Month: January 2023

Regioselective monobromination of phenols with KBr and ZnAl-BrO₃^–-layered double hydroxides was written by Wang, Ligeng;Feng, Chun;Zhang, Yan;Hu, Jun. And the article was included in Molecules in 2020.Category: iodides-buliding-blocks This article mentions the following:

The regioselective mono-bromination of phenols was successfully developed with KBr and ZnAl-BrO₃^–-layered double hydroxides (abbreviated as ZnAl-BrO₃^–-LDHs) as brominating reagents. The para site was much favorable and the ortho site takes the priority if para site was occupied. This reaction featured with excellent regioselectivity, cheap brominating reagents, mild reaction condition, high atom economy, broad substrate scope, and provided an efficient method to synthesize bromophenols. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Category: iodides-buliding-blocks).

4-Bromo-2-iodophenol (cas: 207115-22-8) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. 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.Category: iodides-buliding-blocks

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

Catalytic Enantioselective Synthesis of Difluorinated Alkyl Bromides was written by Levin, Mark D.;Ovian, John M.;Read, Jacquelyne A.;Sigman, Matthew S.;Jacobsen, Eric N.. And the article was included in Journal of the American Chemical Society in 2020.COA of Formula: C8H7IO4 This article mentions the following:

An iodoarene-catalyzed (R,R)/(S,S)I (R = Ph, 3-chlorophenyl, 3,4,5-trifluorophenyl, 2-Me Ph, etc.; R¹ = Me, Bn) enantioselective synthesis of β,β-difluoroalkyl bromide (R)-R²C(F₂)CH(Br)R³ (R² = 3-nitropenyl, 4-bromophenyl, 4-trifluoromethylphenyl, 1-methyl-1H-pyrazol-4-yl, etc.; R³ = Me, Et, nBu, iPr, etc.) building blocks was reported. The transformation involves an oxidative rearrangement of α-bromostyrenes R²C(Br)=CHR³, utilizing HF-pyridine as the fluoride source and m-CPBA as the stoichiometric oxidant. A catalyst decomposition pathway was identified, which, in tandem with catalyst structure-activity relationship studies, facilitated the development of an improved catalyst providing higher enantioselectivity with lower catalyst loadings. The versatility of the difluoroalkyl bromide products was demonstrated via highly enantiospecific substitution reactions with suitably reactive nucleophiles. The origins of enantioselectivity were investigated using computed interaction energies of simplified catalyst and substrate structures, providing evidence for both CH-π and π-π transition state interactions as critical features. In the experiment, the researchers used many compounds, for example, Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7COA of Formula: C8H7IO4).

Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7) 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. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.COA of Formula: C8H7IO4

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

An N-Acyliminium Cyclization Approach to a Total Synthesis of (+)-Cylindricine C was written by Liu, Jia;Swidorski, Jacob J.;Peters, Scott D.;Hsung, Richard P.. And the article was included in Journal of Organic Chemistry in 2005.Related Products of 10297-05-9 This article mentions the following:

Details of problems and solutions encountered during the development of an enantioselective total synthesis of (+)-cylindricine C (I) are described here. The total synthesis itself was accomplished in 8 steps, featuring an N-acyliminium cyclization strategy, the seldom-used Wharton rearrangement, and a key epimerization at C5. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Related Products of 10297-05-9).

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. 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.Related Products of 10297-05-9

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

Enantioselective, Catalytic Vicinal Difluorination of Alkenes was written by Scheidt, Felix;Schaefer, Michael;Sarie, Jerome C.;Daniliuc, Constantin G.;Molloy, John J.;Gilmour, Ryan. And the article was included in Angewandte Chemie, International Edition in 2018.Safety of Methyl 3,5-dihydroxy-4-iodobenzoate This article mentions the following:

An efficient method was developed for the synthesis of 1,2-difluoroethyl arenes ArCH(F)CH₂F [Ar = 3-CNC₆H₄, 4-O₂NC₆H₄, 2-SO₂MeC₆H₄, etc.] via enantioselective I^I/I^III catalytic vicinal difluorination of terminal alkenes using novel C₂-sym. resorcinol derivative Catalyst turnover via in situ generation of an ArI^IIIF₂ species was enabled by Selectfluor oxidation and addition of an inexpensive HF-amine complex. The HF:amine ratio employed in this process provided a handle for regioselective orthogonality as a function of Bronsted acidity. Selectivity reversal from the 1,1-difluorination pathway (geminal) to the desired 1,2-difluorination (vicinal) was disclosed (>20:1 in both directions). An achiral variant of the reaction was also presented using p-iodotoluene (up to >95 % yield). In the experiment, the researchers used many compounds, for example, Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7Safety of Methyl 3,5-dihydroxy-4-iodobenzoate).

Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7) 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.Safety of Methyl 3,5-dihydroxy-4-iodobenzoate

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

Synthesis of 5-Arylpyrrole-2-carboxylic Acids as Key Intermediates for NBD Series HIV-1 Entry Inhibitors was written by Belov, Dmitry S.;Ivanov, Vladimir N.;Curreli, Francesca;Kurkin, Alexander V.;Altieri, Andrea;Debnath, Asim K.. And the article was included in Synthesis in 2017.Computed Properties of C8H9IO2 This article mentions the following:

5-Arylpyrrole-2-carboxylic acids are important key intermediates in the synthesis of HIV-1 entry inhibitors (such as NBD-11021 and NBD-14010). Herein, a general method for the synthesis of some 5-arylpyrrole-2-carboxylic acids, e.g., I, in three steps starting from pyrrole is presented. By this method, the compounds could be prepared on gram scale and without chromatog. purification 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. Organic iodides are widely used in organic synthesis. Halogenation of aromatic hydrocarbons is a very important reaction via an electrophilic aromatic substitution. 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.Computed Properties of C8H9IO2

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

Construction of peptide macrocycles via palladium-catalyzed multiple S-arylation: An effective strategy to expand the structural diversity of cross-linkers was written by Chu, Xin;Shen, Linhua;Li, Bo;Yang, Peng;Du, Chengzhuo;Wang, Xiaoye;He, Gang;Messaoudi, Samir;Chen, Gong. And the article was included in Organic Letters in 2021.Quality Control of Bis(2-iodothiophen-3-yl)methanone This article mentions the following:

A simple and versatile method for macrocyclizing unprotected native peptides with a wide range of easily accessible diiodo and triiodoarene reagents via the palladium-catalyzed multiple S-arylation of cysteine residues is developed. Iodoarenes with different arene and heteroarene cores can be incorporated into peptide macrocycles of varied ring sizes and amino acid compositions with high efficiency and selectivity under mild conditions. In the experiment, the researchers used many compounds, for example, Bis(2-iodothiophen-3-yl)methanone (cas: 474416-61-0Quality Control of Bis(2-iodothiophen-3-yl)methanone).

Bis(2-iodothiophen-3-yl)methanone (cas: 474416-61-0) 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.Quality Control of Bis(2-iodothiophen-3-yl)methanone

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

A Practical Chiral Bicyclic Thioglycolate Lactam Auxiliary for Stereoselective Quaternary Carbon Formation was written by Arpin, Azelie;Manthorpe, Jeffrey M.;Gleason, James L.. And the article was included in Organic Letters in 2006.Reference of 10297-05-9 This article mentions the following:

Chiral bicyclic thioglycolate lactams may be prepared in three steps from inexpensive com. materials. The resulting lactams may be alkylated three times, twice using basic enolization and once using reductive enolization, to form α-quaternary carboxylic acid derivatives in high yield and with high diastereoselectivity. The alkylation products may be cleaved under either acidic or reductive conditions to furnish either carboxylic acids or primary alcs., resp. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Reference of 10297-05-9).

1-Chloro-4-iodobutane (cas: 10297-05-9) 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. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Reference of 10297-05-9

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

Coupling of N-heterocycle-fused enyne aldehydes with γ,δ-unsaturated Fischer carbene complexes was written by Zhang, Jianwei;Zhang, Yanshi;Schnatter, Wayne F. K.;Herndon, James W.. And the article was included in Organometallics in 2006.HPLC of Formula: 15813-09-9 This article mentions the following:

The coupling of γ,δ-unsaturated Fischer carbene complexes, e.g. H₂C:CHCH₂CH₂C(OMe):Cr(CO)₅ with enyne aldehyde derivatives fused to indole, imidazole, and pyrazole ring systems, e.g. I (R¹ = Me₃Si, n-Bu; R² = PhCH₂, PhCHMe, ribofuranosyl; R³ = H, Me₃C, Ph), has been examined The reaction leads to heterocycles fused to the hydronaphthalene ring system, e.g. II, in a single step. The products of the reaction feature heterocycles fused either to benzene rings or to a cyclohexane ring. The product distribution correlates with the electronic richness of the heterocyclic ring. A moderate degree of diastereoselectivity was observed using heterocycles featuring chiral nitrogen substituents. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9HPLC of Formula: 15813-09-9).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. 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: 15813-09-9

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

Ynamide Click chemistry in development of triazole VEGFR2 TK modulators was written by Vojtickova, Margareta;Dobias, Juraj;Hanquet, Gilles;Addova, Gabriela;Cetin-Atalay, Rengul;Yildirim, Deniz Cansen;Bohac, Andrej. And the article was included in European Journal of Medicinal Chemistry in 2015.Recommanded Product: 4-Bromo-2-iodophenol This article mentions the following:

Structure novelty, chem. stability and synthetic feasibility attracted us to design 1,2,3-triazole compounds as potential inhibitors of VEGFR2 tyrosine kinase. Novel triazoles I [R¹ = OH, R² = pyrrrol-3-yl; R¹ = H, OH, R² = 2-pyridinyl; R¹ = H, OH, R² = pyridin-3-yl; R¹ = 1-naphthyl, R² = NHC(:O)NH₂] and II were proposed by oxazole (III from PDB: 1Y6A)/1,2,3-triazole isosteric replacement, mol. modeling and docking. In order to enable synthesis of I and II we developed a methodol. for preparation of ynamide IV [EWG = CO₂Me, Boc, Ts, Ph]. Compound IV was used for all Click chem. reactions leading to triazoles I [R¹ = OH, R² = 3-pyrrolyl, R¹ = 1-naphthyl, R² = NHC(:O)NH₂; R¹ = OH, R² = 2-pyridinyl] and I [R¹ = H, R² = 2-pyridinyl, 3-pyridinyl] . Among the obtained products, I [R¹ = OH, R² = pyrrol-3-yl, pyridin-2-yl; R¹ = H, R² = pyridin-2-yl] specifically bind VEGFR2 TK and modulate its activity by concentration dependent manner. Moreover predicted binding poses of II and II in VEGFR2 TK were similar to the one known for the oxazole inhibitor III (PDB: 1Y6A). Unfortunately the VEGFR2 inhibition by triazoles, e.g., I [R¹ = H, OH, R² = pyridin-2-yl], is lower than that determined for their oxazole bioisosters III and V, resp. Different electronic properties of 1,2,3-triazole/oxazole heterocyclic rings were proposed to be the main reason for the diminished affinity of I [R¹ = OH, R² = pyrrrol-3-yl; R¹ = OH, R² = 2-pyridinyl; R¹ = H R² = pyridin-3-yl; R¹ = 1-naphthyl, R² = NHC(:O)NH₂] to an oxazole III inhibitor binding site in VEGFR2 TK (PDB: 1Y6A or 1Y6B). Moreover I [R¹ = OH, R² = pyrrrol-3-yl; R¹ = H, OH, R² = 2-pyridinyl; R¹ = H R² = pyridin-3-yl; R¹ = 1-naphthyl, R² = NHC(:O)NH₂] were screened on cytotoxic activity against two human hepatocellular carcinoma cell lines. Selective cytotoxic activity of I [R¹ = 1-naphthyl, R² = NHC(:O)NH₂] against aggressive Mahlavu cells has been discovered indicating possible affinity of I [R¹ = 1-naphthyl, R² = NHC(:O)NH₂] to Mahlavu constitutionally active PI3K/Akt pathway. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Recommanded Product: 4-Bromo-2-iodophenol).

4-Bromo-2-iodophenol (cas: 207115-22-8) 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.Recommanded Product: 4-Bromo-2-iodophenol

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

Efficient Copper-Catalyzed Trifluoromethylation of Aromatic and Heteroaromatic Iodides: The Beneficial Anchoring Effect of Borates was written by Gonda, Zsombor;Kovacs, Szabolcs;Weber, Csaba;Gati, Tamas;Meszaros, Attila;Kotschy, Andras;Novak, Zoltan. And the article was included in Organic Letters in 2014.Synthetic Route of C11H14INO This article mentions the following:

Efficient copper-catalyzed trifluoromethylation of aromatic iodides was achieved with TMSCF₃ in the presence of tri-Me borate. The Lewis acid was used to anchor the in situ generated trifluoromethyl anion and suppress its rapid decomposition Broad applicability of the new trifluoromethylating reaction was demonstrated in the functionalization of different aromatic and heteroaromatic iodides. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Synthetic Route of C11H14INO).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) 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.Synthetic Route of C11H14INO

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