Month: January 2023

Reaction scope and mechanistic insights of nickel-catalyzed migratory Suzuki-Miyaura cross-coupling was written by Li, Yuqiang;Luo, Yixin;Peng, Long;Li, Yangyang;Zhao, Binzhi;Wang, Wang;Pang, Hailiang;Deng, Yi;Bai, Ruopeng;Lan, Yu;Yin, Guoyin. And the article was included in Nature Communications in 2020.Recommanded Product: 1-(3-Bromopropyl)-4-methoxybenzene This article mentions the following:

In this work, a Ni-catalyzed migratory Suzuki-Miyaura cross-coupling featuring high benzylic or allylic selectivity has been developed. With this method, unactivated alkyl electrophiles and aryl or vinyl boronic acids can be efficiently transferred to diarylalkane or allylbenzene derivatives under mild conditions. Importantly, unactivated alkyl chlorides can also be successfully used as the coupling partners. To demonstrate the applicability of this method, showcase that this strategy can serve as a platform for the synthesis of terminal, partially deuterium-labeled mols. from readily accessible starting materials. Exptl. studies suggest that migratory cross-coupling products are generated from Ni(0/II) catalytic cycle. Theor. calculations indicate that the chain-walking occurs at a neutral nickel complex rather than a cationic one. In addition, the original-site cross-coupling products can be obtained by alternating the ligand, wherein the formation of the products has been rationalized by a radical chain process. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Recommanded Product: 1-(3-Bromopropyl)-4-methoxybenzene).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) 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. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. 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.Recommanded Product: 1-(3-Bromopropyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Palladium-Catalyzed Cross-Coupling Reactions of Benzyl Indium Reagents with Aryl Iodides was written by Chupak, Louis S.;Wolkowski, Joanna P.;Chantigny, Yves A.. And the article was included in Journal of Organic Chemistry in 2009.Application In Synthesis of 3-(Bromomethyl)benzoic acid This article mentions the following:

Herein described is an operationally simple procedure for generating benzyl indium species from readily available benzyl bromides and indium metal followed by in situ palladium-catalyzed coupling with aryl halides. The procedure provides diarylmethanes in modest to excellent yield and tolerates a variety of functional groups in both coupling partners. In the experiment, the researchers used many compounds, for example, 3-(Bromomethyl)benzoic acid (cas: 6515-58-8Application In Synthesis of 3-(Bromomethyl)benzoic acid).

3-(Bromomethyl)benzoic acid (cas: 6515-58-8) 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.Application In Synthesis of 3-(Bromomethyl)benzoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Effects of structural modification of (alkyldiene-imidazolium bromide)-based gemini monomers on the formation of the lyotropic bicontinuous cubic phase was written by Li, Patrick;Reinhardt, Maria I.;Dyer, Samantha S.;Moore, Kara E.;Imran, Omar Q.;Gin, Douglas L.. And the article was included in Soft Matter in 2021.Product Details of 56523-59-2 This article mentions the following:

Seven homologues of an amphiphilic gemini monomer were synthesized and screened for the ability to form a bicontinuous cubic (Q) lyotropic liquid crystal phase. Four of these homologues form a Q phase with glycerol or water that can be cross-linked with retention of the nanoporous structure, with one exhibiting a well-ordered Q phase with a wider phase window than the parent monomer. In the experiment, the researchers used many compounds, for example, 15-Bromopentadecanoic acid (cas: 56523-59-2Product Details of 56523-59-2).

15-Bromopentadecanoic acid (cas: 56523-59-2) 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. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Product Details of 56523-59-2

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

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

Black-to-transmissive polymer films via electrochemical copolymerization with high-performance electrochromic and supercapacitor bifunction was written by Tang, Yixiao;Zhang, Ling;Yan, Shuanma;Kuai, Yu;Fu, Haichang;Li, Weijun;Ouyang, Mi;Zhang, Cheng. And the article was included in Solar Energy Materials & Solar Cells in 2022.Recommanded Product: 128-08-5 This article mentions the following:

The black-to-transmissive electrochromic polymer has significant value with practical applications. Integration of electrochromic and supercapacitor bifunctional materials can indicate its capacitor level by visual color change in real-time. In this paper, based on three EDOT derivative monomers were associated to phenanthrocarbazole/benzotriazole/benzothiadiazole, M1, M2 and M3, a novel ternary random copolymer film was successfully prepared by electrochem. copolymerization Since the corresponding homopolymers of three monomers are red, green and blue in the neutral state resp., and their oxidation states are all transparent, therefore the obtained ternary random copolymer films show the black-to-transmissive electrochromic behavior. The copolymer film pCo-2 was prepared via electrochem. copolymerization with suitable monomers feed ratio (1: 1.5: 1 of M1: M2: M3). Benefit from ternary random electrochem. copolymerization, the pCo-2 copolymer displays excellent electrochromic-supercapacitor properties among the similar bifunctional materials, with fast response time, high optical contrast, good cycling stability and large area (volume) specific capacitance. The electrochromic supercapacitor device based on pCo-2//PEDOT can make an LCD run continuously. This work provides an available general approach to realizing black-to-transmissive electrochromism towards electrochromic-supercapacitor bifunctional applications. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Recommanded Product: 128-08-5).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) 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). 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.Recommanded Product: 128-08-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Transport of Nucleoside Triphosphates into Cells by Artificial Molecular Transporters was written by Zawada, Zbigniew;Tatar, Ameneh;Mocilac, Pavle;Budesinsky, Milos;Kraus, Tomas. And the article was included in Angewandte Chemie, International Edition in 2018.Computed Properties of C42H63Br7O28 This article mentions the following:

Chem. modified nucleoside triphosphates (NTPs) are widely exploited as unnatural metabolites in chem. biol. and medicinal chem. Because anionic NTPs do not permeate cell membranes, their corresponding neutral precursors were employed in cell-based assays. These precursors become active metabolites after enzymic conversion, which often proceeds insufficiently. Metabolically-active NTPs can be directly transported into eukaryotic cells and bacteria by the action of designed synthetic nucleoside triphosphate transporters (SNTTs). The transporter is composed of a receptor, which forms a noncovalent complex with a triphosphate anion, and a cell-penetrating agent, which translocates the complex across the plasma membrane. NTP is then released from the complex in the intracellular milieu and accumulates in nuclei and nucleoli in high concentration The transport of NTPs proceeds rapidly (seconds to minutes) and selectively even in the presence of other organic anions. This operationally simple and efficient means of transport of fluorescently labeled NTPs into cells can be used for metabolic labeling of DNA in live cells. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1Computed Properties of C42H63Br7O28).

Heptakis(6-Bromo-6-Deoxy)-β-Cyclodextrin (cas: 53784-83-1) 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. 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.Computed Properties of C42H63Br7O28

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

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

[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