Iodides-buliding-blocks

The direct iodination of polyalkylbenzenes bearing bulky groups was written by Suzuki, Hitomi;Nakamura, Kiyomi;Goto, Ryozo. And the article was included in Bulletin of the Chemical Society of Japan in 1966.COA of Formula: C10H12I2 This article mentions the following:

A number of polyalkylbenzenes, bearing bulky substituents, afforded mono-iodo derivatives in high yield when treated with iodine-HIO₄. HIO₄ proved to be the most effective of several oxidizing agents examnd.: Ag₂SO₄, AgClO₄, HgO, K₂S₂O₈, HIO₃, and ο-IC₆H₄OMe. The reaction also proceded smoothly to yield mono- and diiodo derivatives of some polymethylbenzenes, but tri- and tetraiodination of xylene was difficult to effect. In a typical preparation a mixture of 5.40 g. 5-tert-Bu-1,3-Me₂C₆H₃, 1.54 g. HIO₄.2H₂O, 3.39 g. iodine, and 20 ml. 10:2:0.3 AcOH-H₂O-H₂SO₄ was stirred 4 hrs. at 60-5°. The mixture was cooled and the solid product was crystallized from petr. ether to give 8.7 g. 4-tert-Bu-2,6-Me₂C₆H₂I, m. 59-60°. The iodine atom was assumed to enter the ring para to the tert-Bu group. A similar procedure afforded the following compounds in good yield (compound, reaction time, reaction temperature, m.p., and b.p./mm. given): 5-tert-Bu-2,3-Me₂C₆H₂I, 6-7 hrs., 60-5°,–, 146-7°/14; 6-tert-Bu-2,3,4-Me₃C₆HI, 6-7 hrs., 60-5°, 74-5°,–; 2,3,5,6-iso-Pr₄C₆HI, 30 hrs., 75-80°, 161-3°,–; 2,5-tert-Bu₂C₆H₃I, ∼30 hrs., 75-80°,–, 156-7°/13-14; 4,5-I₂-1,2-Me₂C₆H₂, 3-4 hrs., 70°, 93-4°,–; 2,5-I₂-1,4-Me₂C₆H₂, 3-4 hrs., 70°, 104-5°,–; diiodoprehnitene, 1.5 hrs., 70°, 190-1°,–; diiododurene, 1.5 hrs., 70°, 140-1°,–. Where necessary, compounds were purified by chromatography over alumina and structures were verified by ir spectral examination In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1COA of Formula: 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. 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: C10H12I2

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

Modular synthesis of helicene-like compounds based on the imidazolium motif was written by Cizkova, Martina;Saman, David;Koval, Dusan;Kasicka, Vaclav;Klepetarova, Blanka;Cisarova, Ivana;Teply, Filip. And the article was included in European Journal of Organic Chemistry in 2014.Synthetic Route of C3H2I2N2 This article mentions the following:

Straightforward synthesis of novel mono- and tricationic helical compounds based on the imidazolium core was developed. The synthetic route based on double [2+2+2] cycloaddition reactions of precursors with the imidazolium core motif is notably modular and reaches beyond established protocols used for the synthesis of imidazolium systems as well as beyond the reported protocols used to assemble compounds with helical frameworks. This approach opened rapid four-step access to a cationic species featuring nine ortho-annulated rings that represents the highest order helical nitrogen-based cationic system reported to date. The structure of 2 was confirmed by the single crystal x-ray diffraction anal. [monoclinic, space group C2/c, a 39.389(3), b 14.2400(12), c 17.8968(14) Å, β 114.276(3)°, V 9150.7(13) ų, Z 8]. The detailed crystallog. data were deposited at the Cambridge Crystallog. Data Center as supplementary publication number CCDC 955735. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Synthetic Route of C3H2I2N2).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) 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.Synthetic Route of C3H2I2N2

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

Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylsulfonium halides generated in situ was written by Baik, Woonphil;Luan, Wanqiang;Lee, Hyun Joo;Yoon, Cheol Hun;Koo, Sangho;Kim, Byeong Hyo. And the article was included in Canadian Journal of Chemistry in 2005.Related Products of 160938-18-1 This article mentions the following:

Halodimethylsulfonium halides, which were readily formed in situ from hydrohalic acids and DMSO, was a good nucleophilic halide. This activated nucleophilic halide rapidly converted aryldiazonium salt prepared in situ by the same hydrohalic acid and nitrite ion to aryl chlorides, bromides, or iodides in good yield. The combined action of nitrite ion and hydrohalic acid in DMSO was required for the direct transformation of aromatic amines, which resulted in the production of aryl halides. Substituted compounds with electron-donating or -withdrawing groups or sterically hindered aromatic amines were also smoothly transformed to the corresponding aromatic halides. The only observed byproduct was the deaminated arene. The isolated aryldiazonium salts can also be converted to the corresponding aryl halides using the halodimethylsulfonium halides. The present method offers a facile, one-step procedure for transforming aminoarenes to haloarenes and lacks the environmental pollutants that usually accompany the Sandmeyer reaction using copper halides. In the experiment, the researchers used many compounds, for example, 4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1Related Products of 160938-18-1).

4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1) 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.Related Products of 160938-18-1

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

Researches in stoichiometry. I. The heat of fusion of organic compounds was written by Timmermans, Jean. And the article was included in Bulletin des Societes Chimiques Belges in 1935.HPLC of Formula: 160938-18-1 This article mentions the following:

By means of the freezing curves of binary mixtures which proved to be ideal solutions, the following heats of fusion (in cal. per g.-mol.) were determined: o-C₆H₄Me 2300, p- 3100, o-BrC₆H₄Me 2300, p-3.500, o-O₂NC₆H₄CH₂Cl 4900, P- 5200, o-O₂NC₆H₄CHCl₂ 3850, m- 4800, p- 3850, o-BrC₆H₄OH 2700, m-ClC₆H₄CO₂H 5600, P-O₂NC₆H₄OH 3800, m- 4550, p-O₂NC₆H₄NH₂ 4800, P-O₂NC₆H₄NHOCH 7600, p-ClC₆H₄NHOCH 5400, m-O₂NC₆H₄NHOCCH₃ 5400, p-ClO₂SC₆H₄COCl 4800, p-C₆H₄(SO₂Cl)₂ 3500, p-MeC₆H₄SO₂Cl 5400, o-MeC₆H₄SO₂NH₂ 6700, p- 5850, 1,2,3-Cl₃C₆H₃ 4150, 1,3,5-Cl₃C₆H₃ 4150, p-O₂NC₆H₄I 6900, 1,2,4-Br₂C₆H₃NO₂ 3100, 1,2,4-dinitroanisole 3900, 2,3-Cl₂C₆H₃CO₂H 6700, 2,5- 6100, 4,2-nitrochlorotoluene 4400, 6,2- 3900, 5,2- 3350, 3,2-3650, 1,2,4-nitrobromotoluene 4800, 1,3,4- 3850, 4,3,1-fluorochloronitrobenzene 4950, 3,4,1- 4700, 3,6,1- 4300, 1,3,6-chloroiodonitrobenzene 4000, 1,3,4- 4200, 1,3,4-chloronitroaniline 6800, 1,3,6- 5500, 1,2,4- 5600, 1,2,5-6000, 1,4,3- 5300, 1,2,6- 4900, 1,3,4-chloronitroacetanilide 5200, 1,2,5-nitrosalicylic acid 7800, α-cymenesulfonamide 6400, β- 6600, 2,4,5-Br₃C₆H₂Me 5000, 2,3,4- 3900, 2,3,6-4600, 2,4,6- 4800, 3,4,5- 4700, α-trinitrotoluene 4100, γ-4100, 2,6-dinitro-p-dichlorobenzene 7500, 2,3- 4400, 4,6-dibromo-3-aminomethylbenzene 5600, 2,6- 3700, phthalic acid 12,500, 4-chloroacetanilide 6900, trinitro-m-xylene 9500, 2,4-dinitrophenetole 5300, β-naphthol 5400, 3-chloroacenaphthene 4100, C₅H₁₂ 2000, CHCl₃ 2280, CH₂Cl₂ 1000, MeCHCl₂ 1250, EtBr 1400, PrBr 1560, BuBr 1600, iso-BuBr 600, tert-BuCl 500, PhF 1950, PhCl 1800, PhBr 2000, CS₂ 1350, methylal 1900, MeCOEt 1780, propionic acid 1800, isobutyric acid 1200, isovaleric acid 1750, valeric acid 1850, MeO₂CH 1800, EtO₂CH 2200, MeCN 2130, PrCN 1200, EtCN 1450, valeronitrile 1130, m-toluidine 930. Tentative correlations are appended. In the experiment, the researchers used many compounds, for example, 4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1HPLC of Formula: 160938-18-1).

4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1) 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.HPLC of Formula: 160938-18-1

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

Palladium-catalyzed C(sp³)-H arylation of lactic acid: efficient synthesis of chiral β-aryl-α-hydroxy acids was written by Chen, Kai;Li, Xin;Zhang, Shuo-Qing;Shi, Bing-Feng. And the article was included in Organic Chemistry Frontiers in 2016.Recommanded Product: 4-Iodo-1,2-dimethoxybenzene This article mentions the following:

Pd-catalyzed enantioselective arylation of lactic acid substrates employing 8-aminoquinoline as the directing group was reported. The protocol was found to be compatible with a broad range of synthetically useful functional groups, thus providing a practical route to chiral aryl-alkoxy-N-(quinolinyl)propanamides, e.g., I. Further, the new reaction was also applied to the synthesis of pharmaceutically important α-hydroxy acids, such as LY519818 and tesaglitazar. 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. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. 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: 4-Iodo-1,2-dimethoxybenzene

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

Palladium-catalyzed synthesis of ammonium sulfinates from aryl halides and a sulfur dioxide surrogate. A gas- and reductant-free process was written by Emmett, Edward J.;Hayter, Barry R.;Willis, Michael C.. And the article was included in Angewandte Chemie, International Edition in 2014.Safety of 3-Iodobenzo[b]thiophene This article mentions the following:

Described herein is a simple reaction system consisting of the sulfur dioxide surrogate DABSO, triethylamine, and a palladium(0) catalyst for effective conversion of a broad range of aryl and heteroaryl halides into the corresponding ammonium sulfinates. Key features of this gas- and reductant-free reaction include the low loadings of palladium (1 mol%) and ligand (1.5 mol%) which can be employed, and the use of iso-Pr alc. as both a solvent and formal reductant. The ammonium sulfinate products are converted in situ into a variety of sulfonyl-containing functional groups, including sulfones, sulfonyl chlorides, and sulfonamides. © Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Safety of 3-Iodobenzo[b]thiophene).

3-Iodobenzo[b]thiophene (cas: 36748-88-6) 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. 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 3-Iodobenzo[b]thiophene

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

Highly Efficient and Chemoselective Reduction of Nitroarenes Using Hybrid Ni@g-C₃N₄ as Reusable Catalyst was written by Payra, Soumen;Banerjee, Subhash. And the article was included in ChemistrySelect in 2019.SDS of cas: 160938-18-1 This article mentions the following:

Hybrid Ni@g-C₃N₄-catalyzed highly chemoselective reduction of nitroarenes to anilines with high turnover frequency was demonstrated using NaBH₄ as source of hydrogen. Here, g-C₃N₄ provided excellent stability to Ni(0) nanoparticles on its nitrogen rich surface and also facilitated the dissociation of NaBH₄ resulting formation of active Ni-H⁺ and Ni-H^– via cooperative effect. In the experiment, the researchers used many compounds, for example, 4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1SDS of cas: 160938-18-1).

4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1) 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.SDS of cas: 160938-18-1

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

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

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