Tag: 200-300

[Multicomponent Synthesis of 4-Aminophthalazin-1(2H)-ones by Palladium-Catalyzed Isocyanide Insertion was written by Vlaar, Tjoestil;Mampuys, Pieter;Helliwell, Madeleine;Maes, Bert U. W.;Orru, Romano V. A.;Ruijter, Eelco. And the article was included in Journal of Organic Chemistry in 2013.Related Products of 653-92-9 This article mentions the following:

4-Aminophthalazin-1(2H)-ones (APOs) are underexplored heterocyclic compounds with promising and diverse biol. activities. The classical synthesis of these compounds is tedious and does not allow the regioselective introduction of substituents. Here, we present our full studies on the Pd-catalyzed cross-coupling of substituted o-(pseudo)halobenzoates and hydrazines with isocyanide insertion allowing straightforward access to diversely substituted APOs. E.g., in presence of Pd(OAc)₂ and Xantphos in DMSO, reaction of benzoate ester (I), tert-Bu isocyanide, and hydrazine hydrate gave 89% 4-aminophthalazin-1(2H)-one derivative (II). We illustrate the advantages of this method compared to other approaches and describe solutions for the limitations we encountered. In addition, we have developed efficient diversifications of this heterocyclic scaffold that allow access to more diverse APOs as well as novel heterocyclic scaffolds. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9Related Products of 653-92-9).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Related Products of 653-92-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of N-Methylpyrrole and N-Methylimidazole Amino Acids Suitable for Solid-Phase Synthesis was written by Jaramillo, David;Liu, Qi;Aldrich-Wright, Janice;Tor, Yitzhak. And the article was included in Journal of Organic Chemistry in 2004.Name: Methyl 4-bromo-1-methyl-1H-pyrrole-2-carboxylate This article mentions the following:

New and higher yielding synthetic routes to Boc-protected N-methylpyrrole and N-methylimidazole amino acids are introduced to circumvent difficulties associated with established schemes. Key step in the synthesis of pyrrole amino acid I was copper-mediated cross-coupling reaction of Me 4-bromo-N-methyl-2-pyrrolecarboxylate with tert-Bu carbamate to directly install a carbamate-protected amino group. Key step in the synthesis of imidazole amino acid II was nitration of 1-methyl-2-(trichloroacetyl)imidazole followed by a one-pot reduction/Boc protection of the amine. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-1-methyl-1H-pyrrole-2-carboxylate (cas: 1196-90-3Name: Methyl 4-bromo-1-methyl-1H-pyrrole-2-carboxylate).

Methyl 4-bromo-1-methyl-1H-pyrrole-2-carboxylate (cas: 1196-90-3) 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. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Name: Methyl 4-bromo-1-methyl-1H-pyrrole-2-carboxylate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Optically active bithienyls. II. Synthesis and resolution of2,2′-dicarboxy-4,4′-dibromo-5,5′-dimethyl-3,3′-bithienyl was written by Gronowitz, Salo;Frostling, Harold. And the article was included in Acta Chemica Scandinavica in 1962.Application of 29421-99-6 This article mentions the following:

Atropisomerism has been demonstrated for the first time in the 3,3′-bithienyl series. 4-Bromo-2-thiophenealdehyde (202 g.), 200 ml. 99% N₂H₄.H₂O, and 500 ml. ethylene glycol was heated at 130-140° and H₂O and excess hydrazine distilled The solution was cooled, 200 g. KOH added, and the mixture heated to 90° until a vigorous reaction occurred, then heated an addnl. 15 min., steam distilled, and extracted with Et₂O to yield 167 g. 4-bromo-2-methylthiophene (I), b₁₁ 61-2°, n²⁰_D 1.5725. To 160 g. I in 150 ml. anhydrous Et₂O was added 1300 ml. 0.9N BuLi at -70°. After 5 min. 134 g. anhydrous CuCl₂ was added and the mixture stirred 3 hrs. at -70°. After 3 hrs. at room temperature the product was worked up to give 19 g. 5,5′-dimethyl-3,3′-bithienyl (II), m. 135-6° (ligroine). BuLi (500 ml., 0.9N) was added to 18.5 g. II in 300 ml. dry Et₂O and the mixture refluxed for 2 hrs., poured on solid CO₂ in Et₂O, and hydrolyzed at -10° with H₂O. The Et₂O phase yielded 12 g. 2,2′-dicarboxy-5,5′-dimethyl-3,3’bithienyl (III), m. 254-7° (decomposition) (HOAc). An excess of Br was poured on 7.0 g. III. The Br was evaporated, and the residue heated with 200 ml. Na₂CO₃, filtered, and acidified with 2N HCl. The crude acid was recrystallized from HOAc to yield 8.5 g. 2,2′-dicarboxy-4,4′-dibromo-5,5′-dimethyl-3,3′-bithienyl (IV), m. 311-13° (decomposition); di-Me ester m. 15-46° (EtOH). 4-Bromo-5-methyl-2-thiophenecarboxylic acid was prepared by bromination of 5-methyl-2-thiophenecarboxylic acid in HOAc, m. 197-8° (aqueous EtOH). Fractional crystallization of the cinchonine salt of IV from aqueous EtOH resulted in a separation of the optical antipodes (+)-IV, m. 302-5° (decomposition),[α]²⁵_D 43° (aqueous EtOH), and (-)-IV, m. 301-4° (decomposition), [α]²⁵_D -43° (aqueous EtOH). The rotations of (+)-IV in other solvents were as follows (solvent and [α]²⁵_D given): acetone, 43°; Me₂SO, 53°, EtOH, 55°; CHCl₃, -57.5°; 0.1N NaOH, -1.90°. In the experiment, the researchers used many compounds, for example, 4-Bromo-5-methylthiophene-2-carboxylic acid (cas: 29421-99-6Application of 29421-99-6).

4-Bromo-5-methylthiophene-2-carboxylic acid (cas: 29421-99-6) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon–bromine bond is electrophilic in nature. 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 of 29421-99-6

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Radiosynthesis and evaluation of novel ^99mTc(CO)₃-labelled thymidine dithiocarbamate derivatives for tumor imaging with SPECT was written by Duan, Xiaojiang;Ruan, Qing;Gan, Qianqian;Song, Xiaoqing;Fang, Si’an;Zhang, Xuran;Zhang, Junbo. And the article was included in Journal of Organometallic Chemistry in 2018.Computed Properties of C13H14BrNO2 This article mentions the following:

A series of novel thymidine dithiocarbamate derivatives (DTC-TdR) were successfully synthesized and then radiolabeled using [^99mTc(CO)₃]⁺ core with high yields. The chem. characterizations of ^99mTc(CO)₃-labeled dithiocarbamate derivatives have been carried out by preparing their corresponding rhenium complexes. The radiotracers were stable in vitro, and the partition coefficient results indicated that they were lipophilic. The cell uptake studies showed the uptakes of these ^99mTc(CO)₃-labeled thymidine derivatives were mediated by nucleoside transporters. Biodistribution of the complexes in mice bearing tumor showed that they had high tumor uptake and good tumor/muscle ratio. A clear SPECT imaging of the tumor location was obtained in mice bearing S180 tumor with one of radiotracers, suggesting they would be potential tumor imaging agents. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Computed Properties of C13H14BrNO2).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Computed Properties of C13H14BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Nickel^II-catalyzed asymmetric photoenolization/Mannich reaction of (2-alkylphenyl) ketones was written by Yang, Liangkun;Li, Wang-Yuren;Hou, Liuzhen;Zhan, Tangyu;Cao, Weidi;Liu, Xiaohua;Feng, Xiaoming. And the article was included in Chemical Science in 2022.HPLC of Formula: 85118-24-7 This article mentions the following:

A diastereo- and enantioselective photoenolization/Mannich (PEM) reaction of ortho-alkyl aromatic ketones with benzosulfonimides were established by utilizing a chiral N,N’-dioxide/Ni(OTf)₂ complex as the Lewis acid catalyst. It afforded a series of benzosulfonamides and the corresponding ring-closure products and a reversal of diastereoselectivity were observed through epimerization of the benzosulfonamide products under continuous irradiation On the basis of the control experiments, the role of the additive LiNTf₂ in achieving high stereoselectivity were elucidated. This PEM reaction were proposed to undergo a direct nucleophilic addition mechanism rather than a hetero-Diels-Alder/ring-opening sequence. A possible transition state model with a photoenolization process were proposed to explain the origin of the high level of stereoinduction. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7HPLC of Formula: 85118-24-7).

2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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.HPLC of Formula: 85118-24-7

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Preparation of 3-benzyloxy-2-pyridinone functional linkers: tools for the synthesis of 3,2-hydroxypyridinone (HOPO) and HOPO/hydroxamic acid chelators was written by Gibson, Sarah;Fernando, Rasika;Jacobs, Hollie K.;Gopalan, Aravamudan S.. And the article was included in Tetrahedron in 2015.COA of Formula: C13H14BrNO2 This article mentions the following:

In contrast to 2,3-dihydroxypyridine, the 3-benzyloxy protected derivative, 2 (I), undergoes facile alkylation at ambient temperatures with a variety of functionalized alkyl halides in good yields. This alkylation has been used to prepare a number of linkers that permit the attachment of 3,2-HOPO moieties onto various scaffolds using a wide range of coupling methods. The Mitsunobu reaction of 2 with representative alcs. was found to be of limited value due to competing O-alkylation that led to product mixtures The phthalimide 3j (II) can be converted in two steps to HOPO isocyanate 6 (III) in excellent yields. Isocyanate 6 can be coupled to amines at room temperature or to alcs. in refluxing dichloroethane to obtain the corresponding urea or carbamate linked ligand systems. The coupling of isocyanate 6 with TREN followed by deprotection gave the tris-HOPO 10 (IV), an interesting target as it has both cationic and anionic binding sites. The HOPO hydroxylamine linker 11 (V) was shown to be especially valuable as its coupling with carboxylic acids proceeds with the concomitant generation of an addnl. hydroxamate ligand moiety in the framework. The utility of this linker was shown by the preparation of two mixed HOPO-hydroxamate chelators, 16 (VI) and 19 (VII), based on the structure of desferrioxamine, a well-known trihydroxamate siderophore. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4COA of Formula: C13H14BrNO2).

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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.COA of Formula: C13H14BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

1,4-Substituted 4-(1H)-pyridylene-hydrazone-type inhibitors of AChE, BuChE, and amyloid-β aggregation crossing the blood-brain barrier was written by Prinz, Michaela;Parlar, Sulunay;Bayraktar, Gulsah;Alptuzun, Vildan;Erciyas, Ercin;Fallarero, Adyary;Karlsson, Daniela;Vuorela, Pia;Burek, Malgorzata;Forster, Carola;Turunc, Ezgi;Armagan, Guliz;Yalcin, Ayfer;Schiller, Carola;Leuner, Kristina;Krug, Manuel;Sotriffer, Christoph A.;Holzgrabe, Ulrike. And the article was included in European Journal of Pharmaceutical Sciences in 2013.Recommanded Product: 954-81-4 This article mentions the following:

Given the fundamentally multifactorial character of Alzheimer’s disease (AD), addressing more than one target for disease modification or therapy is expected to be highly advantageous. Here, following the cholinergic hypothesis, we aimed to inhibit both acetyl- and butyrylcholinesterase (AChE and BuChE) in order to increase the concentration of acetylcholine in the synaptic cleft. In addition, the formation of the amyloid β fibrils should be inhibited and already preformed fibrils should be destroyed. Based on a recently identified AChE inhibitor with a 1,4-substituted 4-(1H)-pyridylene-hydrazone skeleton, a substance library has been generated and tested for inhibition of AChE, BuChE, and fibril formation. Blood-brain barrier mobility was ensured by a transwell assay. Whereas the p-nitrosubstituted compound 18C shows an anti-AChE activity in the nanomolar range of concentration (IC₅₀ = 90 nM), the bisnaphthyl substituted compound 20L was found to be the best overall inhibitor of AChE/BuChE and enhances the fibril destruction. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Recommanded Product: 954-81-4).

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.Recommanded Product: 954-81-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Nickel-Catalyzed Chain-Walking Cross-Electrophile Coupling of Alkyl and Aryl Halides and Olefin Hydroarylation Enabled by Electrochemical Reduction was written by Kumar, Gadde Sathish;Peshkov, Anatoly;Brzozowska, Aleksandra;Nikolaienko, Pavlo;Zhu, Chen;Rueping, Magnus. And the article was included in Angewandte Chemie, International Edition in 2020.Category: bromides-buliding-blocks This article mentions the following:

The first electrochem. approach for nickel-catalyzed cross-electrophile coupling was developed. This method provides a novel route to 1,1-diarylalkane derivatives from simple and readily available alkyl and aryl halides in good yields and excellent regioselectivity under mild conditions. The procedure shows good tolerance for a broad variety of functional groups and both primary and secondary alkyl halides can be used. Furthermore, the reaction was successfully scaled up to the multigram scale, thus indicating potential for industrial application. Mechanistic study suggested the formation of a nickel hydride in the electroreductive chain-walking arylation, which led to the development of a new nickel-catalyzed hydroarylation of styrenes to provide a series of 1,1-diaryl alkanes in good yields under mild reaction conditions. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Category: bromides-buliding-blocks).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) 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

New Metallo-Supramolecular Terpyridine-Modified Cellulose Functional Nanomaterials was written by Hassan, Mohammad L.;Moorefield, Charles M.;Elbatal, Hany S.;Newkome, George R.. And the article was included in Journal of Macromolecular Science, Part A: Pure and Applied Chemistry in 2012.Application of 954-81-4 This article mentions the following:

New metallo-supramol. nanocellulosic derivatives were prepared by surface modification of cellulose nanocrystals with 4-chloro-2,2′:6′,2”-terpyridine and subsequent coupling with other terpyridine-functionalized derivatives via Ru^III/Ru^II reduction The terpyridine-modified cellulose nanocrystals (CTP) were characterized using transmission electron microscopy (TEM), magic angle spinning ¹³C NMR (MAS-¹³C NMR), elemental anal., as well as Fourier transform IR (FTIR) and UV-Visible spectroscopy. Metallo-CTP with different optical properties, and expected magnetic and catalytic properties, were easily obtained upon reaction of the prepared CTP with different di- and trivalent transition metal ions (Fe⁺², Mn⁺², Co⁺², and Ru⁺³). Metallo-supramol. nanocellulosic derivatives with different properties were prepared by subsequent coupling of Ru^III-CTP complex with other terpyridine ligands bearing different functionalities. In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Application of 954-81-4).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Application of 954-81-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Investigation on the synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones and their biological evaluation against cancer cells was written by Dago, Camille Deliko;Ambeu, Christelle N’ta;Coulibaly, Wacothon Karime;Bekro, Yves-Alain;Mamyrbekova-Bekro, Janat A.;Le Guevel, Remy;Corlu, Anne;Bazureau, Jean-Pierre. And the article was included in Chemistry of Heterocyclic Compounds (New York, NY, United States) in 2017.Reference of 57293-19-3 This article mentions the following:

The 5-step synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones I [X = (CH₂)_n; R = OMe, n = 2; R = H, n = 2; R = OMe, n = 1] without 5-arylidene fragments starting from tyramine was described. The construction involved protection with Boc₂O, regioselective O-alkylation, deprotection with 6 M HCl, neutralization, and finally reaction of bis(carboxymethyl)trithiocarbonate under microwave irradiation The intermediates and the N-substituted rhodanine have been also evaluated for their in vitro inhibition of cell proliferation (Huh7, Caco 2, MDA-MB231, HCT 116, PC3, NCI-H727, HaCat). Two compounds have shown a selective potent activity against HCT116 cell line. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Reference of 57293-19-3).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) 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. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Reference of 57293-19-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary