Category: iodides-buliding-blocks

Bergman cycloaromatization of imidazole-fused enediynes: the remarkable effect of N-aryl substitution was written by Zhao, Zhengrong;Peng, Yunshan;Dalley, N. Kent;Cannon, John F.;Peterson, Matt A.. And the article was included in Tetrahedron Letters in 2004.Recommanded Product: 4,5-Diiodo-1H-imidazole This article mentions the following:

A series of N-aryl-substituted ‘imidazole-fused’ (Z) 3-ene-1,5-diynes, e.g., I, was prepared and kinetic parameters for their Bergman cycloaromatization reactivities were determined N-Arylation enhanced rates relative to N-alkyl derivatives by up to sevenfold (ANOVA p<0.0001). The greatest enhancement was exhibited by I. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Recommanded Product: 4,5-Diiodo-1H-imidazole).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) 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.Recommanded Product: 4,5-Diiodo-1H-imidazole

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

Ir^III-Catalyzed Selective ortho-Monoiodination of Benzoic Acids with Unbiased C-H Bonds was written by Weis, Erik;Johansson, Magnus J.;Martin-Matute, Belen. And the article was included in Chemistry – A European Journal in 2020.COA of Formula: C7H4BrIO2 This article mentions the following:

An iridium-catalyzed selective ortho-monoiodination of benzoic acids with two equivalent C-H bonds was presented. A wide range of electron-rich and electron-poor substrates underwent the reaction under mild conditions, with >20:1 mono/di selectivity. Importantly, the C-H iodination occurred selectively ortho to the carboxylic acid moiety in substrates bearing competing coordinating directing groups. The reaction was performed at room temperature and no inert atm. or exclusion of moisture was required. Mechanistic investigations revealed a substrate-dependent reversible C-H activation/protodemetalation step, a substrate-dependent turnover-limiting step and the crucial role of the AgI additive in the deactivation of the iodination product towards further reaction. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-iodobenzoic acid (cas: 503821-94-1COA of Formula: C7H4BrIO2).

3-Bromo-2-iodobenzoic acid (cas: 503821-94-1) 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–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.COA of Formula: C7H4BrIO2

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

Copper-Catalyzed Cross-Coupling of Functionalized Alkyl Halides and Tosylates with Secondary and Tertiary Alkyl Grignard Reagents was written by Ren, Peng;Stern, Lucas-Alexandre;Hu, Xile. And the article was included in Angewandte Chemie, International Edition in 2012.Application In Synthesis of 1-Bromo-4-(2-iodoethyl)benzene This article mentions the following:

A highly efficient method for the cross-coupling of non-activated and functionalized alkyl halides and tosylates with secondary and tertiary alkyl Grignard reagents has been developed. The copper-based method is remarkably practical and general. The wide scope, and especially the tolerance to a large number of important yet sensitive functional groups, make this method attractive for the streamlined synthesis of functional mols. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9Application In Synthesis of 1-Bromo-4-(2-iodoethyl)benzene).

1-Bromo-4-(2-iodoethyl)benzene (cas: 85356-68-9) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. 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.Application In Synthesis of 1-Bromo-4-(2-iodoethyl)benzene

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

A Modular Access to (±)-Tubocurine and (±)-Curine – Formal Total Synthesis of Tubocurarine was written by Otto, Nicola;Ferenc, Dorota;Opatz, Till. And the article was included in Journal of Organic Chemistry in 2017.SDS of cas: 2314-37-6 This article mentions the following:

Two consecutive Cu-catalyzed Ullmann-type C-O couplings permitted the first successful entry towards the curare alkaloids (±)-tubocurine and (±)-curine. Starting from vanillin, the synthetic sequence comprises of 15 linear steps and includes a total of 24 transformations. In addition, the total synthesis of tubocurine represents a formal total synthesis of the famous arrow poison alkaloid tubocurarine. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6SDS of cas: 2314-37-6).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.SDS of cas: 2314-37-6

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

Chlorination of iodophenols. V. m-Iodophenol was written by Buchan, Samuel;McCombie, Hamilton. And the article was included in Journal of the Chemical Society in 1932.Application of 289039-26-5 This article mentions the following:

M-IC₆H₄OH (I) in CCl₄ and Cl give a series of unstable iododichlorides and ring-substituted decomposition products very similar to those obtained from the p- and o-isomers (C. A. 25, 1504). I gives an acetate, m. 38°; the iododichloride, m. 91-2° (decomposition), decomposes over 7 days. The benzyl ether m. 52°; iododichloride, m. 70° (decomposition), decomposes over 2 days. Benzoate, m. 72-3°; iododichloride, m. 106° (decomposition), stable. p-Toluenesulfonate, m. 60-1°; iododichloride, m. 97-9° (decomposition), stable. Et carbonate, b₁₁, 163-4°; iododichloride, m. 79-80° (decomposition), stable for 4 months. Iodophenyl carbonate, m. 141°; bis(iododichloride), m. 115° (decomposition), stable. Me ether, b₁₄ 123°; iododichloride, m. 74° (decomposition), very unstable. Et ether, b₁₅ 133-4°, iododichloride, m. 64° (decomposition), unstable. Allyl ether, b₁₁ 154-6°. Dibromopropyl ether, oily; iododichloride, m. 78° (decomposition), decomposes overnight. Phenylcarbamate, m. 138°; iododichloride, m. 120° (decomposition), moderately stable. 3-Iododiphenyl ether, b₁₄ 185°; iododichloride, m. 58°, decomposes over 2 days. ω-3′-Iodophenoxyacetophenone, m. 104°; iododichloride, m. 94°, decomposes over a period of several days. I in CCl₄ and Cl give an iododichloride, which gives with KI and AcOH 6-chloro-3-iodophenol, m. 56°; its acetate b₁₁ 149° (iododichloride, m. 89° (decomposition), decomposes after 2 days); the benzyl ether b₁₁ 250-60° (iododichloride, m. 72° (decomposition), decomposes after 2 days). 2,4-I(O₂N)C₆H₃NH₂ gives 4-chloro-3-iodophenol, m. 78°. Chlorination of I in CCl₄ at 0° gives an iododichloride, m. 59°, which decomposes to give 4,6-dichloro-3-iodophenol (II), m. 104°; its iododichloride, m. 68-9° (decomposition), decomposes to give 2,4,6-trichloro-3-iodophenol (III), m. 104°. II yields an acetate, m. 95° (iododichloride, m. 104° (decomposition), stable). Benzyl ether, m. 82° (iododichloride, m. 86° (decomposition), decomposes after several days). III gives a benzyl ether, m. 80-1°). Neither III nor its derivatives yield iododichlorides. Chlorination of I at 60-70° in CCl₄ gives almost pure III; further chlorination gives the tetra-Cl derivative and Cl₅C₆OH. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-iodophenol (cas: 289039-26-5Application of 289039-26-5).

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

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

Novel cyanocombretastatins as potent tubulin polymerisation inhibitors was written by Jalily, Pouria H.;Hadfield, John A.;Hirst, Nicholas;Rossington, Steven B.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Electric Literature of C8H7IO2 This article mentions the following:

A series of novel cyanocombretastatins bearing a 3,4,5-trimethoxyphenyl moiety combined with a variety of substituted Ph rings, were synthesized and their antitumor activity was evaluated. The Z-cyanocombretastatins were synthesized in a one-step protocol in high purity and yield. Fluoro, bromo, iodo, and derivatives with boronic acid and an ethyne function at meta position of the B ring were synthesized. In vitro MTT bioassays against human chronic myelogenous leukemia (K562) and transfected breast adenocarcinoma (MDA NQO1) cell lines, revealed promising IC₅₀ inhibitory values in nanomolar range (<50 nM). Introduction of a nitrile function on the olefinic bond not only increased the cytotoxicity of the less active Z-isomers but rendered the analogs as moderate to potent inhibitors of tubulin polymerization comparable to that of CA-4 (IC₅₀ = 2.2 μM). Thus, compound I (IC₅₀ = 6.7 μM) was identified as a lead candidate for a further evaluation. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Electric Literature of C8H7IO2).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) 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. 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.Electric Literature of C8H7IO2

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

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide was written by Boehm, Philip;Roediger, Sven;Bismuto, Alessandro;Morandi, Bill. And the article was included in Angewandte Chemie, International Edition in 2020.Recommanded Product: 4-Iodo-1,2-dimethoxybenzene This article mentions the following:

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined exptl. and computational studies support a reaction mechanism involving in situ generation of CO. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Recommanded Product: 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. 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.Recommanded Product: 4-Iodo-1,2-dimethoxybenzene

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

Synthesis and Biological Profiling of Pyrazolo-Fused 7-Deazapurine Nucleosides was written by Fleuti, Marianne;Bartova, Katerina;Slavetinska, Lenka Postova;Tloust’ova, Eva;Tichy, Michal;Gurska, Sona;Pavlis, Petr;Dzubak, Petr;Hajduch, Marian;Hocek, Michal. And the article was included in Journal of Organic Chemistry in 2020.Related Products of 34091-51-5 This article mentions the following:

A series of 8-substituted 1-methyl-1,4-dihydropyrazolo[3′,4′:4,5]pyrrolo[2,3-d]pyrimidine (methylpyrazolo-fused 7-deazapurine) ribonucleosides has been designed and synthesized. Two synthetic approaches to the key heterocyclic aglycon I, (i) a six-step classical heterocyclization starting from 5-chloro-1-methyl-4-nitropyrazole and (ii) a three-step cross-coupling and cyclization approach starting from the zinc 4,6-dichloropyrimidine, gave comparable total yield of 18% vs. 13%. The glycosylation of I was attempted by three different methods but only the Vorbruggen silyl-base protocol was efficient and stereoselective to give desired β-anomeric nucleoside intermediate. Its nucleophilic substitutions or cross-coupling reactions at position 8 and deprotection of the sugar moiety gave eight derivatives of pyrazolo-fused deazapurine ribonucleosides, e.g. II, some of which were weakly fluorescent. Me, amino and methylsulfanyl derivatives exerted sub-micromolar cytotoxic effects in vitro against a panel of cancer and leukemia cell lines, as well as antiviral effect against hepatitis C virus in the replicon assay. In the experiment, the researchers used many compounds, for example, 5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5Related Products of 34091-51-5).

5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5) 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–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Related Products of 34091-51-5

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

Convenient Access to Arylated Spirocyclic Bisphosphonates was written by Lord, Taylor M.;Casino, Stephanie L.;Hartzell, Susan E.;Garcia, Kevin J.;Pike, Robert D.;Stockland, Robert A. Jr.. And the article was included in ChemistrySelect in 2016.Category: iodides-buliding-blocks This article mentions the following:

The synthesis of P-arylated spirocyclic bisphosphonates is described. The title compounds were generated through a process that combined transesterification with a palladium catalyzed P-arylation. The cross-coupling step could be carried out at room temperature using aryl iodides, while analogous reactions involving aryl bromides required heating. Nitrogen, oxygen, and sulfur containing heterocycles were also successfully incorporated into the framework. Using this approach 20 new arylated compounds were generated bearing a range of electrophiles and functional groups. For the more reactive aryl iodides, the catalyst loading could be decreased to 0.3 % Pd per P-H group in scaled-up versions of the method. The two-step process does not require the use of chlorophosphorus reagents. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Category: iodides-buliding-blocks).

3-Iodobenzo[b]thiophene (cas: 36748-88-6) 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. 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.Category: iodides-buliding-blocks

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

Silicon-Directed Oxa-Pictet-Spengler Cyclization and an Unusual Dimerization of 2-Trimethylsilanyl Tryptophols was written by Zhang, Xuqing;Li, Xiaojie;Lanter, James C.;Sui, Zhihua. And the article was included in Organic Letters in 2005.SDS of cas: 220185-63-7 This article mentions the following:

The tetrahydropyrano[3,4-b]indoles I (n = 1, 2; R¹ = H, CN, Cl, NO₂, F, CF₃, CO₂Me; R² = H, CF₃, Cl; R³ = Me; R⁴ = Me, MeS, EtS, BnS) were synthesized from 2-(2-trimethylsilanyl-1H-indol-3-yl)alkanols II and various ketones or aldehydes through silicon-directed oxa-Pictet-Spengler cyclizations. An unusual reaction led to the dimeric products III when some of II was treated with acetone using BF₃ as the catalyst. In the experiment, the researchers used many compounds, for example, 4,5-Dichloro-2-iodoaniline (cas: 220185-63-7SDS of cas: 220185-63-7).

4,5-Dichloro-2-iodoaniline (cas: 220185-63-7) 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. 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.SDS of cas: 220185-63-7

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