Month: January 2023

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 In the above 3 phenols the 3-Cl had been replaced by OH.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

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

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

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

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

Rapid aerobic iodination of arenes mediated by hypervalent iodine in fluorinated solvents was written by Iskra, Jernej;Murphree, S. Shaun. And the article was included in Tetrahedron Letters in 2017.Computed Properties of C8H9IO2 This article mentions the following:

Arenes such as 1,3,5-trimethoxybenzene, 4-tert-butylanisole, 1,2,4,5-tetramethylbenzene, etc. were rapidly converted to their corresponding iodides RI (R = 2-nitro-5-methylphenyl, 2-methyl-4-t-butylphenyl, 2,4,6-trimethylphenyl, etc.) by aerobic oxidative iodination at room temperature on treatment with iodine and catalytic quantities of nitrous acid in a fluorinated solvent. Dichloroiodic acid is proposed as the actual iodination reagent. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Computed Properties of C8H9IO2).

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. 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.Computed Properties of C8H9IO2

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

Structure-Kinetic Profiling of Haloperidol Analogues at the Human Dopamine D₂ Receptor was written by Fyfe, Tim J.;Kellam, Barrie;Sykes, David A.;Capuano, Ben;Scammells, Peter J.;Lane, J. Robert;Charlton, Steven J.;Mistry, Shailesh N.. And the article was included in Journal of Medicinal Chemistry in 2019.Application In Synthesis of 1,2-Difluoro-3-iodobenzene This article mentions the following:

Haloperidol is a typical antipsychotic drug (APD) associated with an increased risk of extrapyramidal side-effects (EPS) and hyperprolactinemia relative to atypical APDs such as clozapine. Both drugs are dopamine D₂ receptor (D₂R) antagonists, with contrasting kinetic profiles. Haloperidol displays fast association/slow dissociation at the D₂R whereas clozapine exhibits relatively slow association/fast dissociation Recently, the authors have provided evidence that slow dissociation from the D₂R predicts hyperprolactinemia, whereas fast association predicts EPS. Unfortunately, clozapine can cause severe side-effects independent of its D₂R action. The results suggest an optimal kinetic profile for D₂R antagonist APDs that avoids EPS. To begin exploring this hypothesis, the authors conducted a structure-kinetic relationship study of haloperidol and reveal that subtle structural modifications dramatically change binding kinetic rate constants, affording compounds with a clozapine-like kinetic profile. Thus, optimization of these kinetic parameters may allow development of novel APDs based on the haloperidol scaffold with improved side-effect profiles. In the experiment, the researchers used many compounds, for example, 1,2-Difluoro-3-iodobenzene (cas: 64248-57-3Application In Synthesis of 1,2-Difluoro-3-iodobenzene).

1,2-Difluoro-3-iodobenzene (cas: 64248-57-3) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.Application In Synthesis of 1,2-Difluoro-3-iodobenzene

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

7-halogenated 7-deazapurine 2′-deoxyribonucleosides related to 2′-deoxyadenosine, 2′-deoxyxanthosine, and 2′-deoxyisoguanosine: syntheses and properties was written by Seela, Frank;Xu, Kuiying. And the article was included in Helvetica Chimica Acta in 2008.Related Products of 1012785-51-1 This article mentions the following:

A series of 7-fluorinated 7-deazapurine 2′-deoxyribonucleosides related to 2′-deoxyadenosine, 2′-deoxyxanthosine, and 2′-deoxyisoguanosine as well as intermediates, e.g. I, were synthesized. The 7-fluoro substituent was introduced in 2,6-dichloro-7-deaza-9H-purine with Selectfluor. Apart from 2,6-dichloro-7-fluoro-7-deaza-9H-purine, the 7-chloro compound was formed and used for the glycosylation reaction; the separation of the 7-fluoro from the 7-chloro compound was performed on the level of the unprotected nucleosides. Other halogen substituents were introduced with N-halogenosuccinimides. The 2′-deoxyisoguanosine derivative I was prepared from 2-chloro-7-fluoro-7-deaza-2′-deoxyadenosine via a photochem. induced nucleophilic displacement reaction. The pK_a values of the halogenated nucleosides were determined ¹³C-NMR chem.-shift dependencies of C(7), C(5), and C(8) were related to the electronegativity of the 7-halogen substituents. In aqueous solution, 7-halogenated 2′-deoxyribonucleosides show an approx. 70% S population. In the experiment, the researchers used many compounds, for example, 2,4-Dichloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (cas: 1012785-51-1Related Products of 1012785-51-1).

2,4-Dichloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (cas: 1012785-51-1) 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. 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.Related Products of 1012785-51-1

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

Enantioselective Copper-Catalyzed Formal [2+1] and [4+1] Annulations of Diynes with Ketones via Carbonyl Ylides was written by Qi, Lin-Jun;Li, Cui-Ting;Huang, Zheng-Qi;Jiang, Jia-Tian;Zhu, Xin-Qi;Lu, Xin;Ye, Long-Wu. And the article was included in Angewandte Chemie, International Edition in 2022.Synthetic Route of C8H9IO2 This article mentions the following:

Carbonyl ylides have proven to be powerful synthons for the efficient construction of various valuable O-heterocycles, and the formation of carbonyl ylides by the reaction of metal carbenes with carbonyls has attracted increasing attention over the past decades. However, a catalyst-controlled highly enantioselective reaction of carbonyl ylides from metal carbenes is extremely challenging. Herein, a novel copper-catalyzed asym. formal [2+1] and [4+1] annulations of diynes with ketones via carbonyl ylides is reported. Importantly, this protocol not only represents the first example of successful asym. epoxidation via carbonyl ylides, but also constitutes the first reaction of vinyl cations with carbonyl compounds This method leads to the divergent, practical and atom-economical synthesis of a range of chiral oxiranes and dihydrofurans in moderate to excellent yields with generally excellent enantioselectivities and diastereoselectivities via remote-stereocontrol strategy. 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. 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–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.Synthetic Route of C8H9IO2

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

Stereocontrolled synthesis of unnatural cyclic dipeptides containing an L-valine unit was written by Balducci, Daniele;Grandi, Alessandro;Porzi, Gianni;Sandri, Sergio. And the article was included in Tetrahedron: Asymmetry in 2005.Safety of 1-Chloro-4-iodobutane This article mentions the following:

Stereoselective synthesis of unusual nonproteinogenic dipeptides I (Y = C:CH₂, R¹ = CO₂Et, R² = H; Y = C:CH₂, R¹ = Me, R² = CO₂Et; Y = CH₂CH₂, R¹ = CO₂Et, R² = H; Y = CH₂CH₂, R¹ = Me, R² = CO₂H; H Y = o-C₆H₄, R¹ = Me, R² = CO₂H), containing an L-valine unit and a cyclic unnatural α-amino acid, has been accomplished starting from the L-valine derived chiral synthon II via alkylation with dihalo derivatives as a key step. The absolute configurations of the new stereocentres were assigned on the basis of ¹H NMR spectra. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Safety 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. 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.Safety of 1-Chloro-4-iodobutane

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