Month: February 2023

Palladium(0) catalyzed cross coupling reactions of hindered, double activated aryl halides with organozinc reagents – the effect of copper(I) cocatalysis was written by Weichert, Andreas;Bauer, Martina;Wirsig, Petra. And the article was included in Synlett in 1996.Safety of Methyl 4-bromo-3-(trifluoromethyl)benzoate This article mentions the following:

Various organozinc reagents undergo palladium(0) catalyzed Negishi-Kumada-type cross coupling reactions, cocatalyzed by copper(I) iodide, with electronically activated aryl halides in the presence of an electron withdrawing ortho or meta substituent and an ester group. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8Safety of Methyl 4-bromo-3-(trifluoromethyl)benzoate).

Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8) 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.Safety of Methyl 4-bromo-3-(trifluoromethyl)benzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Efficient Access to Methyl-1-hydroxy-2-naphthoates and Heterocyclic Analogues was written by Podeschwa, Michael A. L.;Rossen, Kai. And the article was included in Organic Process Research & Development in 2015.Quality Control of Methyl 2-bromo-4-fluorobenzoate This article mentions the following:

We report the synthesis of Me 1-hydroxy-2-naphthoate derivatives and heterocyclic analogs using a two-step approach. This short route employs a Heck coupling of a 2-halobenzoate with Me 3-butenoate followed by a Dieckmann cyclization, yielding the 1-hydroxynaphthalene-2-carboxylic acid derivatives in the multigram scale. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9Quality Control of Methyl 2-bromo-4-fluorobenzoate).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon闂佺偨鍎茶ぐ绲﹐mine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Quality Control of Methyl 2-bromo-4-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Radical 1,4-Aryl Migration Enabled Remote Cross-Electrophile Coupling of 濞?Amino-閻?Bromo Acid Esters with Aryl Bromides was written by Tang, Shi;Xu, Zhen-Hua;Liu, Ting;Wang, Shuo-Wen;Yu, Jian;Liu, Jian;Hong, Yu;Chen, Shi-Lu;He, Jin;Li, Jin-Heng. And the article was included in Angewandte Chemie, International Edition in 2021.Synthetic Route of C8H7BrO2 This article mentions the following:

Here an unprecedented, efficient nickel-catalyzed radical relay was reported for the remote cross-electrophile coupling of 閻?bromo-濞?benzylamino acid esters with aryl bromides via 1,4-aryl migration/arylation cascades. 閻?Bromo-濞?benzylamino acid esters were considered as unique mol. scaffolds allowing for aryl migration reactions, which were conceptually novel variants for the radical Truce-Smiles rearrangement. This reaction enabled the formation of two new C(sp3)-C(sp2) bonds using a bench-stable Ni/bipyridine/Zn system featuring a broad substrate scope and excellent diastereoselectivity, which provided an effective platform for the remote aryl group migration and arylation of amino acid esters via redox-neutral C(sp3)-C(sp2) bond cleavage. Mechanistically, this cascade reaction was accomplished by combining two powerful catalytic cycles consisting of a cross-electrophile coupling and radical 1,4-aryl migration through the generation of C(sp3)-centered radical intermediates from the homolysis of C(sp3)-Br bonds and the switching of the transient alkyl radical into a robust 濞?aminoalkyl radical. In the experiment, the researchers used many compounds, for example, 3-Bromophenyl acetate (cas: 35065-86-2Synthetic Route of C8H7BrO2).

3-Bromophenyl acetate (cas: 35065-86-2) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon闂佺偨鍎茶ぐ绲﹐mine 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.Synthetic Route of C8H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of compounds allied to rhododendrin was written by Kim, Ki-U. And the article was included in Yakugaku Zasshi in 1943.HPLC of Formula: 57293-19-3 This article mentions the following:

In order to exam. the pharmacol. action of compounds allied to rhododendrin, the following compounds were synthesized. 1-(p-Hydroxyphenyl)-2-propanol: p-MeOC₆H₄CH:CHMe(+ Br) 闂?MeOC₆H₄CHBrCHBrMe (+ CaO) 闂?MeOC₆H₄CH(OH)CHBrMe (+ 2.5% alkali) 闂?MeOC₆H₄CH(OH)CH(OH)Me (heating to 180闁? 闂?MeOC₆H₄CH₂COMe (+ Na + EtOH) 闂?MeOC₆H₄CH₂CH(OH)Me (+ Grignard reagent) 闂?p-HOC₆H₄CH₂CH(OH)Me. 5-(p-Hydroxyphenyl)-2-pentanol: p-MeOC₆H₄CHO + AcOEt (+ Na) 闂?MeOC₆H₄CH:CHCO₂Et (+ H) 闂?MeOC₆H₄CH₂CH₂CO₂Et (+ Na + AmOH) 闂?MeOC₆H₄(CH₂)₃OH (+ PBr₃) 闂?MeOC₆H₄(CH₂)₃Br 闂?MeOC₆H₄(CH₂)₃CN (+ MeMgI) 闂?MeOC₆H₄(CH₂)₃COMe 闂?MeOC₆H₄(CH₂)₃CH(OH)Me 闂?HOC₆H₄(CH₂)₃CH(OH)Me. By similar methods were prepared: 6-(p-hydroxyphenyl)-2-hexanol, from p-MeOC₆H₄CHO and EtCOMe; 1-(m-hydroxyphenyl)-3-butanol, from m-MeOC₆H₄CHO and Me₂CO; 1-(4-hydroxy-3-methoxyphenyl)-3-butanol, from vanillin and Me₂CO; 1-(p-hydroxyphenyl)-3-pentanol, from p-MeOC₆H₄CHO and AcOEt; 1-(4-hydroxy-3-methylphenyl)-3-butanol from 3,4-Me(HO)C₆H₃CHO (prepared from m-MeC₆H₄OH, HCN, AlCl₃, and HCl) and Me₂CO; 1-(4-hydroxy-2-methylphenyl)-3-butanol, from 2,4-Me(HO)C₆H₃CHO and Me₂CO; and 1-(4-hydroxy-5-isopropyl-2-methylphenyl)-3-butanol, from 5,2-Me(Me₂CH)C₆H₃OH through 2,5,4-Me(Me₂CH)(HO)C₆H₂CHO. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3HPLC of Formula: 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. HPLC of Formula: 57293-19-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The nickel(II)-catalyzed direct benzylation, allylation, alkylation, and methylation of C-H bonds in aromatic amides containing an 8-aminoquinoline moiety as the directing group was written by Aihara, Yoshinori;Wuelbern, Jendrik;Chatani, Naoto. And the article was included in Bulletin of the Chemical Society of Japan in 2015.Related Products of 4457-67-4 This article mentions the following:

Direct alkylation via the cleavage of the ortho C-H bonds by a nickel-catalyzed reaction of aromatic amides containing an 8-aminoquinoline moiety as the directing group with alkyl halides is reported. Various alkyl halides, including benzyl, allyl, alkyl, and Me halides (or pseudo halides) participate as electrophilic coupling partners. The reaction shows a high functional group compatibility. The reaction proceeds in a highly regioselective manner at the less hindered C-H bonds in the reaction of meta-substituted aromatic amides, irresp. of the electronic nature of the substituent. The mechanism responsible for the C-H alkylation reaction is discussed based on the results obtained in a variety of mechanistic experiments In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Related Products of 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) 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闁艰京鐗梤omine bond is electrophilic in nature. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Related Products of 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Metal-Free Aerobic Oxidative Selective C-C Bond Cleavage in Heteroaryl-Containing Primary and Secondary Alcohols was written by Xia, Anjie;Qi, Xueyu;Mao, Xin;Wu, Xiaoai;Yang, Xin;Zhang, Rong;Xiang, Zhiyu;Lian, Zhong;Chen, Yingchun;Yang, Shengyong. And the article was included in Organic Letters in 2019.Application of 18791-79-2 This article mentions the following:

A transition-metal-free aerobic oxidative selective C-C bond-cleavage reaction in primary and secondary heteroaryl alcs. is reported. This reaction was highly efficient and tolerated various heteroaryl alcs., generating a carboxylic acid derivative and a neutral heteroaromatic compound Exptl. studies combined with d. functional theory calculations revealed the mechanism underlying the selective C-C bond cleavage. This strategy also provides an alternative simple approach to carboxylation reaction. In the experiment, the researchers used many compounds, for example, 5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2Application of 18791-79-2).

5-Bromothiophene-3-carbaldehyde (cas: 18791-79-2) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Application of 18791-79-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Molecular organization in the 6-bromo-6-deoxycyclodextrins, formation of molecular layers, and the first crystal structure of a selectivity perfunctionalized 閻?cyclodextrin was written by Nicolis, Ioannis;Coleman, Anthony W.;Charpin, Pierrette;Villain, Francoise;Zhang, Ping;Ling, Chang Chung;de Rango, Colette. And the article was included in Journal of the American Chemical Society in 1993.Synthetic Route of C42H63Br7O28 This article mentions the following:

6-Bromo-6-deoxycyclodextrins form stable monomol. at the air-H₂O interface, with mol. areas of 180, 220 and 260 闁?sup>2 for 濞?, 閻? and 缂?Br-CD. In the case of the heptakis-bromo-閻?CD compound 3 dimensional crystal structure was determined The heptakis-Br-閻?CD compound is monoclinic, space group P2₁, with a 15.714(3), b 15.917(6), c 30.102(4) 闁? 閻?90.55(2)闁? Z = 2. The structure is as a novel packing of dimeric 閻?cyclodextrin systems in a square arrangement. The layers are held together by Br-Br Van der Waals interactions giving rise to a quasi-continuous hydrophobic interface between the layers. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-閻?Cyclodextrin (cas: 53784-83-1Synthetic Route of C42H63Br7O28).

Heptakis(6-Bromo-6-Deoxy)-閻?Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon闂佺偨鍎茶ぐ绲﹐mine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Synthetic Route of C42H63Br7O28

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Role of Molecular Weight in the Mechanical Properties and Charge Transport of Conjugated Polymers Containing Siloxane Side Chains was written by Huang, Gang;Wu, Ning;Wang, Xiaohong;Zhang, Guobing;Qiu, Longzhen. And the article was included in Macromolecular Rapid Communications in 2022.Electric Literature of C4H4BrNO2 This article mentions the following:

The mol. weight is a key factor affecting the properties of conjugated polymers. To determine the critical mol. weights of conjugated polymers modified with siloxane side chains, poly(diketo-pyrrolopyrrole-selenophene) (PTDPPSe-5Si) samples with mol. weights ranging from 20 to 350 kDa are synthesized. The critical mol. weight of the polymer is determined in the range of 60-100 kDa by testing the viscosity of the solution When the mol. weight of the 27-60 kDa polymers is below the critical mol. weight, they exhibit a high crystallinity and low ductility. When the mol. weight of the 100 kDa polymer reaches the critical mol. weight, the crystallinity decreases, and the ductility increases. As the mol. weight increases, the polymer film also gradually changes from brittle to ductile. Furthermore, when the mol. weight of the 315 kDa polymer is much higher than the critical mol. weight, the film exhibits a significant ductility, which results in the polymer films showing no pronounced cracks after high-percentage stretching. Addnl., due to the oriented alignment of the mol. chains caused by stretching, the carrier mobility in the parallel direction becomes 2.14-fold of the initial film. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Electric Literature of C4H4BrNO2).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon闂佺偨鍎茶ぐ绲﹐mine 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.Electric Literature of C4H4BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

3-(2-Carboxyethyl)indole-2-carboxylic Acid Derivatives: Structural Requirements and Properties of Potent Agonists of the Orphan G Protein-Coupled Receptor GPR17 was written by Baqi, Younis;Pillaiyar, Thanigaimalai;Abdelrahman, Aliaa;Kaufmann, Olesja;Alshaibani, Samer;Rafehi, Muhammad;Ghasimi, Saman;Akkari, Rhalid;Ritter, Kirsten;Simon, Katharina;Spinrath, Andreas;Kostenis, Evi;Zhao, Qiang;Kose, Meryem;Namasivayam, Vigneshwaran;Muller, Christa E.. And the article was included in Journal of Medicinal Chemistry in 2018.Formula: C6H5BrClN This article mentions the following:

The orphan receptor GPR17 may be a novel drug target for inflammatory diseases. 3-(2-Carboxyethyl)-4,6-dichloro-1H-indole-2-carboxylic acid (MDL29,951, 1) was previously identified as a moderately potent GPR17 agonist. In the present study, we investigated the structure-activity relationships (SARs) of 1. Substitution of the indole 1-, 5-, or 7-position was detrimental. Only small substituents were tolerated in the 4-position while the 6-position accommodated large lipophilic residues. Among the most potent compounds were 3-(2-carboxyethyl)-1H-indole-2-carboxylic acid derivatives containing the following substituents: 6-phenoxy (26, PSB-1737, EC₅₀ 270 nM), 4-fluoro-6-bromo (33, PSB-18422, EC₅₀ 27.9 nM), 4-fluoro-6-iodo (35, PSB-18484, EC₅₀ 32.1 nM), and 4-chloro-6-hexyloxy (43, PSB-1767, EC₅₀ 67.0 nM). (3-(2-Carboxyethyl)-6-hexyloxy-1H-indole-2-carboxylic acid (39, PSB-17183, EC₅₀ 115 nM) behaved as a partial agonist. Selected potent compounds tested at human P2Y receptor subtypes showed high selectivity for GPR17. Docking into a homol. model of the human GPR17 and mol. dynamic simulation studies rationalized the observed SARs. In the experiment, the researchers used many compounds, for example, 3-Bromo-5-chlorophenylamine (cas: 96558-78-0Formula: C6H5BrClN).

3-Bromo-5-chlorophenylamine (cas: 96558-78-0) 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闁艰京鐗梤omine bond is electrophilic in nature. 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.Formula: C6H5BrClN

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Phenotypic Screening-Based Identification of 3,4-Disubstituted Piperidine Derivatives as Macrophage M2 Polarization Modulators: An Opportunity for Treating Multiple Sclerosis was written by Weng, Qinjie;Che, Jinxin;Zhang, Zhikang;Zheng, Jiahuan;Zhan, Wenhu;Lin, Sendong;Tian, Tian;Wang, Jincheng;Gai, Renhua;Hu, Yongzhou;Yang, Bo;He, Qiaojun;Dong, Xiaowu. And the article was included in Journal of Medicinal Chemistry in 2019.Reference of 179232-29-2 This article mentions the following:

Multiple sclerosis (MS) is a disease of the autoimmune-mediated disorder in the central nervous system, for which no effective therapeutic agent is currently available. The regulation of macrophage polarization toward M2 is a general benefit for treating MS. The gene biomarker-based phenotypic screening approach was developed, and 3,4-disubstituted piperidine derivative S-28 was identified as a lead compound modulating macrophage M2 polarization. Further SAR studies resulted in the discovery of the most potent modulator D11 that showed good oral bioavailability and significant in vivo therapeutic effects. Mechanistic studies demonstrated that the M2 polarization macrophages modulated by D11 mainly functioned through inhibiting the proliferation of T-cells and activating the phosphorylation of Stat3 and Akt. Therefore, the gene biomarker-based phenotypic screening was demonstrated as a promising tool for the discovery of novel macrophage M2 polarization modulators. Compound D11 may serve as a promising starting point for the development of therapeutics to treat MS. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2Reference of 179232-29-2).

Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2) 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. 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.Reference of 179232-29-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary