Tag: 200-300

Isopropanol and potassium tert-butoxide promoted intramolecular direct sp² C-H functionalization: an expedient synthesis of 1,2,3-triazole annulated chromens and quinolones was written by Mondal, Biplab;Roy, Brindaban. And the article was included in Tetrahedron Letters in 2015.Electric Literature of C6H4BrIO This article mentions the following:

A series of 1,2,3-triazole annulated chromen I (R¹ = H, 8-Me, 8-t-Bu, 8-Br, 6,8-di-Cl, 8-Cl, 8-CO₂Et; R² = Bn, 2-NO₂Bn, 1-octyl, 1-heptyl), and quinolone derivatives II (R³ = Me, Et, n-Bu) have been synthesized by means of direct sp² C-H functionalization in the presence of iso-propanol and potassium tert-butoxide. The reaction proceeds through homolytic aromatic substitution (HAS). This efficient as well as simple C-H functionalization methodol. offers a straightforward route to 1,2,3-triazole annulated oxygen and nitrogen heterocycles. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Electric Literature of C6H4BrIO).

4-Bromo-2-iodophenol (cas: 207115-22-8) 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. 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.Electric Literature of C6H4BrIO

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

Base- and Additive-Free Ir-Catalyzed ortho-Iodination of Benzoic Acids: Scope and Mechanistic Investigations was written by Erbing, Elis;Sanz-Marco, Amparo;Vazquez-Romero, Ana;Malmberg, Jesper;Johansson, Magnus J.;Gomez-Bengoa, Enrique;Martin-Matute, Belen. And the article was included in ACS Catalysis in 2018.Recommanded Product: 13420-63-8 This article mentions the following:

A protocol for the C-H activation/iodination of benzoic acids catalyzed by a simple iridium complex has been developed. The method described in this paper allows the ortho-selective iodination of a variety of benzoic acids under extraordinarily mild conditions in the absence of any additive or base in 1,1,1,3,3,3-hexafluoroisopropanol as the solvent. The iridium catalyst used tolerates air and moisture, and selectively gives ortho-iodobenzoic acids with high conversions. Mechanistic investigations revealed that an Ir(III)/Ir(V) catalytic cycle operates, and that the unique properties of HFIP enables the C-H iodination using the carboxylic moiety as a directing group. In the experiment, the researchers used many compounds, for example, 2-Chloro-6-iodobenzoic acid (cas: 13420-63-8Recommanded Product: 13420-63-8).

2-Chloro-6-iodobenzoic acid (cas: 13420-63-8) belongs to iodide derivatives. 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.Recommanded Product: 13420-63-8

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

Photocatalytic Oxidative Iodination of Electron-Rich Arenes was written by Narobe, Rok;Duesel, Simon J. S.;Iskra, Jernej;Koenig, Burkhard. And the article was included in Advanced Synthesis & Catalysis in 2019.Category: iodides-buliding-blocks This article mentions the following:

A visible-light-mediated oxidative iodination of electron-rich arenes was developed. 2.5 mol% of unsubstituted anthraquinone as photocatalyst were used in combination with elementary iodine, trifluoroacetic acid and oxygen as the terminal oxidant. The iodination proceeded upon irradiation in non- or weakly-electron donating solvents (DCM, DCE and benzene) wherein a spectral window in strongly colored iodine solutions was observed at around 400 nm. The method provided good to excellent yields (up to 98%) and showed excellent regioselectivity and good functional group tolerance (triple bonds, ketone, ester, amide). Moreover, the photo-iodination was also upscaled to a 5 mmol scale (1.1 g). Mechanistic investigations by intermediate trapping and competition experiments indicate a photocatalytic arene oxidation and the subsequent reaction with iodine as a likely mechanistic pathway. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Category: iodides-buliding-blocks).

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.Category: iodides-buliding-blocks

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

Gold(I)/Chiral Bronsted Acid Catalyzed Enantioselective Hydroamination-Hydroarylation of Alkynes: The Effect of a Remote Hydroxyl Group on the Reactivity and Enantioselectivity was written by Shinde, Valmik S.;Mane, Manoj V.;Vanka, Kumar;Mallick, Arijit;Patil, Nitin T.. And the article was included in Chemistry – A European Journal in 2015.Computed Properties of C6H3ClINO2 This article mentions the following:

The catalytic enantioselective hydroamination-hydroarylation of alkynes under the catalysis of (R₃P)AuMe/(S)-3,3′-bis(2,4,6-triisopropylphenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate ((S)-TRIP) is reported. The alkyne was reacted with a range of pyrrole-based aromatic amines to give pyrrole-embedded aza-heterocyclic scaffolds bearing a quaternary carbon center. The presence of a hydroxyl group in the alkyne tether turned out to be very crucial for obtaining products in high yields and enantioselectivities. The mechanism of enantioinduction was established by carefully performing exptl. and computational studies. In the experiment, the researchers used many compounds, for example, 4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1Computed Properties of C6H3ClINO2).

4-Chloro-2-iodo-1-nitrobenzene (cas: 160938-18-1) 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.Computed Properties of C6H3ClINO2

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

Product class 1: organometallic complexes of zinc was written by Knochel, P.. And the article was included in Science of Synthesis in 2004.Application of 10297-05-9 This article mentions the following:

Preparation of zinc organometallic complexes are reviewed including sections on aryl, hetaryl, allenyl, allyl, alkynyl, alkenyl, alkyl and carbenoid complexes and triorganozincates. Applications of the complexes for organic syntheses are briefly given. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Application of 10297-05-9).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. 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 10297-05-9

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

Biological activity of various halogenated derivatives of Ioxynil was written by Cooke, A. R.;Hart, R. D.;Achuff, N. E.. And the article was included in Proceedings of the Northeastern Weed Control Conference in 1965.Application of 2314-37-6 This article mentions the following:

Ioxynil (I) is effective for the control of broadleaf weeds and grasses in small grains. The 3,5-dibromo- and 3-bromo- acetates of I and 3,5-dibromo-4-hydroxybenzonitrile acetate are almost as effective. Less active are the 3,5-dichloro, 3-iodo-, 3-bromo-, 3-chloro-, 3,5-dinitro-, and 3-nitro-derivatives of I, p-hydroxybenzonitrile, 3,5-diiodo-4-hydroxybenzamide, 3,5-diiodo-4-hydroxybenzoic acid, 3,5-diiodo-4-hydroxybenzene-sulfonamide, 3,5-diiodo-4-hydroxybenzamide, 3,5-diiodo-4-hydroxybenzaldehyde and its oxime, 3-iodo-p-anisaldehyde, 3,5-dichloro-4-hydroxybenzaldehyde, 3,5-diiodo-4-hydroxyhydrocinnamic acid, p-cyanophenoxyacetic acid, 2,6-dibromo-4-cyanophenoxyacetic acid, 2-chloro-4-cyanophenoxyacetic acid, and 3,-4-diiodosalicylonitrile. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Application of 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. 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 of 2314-37-6

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

Molecular configuration of polynuclear aromatic compounds. IV. 6,6′-Dichlorodiphenic acid; its synthesis and resolution into optically active components was written by Christie, G. H.;James, C. W.;Kenner, James. And the article was included in Journal of the Chemical Society, Transactions in 1923.Recommanded Product: 123278-03-5 This article mentions the following:

2-Iodoaceto-m-toluidide is oxidized by KMnO₄ in boiling H₂O containing MgSO₄ to 2-iodo-3-acetylaminobenzoic acid, m. 199°. Hydrolysis with concentrated HCl gives the HCl salt of 2-iodo-3-aminobenzoic acid, m. 262-3°. 3-Chloro-2-iodobenzoic acid, m. 137-8°; Me ester, b₂₈ 182°; Et ester, b₁₅ 175°. The Me ester and Cu powder, heated 1 hr. at 230-40°, give 6,6′-dichlorodiphenic acid, m. 288°, as the Me ester, m. 156°. Et ester, m. 103-4°. Repeated fractional crystallization of the mixture of salts from 2 g. acid and 6 g. hydrated brucine gave 2.3 g. of brucine 1-6,6′-dichlorodiphenate, C₆₀H₆₀O₁₂N₄Cl₂.3H₂O, m. 235°; and is the less soluble of the 2 salts. [α]_D¹⁵ 1.97 (CHCl₃, c 1.23%). The d-salt, obtained in a yield of 1.35 g., m. 163° (decomposition), is the more soluble and has [α]_D¹⁵ -58.62° (CHCl₃, c 1.16%). This salt crystallines with 1.5 H₂O. d-6,6′-Dichlorodiphenic acid, m. 259°. A 0.69% solution of the Na salt showed [α]_D¹⁵ -20.18°. The l-acid m. 259°; a 1.01% aqueous solution of the Na salt showed [α]_D¹⁵ 21.43°. These results confirm the correctness of the assumption that the cause of the stereoisomerism of the various nitrodiphenic acids previously investigated is not to be sought in any peculiar property of the NO₂ group. In the experiment, the researchers used many compounds, for example, 3-Chloro-2-iodobenzoic acid (cas: 123278-03-5Recommanded Product: 123278-03-5).

3-Chloro-2-iodobenzoic acid (cas: 123278-03-5) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.Recommanded Product: 123278-03-5

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

Synthesis of Substituted Indole from 2-Aminobenzaldehyde through [1,2]-Aryl Shift was written by Levesque, Patrick;Fournier, Pierre-Andre. And the article was included in Journal of Organic Chemistry in 2010.Synthetic Route of C7H6INO2 This article mentions the following:

A mild, efficient, and simple method for the synthesis of 3-ethoxycarbonylindoles has been developed. Addition of Et diazoacetate (EDA) to 2-aminobenzaldehydes cleanly affords the indole core. E.g., addition of Et diazoacetate to 2-(benzylamino)-6-fluorobenzaldehyde (I) in presence of BF₃.OEt₂ gave 85% Et 1-benzyl-4-fluoroindole-3-carboxylate (II). As opposed to other common approaches for the synthesis of indole, this method displays both excellent functional group tolerance and perfect regiochem. control. This allowed the synthesis of a variety of useful indole building blocks from 2-aminobenzaldehydes derived from readily available anthranilic acids. In the experiment, the researchers used many compounds, for example, 2-Amino-4-iodobenzoic acid (cas: 20776-54-9Synthetic Route of C7H6INO2).

2-Amino-4-iodobenzoic acid (cas: 20776-54-9) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. 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.Synthetic Route of C7H6INO2

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

Synthesis, biological evaluation and molecular modeling of a novel series of 7-azaindole based tri-heterocyclic compounds as potent CDK2/Cyclin E inhibitors was written by Baltus, Christine B.;Jorda, Radek;Marot, Christophe;Berka, Karel;Bazgier, Vaclav;Krystof, Vladimir;Prie, Gildas;Viaud-Massuard, Marie-Claude. And the article was included in European Journal of Medicinal Chemistry in 2016.Electric Literature of C7H5IN2 This article mentions the following:

From four mols., inspired by the structural features of fascaplysin, with an interesting potential to inhibit cyclin-dependent kinases (CDKs), we designed a new series of tri-heterocyclic derivatives based on 1H-pyrrolo[2,3-b]pyridine (7-azaindole) and triazole heterocycles. Using a Huisgen type [3 + 2] cycloaddition as the convergent key step, 24 derivatives were synthesized and their biol. activities were evaluated. Comparative mol. field anal. (CoMFA), based on three-dimensional quant. structure-activity relationship (3D-QSAR) studies, was conducted on a series of 30 compounds from the literature with high to low known inhibitory activity towards CDK2/cyclin E and was validated by a test set of 5 compounds giving satisfactory predictive r² value of 0.92. Remarkably, it also gave a good prediction of pIC₅₀ for our tri-heterocyclic series which reinforce the validation of this model for the pIC₅₀ prediction of external set compounds The most promising compound, I, showed a micro-molar range inhibitory activity against CDK2/cyclin E and also an antiproliferative and proapoptotic activity against a panel of cancer cell lines. In the experiment, the researchers used many compounds, for example, 2-Iodo-1H-pyrrolo[2,3-b]pyridine (cas: 1227270-32-7Electric Literature of C7H5IN2).

2-Iodo-1H-pyrrolo[2,3-b]pyridine (cas: 1227270-32-7) 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.Electric Literature of C7H5IN2

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

Transition-metal-free decarboxylative iodination: New routes for decarboxylative oxidative cross-couplings was written by Perry, Gregory J. P.;Quibell, Jacob M.;Panigrahi, Adyasha;Larrosa, Igor. And the article was included in Journal of the American Chemical Society in 2017.Product Details of 36748-88-6 This article mentions the following:

Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional mols., and efficient methods for their synthesis from chem. feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I₂. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I₂ as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Product Details of 36748-88-6).

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. 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 36748-88-6

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