, promotes the activation of alkyl bromide through halogen atom transfer mechanism. 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. 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.Formula: C4H8ClI

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

The action of sodium methoxide on some derivatives of o-dichlorobenzene was written by Kraay, G. M.. And the article was included in Diss. Amsterdam in 1926.Quality Control of 2-Chloro-5-iodophenol This article mentions the following:

The derivatives studied represent o-C₆H₄Cl₂ in which a p-H atom is replaced by F, Cl, Br, I, NO₂, SO₃H, Me, CO₂H, NH₂, OH, NO, CN, CHO and COPh. These substances were treated with NaOMe in MeOH at 180° and in most cases the products isolated and identified in order to determine where the replacement occurred. It appears that a halogen is first replaced by OMe to yield an anisole, which then reacts with a 2nd mol. of NaOMe giving the Na salt of a phenol and Me₂O. New substances of the above type are 3,4-dichlorofluorobenzene (I), b. 171°, prepared in 88% purity by treating the diazotized Cl₂C₅H₃NH₂ with 55% HF, distilling with steam and fractionating several times; 3,4-dichloroiodobenzene (II), m. 30.5°, in 83% yield by the Sandmeyer reaction with KI; 3,4-dichlorobenzonitrile (III), m. 72.1°, in 57% yield by the Sandmeyer reaction with CuCN; 3,4-dichloronitrosobenzene (IV), m. 88°, by reduction of the corresponding nitro derivative with NaSH to 3,4-dichlorophenylhydroxylamine (73% yield), m. 75° (decomposition), which readily oxidizes in the air to 3,3′,4,4′-tetrachloroazoxybenzene (V), m. 139-9.5°, and then oxidation with K₂Cr₂O₇ (yield 50%); and 3,4-dichlorobenzyl alc. (VI), m. 38°, from the corresponding aldehyde by the Cannizzaro reaction. New products obtained by treatment of p-substituted o-C₆H₄Cl₂ with NaOMe are 3-hydroxy-4-chlorotoluene (VII), m. 46°, from the Cl₂C₆H₃Me; 2-chloro-5-bromophenol (VIII), m. 57°, from the C₆H₃Cl₂Br; and 2-chloro-5-iodophenol (IX), m. 56.5°, from II. VIII was also prepared by diazotization of 2,5-ClBrC₆H₃NH₂. 2-Chloro-5-iodonitrobenzene, m. 74.5°, was prepared in 86% yield by treating the diazotized Cl(O₂N)C₆H₃NH₂ with KI; reduction of this with TiCl₂ gave 84% of 2-chloro-5-iodoaniline, m. 61.5°, and this in turn when treated with HNO₂ gave IX. VII was also prepared in 78% yield from the chlorotoluidine and HNO₂. In the above 3 phenols the 3-Cl had been replaced by OH. The 2 following reactions carried out in the same manner showed a replacement elsewhere; Iâ†?,4-Cl₂C₆H₃OH, 3,4-Cl₂C₆H₃SO₃Hâ†?,4-Cl(HO)C₅H₃SO₃H. In the case of 3,4-Cl₂C₆H₃OH no reaction occurred, III gave unidentified products of saponification, IV became reduced to V, 3,4-Cl₂C₆H₃COPh was recovered for the most part unchanged, and 3,4-Cl₂C₆H₃CHO probably underwent the Cannizzaro reaction. Selective replacements of the halogens are discussed from the standpoint of polarity. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-iodophenol (cas: 289039-26-5Quality Control of 2-Chloro-5-iodophenol).

2-Chloro-5-iodophenol (cas: 289039-26-5) 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.Quality Control of 2-Chloro-5-iodophenol

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

Indium-Mediated Synthesis of Heterobiaryls was written by Font-Sanchis, Enrique;Cespedes-Guirao, F. Javier;Sastre-Santos, Angela;Fernandez-Lazaro, Fernando. And the article was included in Journal of Organic Chemistry in 2007.Quality Control of 5-Iodo-1-methyl-1H-pyrazole This article mentions the following:

The palladium-mediated coupling reaction between triorganoindium reagents and heteroaryl iodides is extended to the synthesis of heterobiaryls, e.g., I. Both electron-rich and electron-poor heterocycles can act as the organic electrophile or as the organoindium derivative In the experiment, the researchers used many compounds, for example, 5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5Quality Control of 5-Iodo-1-methyl-1H-pyrazole).

5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5) 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.Quality Control of 5-Iodo-1-methyl-1H-pyrazole

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

Total synthesis of keramamides A and L from a common precursor by late-stage indole synthesis and configurational revision was written by Junk, Lukas;Kazmaier, Uli. And the article was included in Angewandte Chemie, International Edition in 2018.SDS of cas: 289039-26-5 This article mentions the following:

The marine natural products keramamide A and L, members of the class of anabaenopeptin-type peptides, were synthesized for the first time by a convergent and flexible route. The installation of the substituted tryptophan moieties was accomplished at the very end of the synthesis on the cyclic peptides, and thus enabled the synthesis of both natural products from one common precursor. The preparation of several epimers clearly indicates that the originally proposed relative configurations of both Keramamides A and L were not correct. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-iodophenol (cas: 289039-26-5SDS of cas: 289039-26-5).

2-Chloro-5-iodophenol (cas: 289039-26-5) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. 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.SDS of cas: 289039-26-5

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

Discovery and optimization of a novel CNS penetrant series of mGlu₄ PAMs based on a 1,4-thiazepane core with in vivo efficacy in a preclinical Parkinsonian model was written by Kent, Caitlin N.;Fulton, Mark G.;Stillwell, Kaylee J.;Dickerson, Jonathan W.;Loch, Matthew T.;Rodriguez, Alice L.;Blobaum, Anna L.;Boutaud, Olivier;Rook, Jerri L.;Niswender, Colleen M.;Conn, P. Jeffrey;Lindsley, Craig W.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2021.Application In Synthesis of 3-Fluoro-5-iodoaniline This article mentions the following:

A high throughput screen (HTS) identified a novel, but weak (EC₅₀ = 6.2μM, 97% Glu Max) mGlu₄ PAM chemotype based on a 1,4-thiazepane core, VU0544412. Reaction development and chem. optimization delivered a potent mGlu₄ PAM VU6022296 (EC₅₀ = 32.8 nM, 108% Glu Max) with good CNS penetration (K_p = 0.45, K_p,uu = 0.70) and enantiopreference. Finally, VU6022296 displayed robust, dose-dependent efficacy in reversing Haloperidol-Induced Catalepsy (HIC), a rodent preclin. Parkinson’s disease model. In the experiment, the researchers used many compounds, for example, 3-Fluoro-5-iodoaniline (cas: 660-49-1Application In Synthesis of 3-Fluoro-5-iodoaniline).

3-Fluoro-5-iodoaniline (cas: 660-49-1) 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. 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.Application In Synthesis of 3-Fluoro-5-iodoaniline

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

Efficient iodination of aromatic compounds using potassium ferrate supported on montmorillonite was written by Keipour, Hoda;Khalilzadeh, Mohammad A.;Mohtat, Bita;Hosseini, Abolfazl;Zareyee, Daryoush. And the article was included in Chinese Chemical Letters in 2011.Application In Synthesis of 4,5-Diiodo-1H-imidazole This article mentions the following:

Potassium ferrate impregnated on montmorillonite is a mild, cheap, and non-toxic reagent for the iodination of phenols, including naphthol, aromatic amines, and heterocyclic substrates in fair to excellent yields by a simple isolation procedure. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Application In Synthesis of 4,5-Diiodo-1H-imidazole).

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

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

Synthesis and in vivo brain distribution of carbon-11-labeled δ-opioid receptor agonists was written by Pichika, Rama;Jewett, Douglas M.;Sherman, Philip S.;Traynor, John R.;Husbands, Stephen M.;Woods, James H.;Kilbourn, Michael R.. And the article was included in Nuclear Medicine and Biology in 2010.Application of 77350-52-8 This article mentions the following:

Three new radiolabeled compounds, [¹¹C]SNC80 ((+)-4-[(αR)-α-{(2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl}]-3-[¹¹C]methoxybenzyl-N,N-diethylbenzamide), N,N-diethyl-4-(3-methoxyphenyl-1-[¹¹C]methylpiperidin-4-ylidenemethyl)benzamide and N,N-diethyl-4-[(1-[¹¹C]methylpiperidin-4-ylidene)phenylmethyl]benzamide, were prepared as potential in vivo radiotracers for the δ-opioid receptor. Each compound was synthesized by alkylation of the appropriate desmethyl compounds using [¹¹C]methyl triflate. In vivo biodistribution studies in mice showed very low initial brain uptake of all three compounds and no regional specific binding for [¹¹C]SNC80. A monkey positron emission tomog. study of [¹¹C]SNC80 confirmed low brain permeability and uniform regional distribution of this class of opioid agonists in a higher species. Opioid receptor ligands of this structural class are thus unlikely to succeed as in vivo radiotracers, likely due to efficient exclusion from the brain by the P-glycoprotein efflux transporter. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Application of 77350-52-8).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. 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.Application of 77350-52-8

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