Month: February 2023

Two bicyclic dinuclear complexes generated from 3,3′-[1,3,4-thiadiazole-2,5-diyldi(thiomethylene)]dibenzoic acid (L) and dimethylformamide (DMF): [Cu(L)(DMF)]₂ and [Zn(L)(DMF)]₂ was written by Wang, Ping;Ma, Jian-Ping;Li, Xiao-Yan;Huang, Ru-Qi;Dong, Yu-Bin. And the article was included in Acta Crystallographica, Section C: Crystal Structure Communications in 2009.Category: bromides-buliding-blocks This article mentions the following:

A new 1,3,4-thiadiazole bridging ligand, 3,3′-[1,3,4-thiadiazole-2,5-diyldi(thiomethylene)]dibenzoic acid (L), was used to create the novel isomorphous complexes bis{μ-3,3′-[1,3,4-thiadiazole-2,5-diyldi(thiomethylene)]dibenzoato}bis[(DMF)copper(II)], [Cu₂(C₁₈H₁₂N₂O₄S₃)₂(C₃H₇NO)₂], (I), and bis{μ-3,3′-[1,3,4-thiadiazole-2,5-diyldi(thiomethylene)]dibenzoato}bis[(DMF)zinc(II)], [Zn₂(C₁₈H₁₂N₂O₄S₃)₂(C₃H₇NO)₂], (II). Crystallog. data are given. Both exist as centrosym. bicyclic dimers constructed through the syn-syn bidentate bridging mode of the carboxylate groups. The two rings share a metal-metal bond and each of the metal atoms possesses a square-pyramidal geometry capped by the DMF mol. The 1,3,4-thiadiazole rings play a critical role in the formation of a π-π stacking system that expands the dimensionality of the structure from zero to one. The TGA of (I) indicates decomposition of the coordinated ligands on heating. Compared with the fluorescence of L in the solid state, the fluorescence intensity of (II) is relatively enhanced with a slight red shift, while that of (I) is quenched. In the experiment, the researchers used many compounds, for example, 3-(Bromomethyl)benzoic acid (cas: 6515-58-8Category: bromides-buliding-blocks).

3-(Bromomethyl)benzoic acid (cas: 6515-58-8) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and Radiosynthesis of Prospective 2-Nitroimidazole Hypoxia PET Tracers via Thiazolidine Ligation with 5-Fluorodeoxyribose (FDR) was written by Musolino, M.;Dall’Angelo, S.;Zanda, M.. And the article was included in SynOpen in 2017.Quality Control of N-(5-Bromopentyl)phthalimide This article mentions the following:

The first prospective fluorinated PET tracers for imaging hypoxia obtained via thiazolidine-ligation are reported. Three 1,2-thiol-amine linkers were combined with four different 2-nitroimidazole spacers via amide or urea bond formation. The resulting compounds, e.g., I were submitted to thiazolidine-ring-forming ligation reaction with the fluorinated carbohydrate L-5-fluoro-5-deoxy-ribose (FDR), affording the desired candidate PET tracers, e.g., II in variable yields. The same ligation reactions performed on L-ribose – a byproduct of [18F]FDR radiosynthesis – under conditions mimicking a radiochem. production and showed that the fluorinated adducts can be efficiently purified and isolated by HPLC. Finally, one of the prospective hypoxia tracers was successfully produced in radiolabeled form in 29.2% radiochem. yield from [18F]FDR. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Quality Control of N-(5-Bromopentyl)phthalimide).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Quality Control of N-(5-Bromopentyl)phthalimide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of unsymmetrical dihydro triazine-2,4-diones by the N-N bond fragmentation of urazoles followed by intramolecular cyclization was written by Panga, Subhaskar R.;Hall, Roger G.;Samant, Rashmi V.;Montgomery, Mark;Shyadligeri, Ashok S.. And the article was included in Tetrahedron Letters in 2022.Application In Synthesis of 1-Bromopyrrolidine-2,5-dione This article mentions the following:

A new synthesis of unsym. dihydro triazine-2,4-diones I (R¹ = Ph, 3-ClC₆H₄, 4-MeOC₆H₄, 1-phenyl-3-trifluoromethylpyrazol-5-yl, etc., R² = H, R³ = Me; R¹ = 4-ClC₆H₄, R² = H, Me, R³ = Me, Et, i-Pr) has been accomplished through the strategy of a base-induced fragmentation of urazole derivatives II followed by an intramol. cyclization. Treating substituted urazole derivativesII with LDA resulted in fragmentation of the N-N bond generating an imine, which was trapped in an intramol. fashion to give products I in good to excellent yields. Features of this transformation include atom economy and a broad tolerance of aryl substituents. Where differentially substituted urazole derivatives were employed, only one dihydrotriazine-2,4-dione isomer was obtained. The transformation of the formed dihydrotriazine-2,4-diones into triazine-2,4-diones and triazine-2,4,6-triones has been demonstrated, enlarging the scope of this approach. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Application In Synthesis of 1-Bromopyrrolidine-2,5-dione).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Application In Synthesis of 1-Bromopyrrolidine-2,5-dione

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Improved Flavodoxin Inhibitors with Potential Therapeutic Effects against Helicobacter pylori Infection was written by Galano, Juan J.;Alias, Miriam;Perez, Reyes;Velazquez-Campoy, Adrian;Hoffman, Paul S.;Sancho, Javier. And the article was included in Journal of Medicinal Chemistry in 2013.Application In Synthesis of 1-(3-Bromopropyl)-4-methoxybenzene This article mentions the following:

A variety of electron-deficient chromenes and styrenes and nitrobenzooxadiazolyl thioethers and other compounds were tested (and in some cases prepared) as selective inhibitors of flavodoxin in Helicobacter pylori for potential use in the treatment of gastric ulcer and prevention of stomach cancer with fewer side effects and reduced susceptibilities to drug resistance; their inhibition of flavodoxin and of Helicobacter pylori and their cytotoxicities were determined For example, (E)-ArCH:CHNO₂ (Ar = 2-F-5-F₃CC₆H₃, 4-Cl-2,6-F₂C₆H₂) inhibited H. pylori with IC₅₀ values of 0.53 μM and therapeutic indexes of 38 and 15, resp. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Application In Synthesis of 1-(3-Bromopropyl)-4-methoxybenzene).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Application In Synthesis of 1-(3-Bromopropyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

A Direct and Efficient Total Synthesis of the Tubulin-Binding Agents Ceratamine A and B; Use of IBX for a Remarkable Heterocycle Dehydrogenation was written by Coleman, Robert S.;Campbell, Erica L.;Carper, Daniel J.. And the article was included in Organic Letters in 2009.HPLC of Formula: 108940-96-1 This article mentions the following:

The total synthesis of the tubulin-binding agents (no biol. testing data presented) ceratamines A and B I (R = Me, H, resp., R¹ = Me) was reported, along with des-Me analogs I (R = Me, H, R¹ = H), via a synthetic route that is high-yielding and operationally efficient. The synthetic route involved a Beckmann rearrangement to form an azepine ring precursor, a Knoevenagel condensation to install the benzylic side chain, and an effective imidazole annulation onto an α-aminoketone precursor with a protected S-methylisothiourea. Final dehydrogenation proved remarkably facile using IBX. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1HPLC of Formula: 108940-96-1).

3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.HPLC of Formula: 108940-96-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Phosphorescence of polynuclear aromatic hydrocarbons in heptakis(6-bromo-6-deoxy-β-cylcodextrin) was written by Femia, R. A.;Love, L. J. Cline. And the article was included in Journal of Physical Chemistry in 1985.Name: Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin This article mentions the following:

Room-temperature phosphorescence spectra and excited-state lifetimes are reported for several polynuclear aromatic hydrocarbons included within the cavity of heptakis(6-bromo-6-deoxy-β-cyclodextrin) (Br-β-CD) (synthesized by replacing β-CD’s primary hydroxyls with Br). Appreciable phosphorescence only occurs when the lumiphor is shielded from quenchers by the cyclodextrin torus and are within the realm of influence of heavy atoms. By locking the heavy atom into a fixed position on the cyclodextrin mol., the observed phosphorescence and dynamic interactions depend primarily on the entrance and exit rate constants of the lumiphor from the cyclodextrin, simplifying the kinetic scheme and data interpretation. A solvent mixture of DMF and water was employed due to the extreme water insolubility of heptakis(6-bromo-6-deoxy-β-cyclodextrin), and to assess the degree of bulk solvent hydrophobicity on the inclusion process. This latter effect was monitored by differences in phenanthrene’s Br-β-CD spectral profile relative to that in aqueous unbrominated β-CD/1,2-dibromoethane and fluorescence peak ratio variations as a function of the DMF/water ratio. Luminescence lifetime values provided indirect information on the relative exit-to-entrance rate constant ratios. The optimum DMF/water ratio for production of maximum phosphorescence intensity was 4/1, and the optimum concentration of brominated β-cyclodextrin in the 4/1 DMF/water solvent was 0.01 M. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Name: Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Name: Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Impact of Entropic Effects in the Classical Resolution of a 2-Arylpyrrolidine was written by Barnes, David M.;Barkalow, Jufang;Chen, Yong;Gupta, Ashok;Haight, Anthony R.;Hengeveld, John E.;Kerdesky, Francis A. J.;Kotecki, Brian J.;Macri, Bryan;Pal, Agnes. And the article was included in Organic Process Research & Development in 2009.Product Details of 179232-29-2 This article mentions the following:

The impact of entropic effects on the classical salt resolution of a 2-arylpyrrolidine I·D-tartrate is described. The crystallization of a racemic mixture of the base with tartaric acid led to a salt in which the undesired enantiomer is incorporated into the crystal lattice as a solid solution The product enantiomer ratio was later determined to be at the thermodn. well when the racemate is crystallized In order to circumvent this effect, an efficient two-crystallization resolution was developed. The bulk of the undesired enantiomer is removed in the first crystallization so that the second crystallization can result in material of acceptable optical purity. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2Product Details of 179232-29-2).

Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Product Details of 179232-29-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Bench-Stable Stock Solutions of Silicon Grignard Reagents: Application to Iron- and Cobalt-Catalyzed Radical C(sp³)-Si Cross-Coupling Reactions was written by Xue, Weichao;Shishido, Ryosuke;Oestreich, Martin. And the article was included in Angewandte Chemie, International Edition in 2018.SDS of cas: 14425-64-0 This article mentions the following:

A robust method for the preparation of silicon-based magnesium reagents is reported. The MgBr₂ used in the lithium-to-magnesium transmetalation step is generated in situ from 1,2-dibromoethane and elemental magnesium in hot THF. No precipitation of MgBr₂ occurs in the heat, and transmetalation at elevated temperature leads to homogeneous stock solutions of the silicon Grignard reagents that are stable and storable in the fridge. This method avoids the preparation of silicon pronucleophiles such as Si-Si and Si-B reagents. The new Grignard reagents were applied to unprecedented iron- and cobalt-catalyzed cross-coupling reactions of unactivated alkyl bromides. The functional-group tolerance of these magnesium reagents is excellent. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0SDS of cas: 14425-64-0).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.SDS of cas: 14425-64-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

MeOTf-Catalyzed Intramolecular Acyl-Cyclization of Aryl Isocyanates: Efficient Access to Phenanthridin-6(5H)-one and 3,4-Dihydroisoquinolin-1(2H)-one Derivatives was written by Zou, Song;Zhang, Zeyu;Chen, Chao;Xi, Chanjuan. And the article was included in Asian Journal of Organic Chemistry in 2021.Formula: C9H11BrO This article mentions the following:

MeOTf-catalyzed intramol. acyl-cyclization of aryl isocyanates has been realized to provide (NH)-phenanthridinones and lactams under metal-free conditions. A variety of functional groups are tolerated in their scaffolds with good to excellent yields. The reaction could be carried to gram scale and a range of natural alkaloids, such as crinasiadine, benzophenidine alkaloid (ZYH005), N-methylcrinasiadine, and trisphaeridine could be synthesized directly or in short steps with high yields. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Formula: C9H11BrO).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Formula: C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Intramolecular Pd-Catalyzed Reductive Amination of Enolizable sp³-C-H Bonds was written by Ford, Russell L.;Alt, Isabel;Jana, Navendu;Driver, Tom G.. And the article was included in Organic Letters in 2019.Computed Properties of C7H5BrFNO2 This article mentions the following:

A palladium-catalyzed reductive cyclization of nitroarenes has been designed to construct sp³-C-NHAr bonds from sp³-C-H bonds by using an enolizable nucleophile to intercept a nitrosoarene intermediate. Exposure of ortho-substituted nitroarenes to 5 mol % of Pd(OAc)₂ and 10 mol % of phenanthroline under 2 atm of CO constructs partially saturated 5-, 6-, or 7-membered N-heterocycles I (R¹ = H, Cl, Me, etc.; R² = H, F, Me, etc.; R³ = H, Me) using α-pyridyl carboxylates, malonates, 1,3-dimethylbarbituric acid, 1,3-diones, or difurans as the nucleophile. In the experiment, the researchers used many compounds, for example, 1-(Bromomethyl)-4-fluoro-2-nitrobenzene (cas: 76437-44-0Computed Properties of C7H5BrFNO2).

1-(Bromomethyl)-4-fluoro-2-nitrobenzene (cas: 76437-44-0) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Computed Properties of C7H5BrFNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary