Month: February 2023

Organic carboxylate salt-enabled alternative synthetic routes for bio-functional cyclic carbonates and aliphatic polycarbonates was written by Watanabe, Yuya;Takaoka, Shunya;Haga, Yuta;Kishi, Kohei;Hakozaki, Shunta;Narumi, Atsushi;Kato, Takashi;Tanaka, Masaru;Fukushima, Kazuki. And the article was included in Polymer Chemistry in 2022.Quality Control of 1-Bromo-4-methoxybutane This article mentions the following:

Simple and efficient synthetic routes for functionalized cyclic carbonates are indispensable for the practical application of side-chain bio-functionalized aliphatic polycarbonates as biodegradable functional biomaterials. In this study, a six-membered cyclic carbonate with a triethylammonium carboxylate has been prepared in one step from 2,2-bis(methylol)propionic acid (bis-MPA). We have demonstrated the suitability of the organic carboxylate salt of the bis-MPA cyclic carbonate for esterification with alkyl bromides via the S_N2 mechanism, leading to the formation of functionalized cyclic carbonate monomers. The esterification of the organic carboxylate salt proceeds efficiently when alkyl bromides with 浼?carbonyl, allyl, and benzyl groups are used. This approach enables a two-step synthesis of functionalized cyclic carbonates from bis-MPA. The organocatalyzed ring-opening polymerization of the resultant functionalized cyclic carbonates is effectively controlled, indicating that the synthetic process involving the organic carboxylate salt does not influence their polymerizability. The ether-functionalized aliphatic polycarbonates obtained from the organic carboxylate salt exhibit good antiplatelet properties, comparable to those of a previously developed blood-compatible aliphatic polycarbonate. The synthetic pathways exploiting organic carboxylate salts enable alternative shortcuts to functionalized cyclic carbonates from bis-MPA. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Quality Control of 1-Bromo-4-methoxybutane).

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鑱砨romine 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.Quality Control of 1-Bromo-4-methoxybutane

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Scalable anti-Markovnikov hydrobromination of aliphatic and aromatic olefins was written by Galli, Marzia;Fletcher, Catherine J.;del Pozo, Marc;Goldup, Stephen M.. And the article was included in Organic & Biomolecular Chemistry in 2016.Recommanded Product: 57293-19-3 This article mentions the following:

To improve access to a key synthetic intermediate a direct hydrobromination-Negishi route was targeted. Unsurprisingly, the anti-Markovnikov addition of HBr to estragole in the presence of AIBN proved successful. However, even in the absence of an added initiator, anti-Markovnikov addition was observed Re-examination of early reports revealed that selective Markovnikov addition, often simply termed “normal” addition, was not always observed with HBr unless air was excluded, leading to the rediscovery of a reproducible and scalable initiator-free protocol. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Recommanded Product: 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. Recommanded Product: 57293-19-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

A Biocatalytic Platform for Synthesis of Chiral 浼?Trifluoromethylated Organoborons was written by Huang, Xiongyi;Garcia-Borras, Marc;Miao, Kun;Kan, S. B. Jennifer;Zutshi, Arjun;Houk, K. N.;Arnold, Frances H.. And the article was included in ACS Central Science in 2019.Safety of 1-(2-Bromoethyl)-4-methoxybenzene This article mentions the following:

There are few biocatalytic transformations that produce fluorine-containing mols. prevalent in modern pharmaceuticals. To expand the scope of biocatalysis for organofluorine synthesis, we have developed an enzymic platform for highly enantioselective carbene B-H bond insertion to yield versatile 浼?trifluoromethylated (浼?CF₃) organoborons, an important class of organofluorine mols. that contain stereogenic centers bearing both CF₃ and boron groups. In contrast to current “carbene transferase” enzymes that use a limited set of simple diazo compounds as carbene precursors, this system based on Rhodothermus marinus cytochrome c (Rma cyt c) can accept a broad range of trifluorodiazo alkanes and deliver versatile chiral 浼?CF₃ organoborons with total turnovers up to 2870 and enantiomeric ratios up to 98.5:1.5. Computational modeling reveals that this broad diazo scope is enabled by an active-site environment that directs the alkyl substituent on the heme CF₃-carbene intermediate toward the solvent-exposed face, thereby allowing the protein to accommodate diazo compounds with diverse structural features. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Safety of 1-(2-Bromoethyl)-4-methoxybenzene).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) 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. 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.Safety of 1-(2-Bromoethyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Undecahydro-closo-dodecaborates as good leaving groups in organic synthesis: generation of substituted styrenes via elimination of arylethyl dodecaborates was written by Genady, Afaf R.;Nakamura, Hiroyuki. And the article was included in Organic & Biomolecular Chemistry in 2010.COA of Formula: C9H11BrO This article mentions the following:

New functionalized arylethyl undecahydro-closo-dodecaborates (S,S-disubstituted [B₁₂H₁₁SH]^2-, N,N-disubstituted [B₁₂H₁₁NH₃]^– and O-substituted [B₁₂H₁₁OH]^2-) are prepared by a simple one-step reaction. Moderate to good yields are obtained in the presence of various functional aryl groups. The synthesis of functionalized styrene derivatives can be readily achieved by treating arylethyl undecahydro-closo-dodecaborates with various bases. The scope and limitations of this procedure are demonstrated by investigating an array of alkylated dodecaborates. Based on an E2 elimination reaction, we identify the mechanistic pathway for dealkylation of arylethyl dodecaborates. Mechanistic studies indicate the following essential requirements to promote the elimination reaction: (i) the presence of 浼?CH acidity of the phenethyl group; (ii) steric hindrance; (iii) a substituted heteroatom on the closo-[B₁₂H₁₁]^2- cage and (iv) the presence of an electron-withdrawing group on the aromatic ring. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0COA of Formula: C9H11BrO).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.COA of Formula: C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and biological evaluation of novel dimiracetam derivatives useful for the treatment of neuropathic pain was written by Farina, Carlo;Gagliardi, Stefania;Ghelardini, Carla;Martinelli, Marisa;Norcini, Monica;Parini, Carlo;Petrillo, Paola;Ronzoni, Silvano. And the article was included in Bioorganic & Medicinal Chemistry in 2008.Recommanded Product: 3-Bromo-4-fluorotoluene This article mentions the following:

Chem. modifications of dimiracetam (I), a bicyclic analog of the nootropic drug piracetam, afforded a small set of novel derivatives that were investigated in in vivo models of neuropathic pain. Compounds 5, 7 and 8 displayed a very promising antihyperalgesic profile in rat models of neuropathic pain induced by both chronic constriction injury of the sciatic nerve and streptozotocin. The compounds completely reverted the reduction of pain threshold evaluated by the paw pressure test. Importantly these derivatives did not induce any behavioral impairment as evaluated by the rotarod test. These results suggest that compounds 5, 7 and 8 might represent novel and well-tolerated therapeutic agents for the relief of neuropathic pain. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-fluorotoluene (cas: 452-62-0Recommanded Product: 3-Bromo-4-fluorotoluene).

3-Bromo-4-fluorotoluene (cas: 452-62-0) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Recommanded Product: 3-Bromo-4-fluorotoluene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Dynamic Kinetic Resolution of Biaryl Atropisomers via Peptide-Catalyzed Asymmetric Bromination was written by Gustafson, Jeffrey L.;Lim, Daniel;Miller, Scott J.. And the article was included in Science (Washington, DC, United States) in 2010.Safety of Methyl 2-bromo-4-fluorobenzoate This article mentions the following:

Despite the widespread use of axially chiral, or atropisomeric, biaryl ligands in modern synthesis and the occurrence of numerous natural products exhibiting axial chirality, few catalytic methods have emerged for the direct asym. preparation of this compound class. Here, the authors present a tripeptide-derived small-mol. catalyst for the dynamic kinetic resolution of racemic biaryl substrates. The reaction proceeds via an atropisomer-selective electrophilic aromatic substitution reaction using simple bromination reagents. The result is an enantioselective synthesis that delivers chiral nonracemic biaryl compounds with excellent optical purity and good isolated chem. yields (in most cases a >95:5 enantiomer ratio and isolated yields of 65 to 87%). A mechanistic model is advanced that accounts for the basis of selectivity observed In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9Safety 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閳ユ彽romine 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.Safety of Methyl 2-bromo-4-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tricyclic pharmacophore-based molecules as novel integrin 浼?sub>v灏?sub>3 antagonists. Part IV: Preliminary control of 浼?sub>v灏?sub>3 selectivity by meta-oriented substitution was written by Kubota, Dai;Ishikawa, Minoru;Ishikawa, Midori;Yahata, Naokazu;Murakami, Shoichi;Fujishima, Kazuyuki;Kitakaze, Masafumi;Ajito, Keiichi. And the article was included in Bioorganic & Medicinal Chemistry in 2006.Formula: C8H6BrFO2 This article mentions the following:

To establish the in vivo efficacy of 浼?sub>v灏?sub>3/浼?sub>IIb灏?sub>3 dual antagonists possessing a tricyclic pharmacophore, a corresponding 浼?sub>v灏?sub>3-selective antagonist was required as a control. We initially took two synthetic approaches to obtain 浼?sub>v灏?sub>3-selective antagonists based on the RGD recognition pattern or on modification of the dihedral angle between the central benzene ring and the adjacent heterocycle, but both proved unsuccessful. However, synthesis of novel antagonists with meta-substitution of the central benzene ring generated weak selectivity for 浼?sub>v灏?sub>3 over 浼?sub>IIb灏?sub>3 for the first time in the family of compounds with the tricyclic pharmacophore. Optimization of meta-oriented antagonists furnished an 浼?sub>v灏?sub>3-selective antagonist exhibiting inhibitory activity not only in a receptor-binding assay, but also in a cell adhesion assay. In the experiment, the researchers used many compounds, for example, Methyl 3-bromo-5-fluorobenzoate (cas: 334792-52-8Formula: C8H6BrFO2).

Methyl 3-bromo-5-fluorobenzoate (cas: 334792-52-8) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon閳ユ彽romine 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: C8H6BrFO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Terminal Trifluoromethylation of Ketones via Selective C-C Cleavage of Cycloalkanols Enabled by Hypervalent Iodine Reagents was written by Wu, Shuang;Li, Junzhao;He, Ru;Jia, Kunfang;Chen, Yiyun. And the article was included in Organic Letters in 2021.Synthetic Route of C10H13BrO This article mentions the following:

The first terminal trifluoromethylation at aryl and alkyl ketone’s 绾? 鏈? 钄? or more remote sites via selective C-C bond cleavage of cycloalkanols was reported. The noncovalent interactions between alcs. and hypervalent iodines(III) reagents were disclosed to activate both alcs. and the Togni I reagent in the dual photoredox/copper catalysis for the transformation. This reaction was scalable to the gram-scale synthesis, applicable to the structurally complex steroid trifluoromethylation, and extendable to the pentafluoroethylation. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Synthetic Route of C10H13BrO).

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. 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.Synthetic Route of C10H13BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

4-Alkyloxyimino Derivatives of Uridine-5′-triphosphate: Distal Modification of Potent Agonists as a Strategy for Molecular Probes of P2Y₂, P2Y₄, and P2Y₆ Receptors was written by Jayasekara, P. Suresh;Barrett, Matthew O.;Ball, Christopher B.;Brown, Kyle A.;Hammes, Eva;Balasubramanian, Ramachandran;Harden, T. Kendall;Jacobson, Kenneth A.. And the article was included in Journal of Medicinal Chemistry in 2014.Name: 1-(3-Bromopropyl)-4-methoxybenzene This article mentions the following:

Extended N⁴-(3-arylpropyl)oxy derivatives of uridine-5′-triphosphate were synthesized and potently stimulated phospholipase C stimulation in astrocytoma cells expressing G protein-coupled human (h) P2Y receptors (P2YRs) activated by UTP (P2Y_2/4R) or UDP (P2Y₆R). The potent P2Y₄R-selective N⁴-(3-phenylpropyl)oxy agonist was Ph ring-substituted or replaced with terminal heterocyclic or naphthyl rings with retention of P2YR potency. This broad tolerance for steric bulk in a distal region was not observed for dinucleoside tetraphosphate agonists with both nucleobases substituted. The potent N⁴-(3-(4-methoxyphenyl)-propyl)oxy analog I (EC₅₀: P2Y₂R, 47 nM; P2Y₄R, 23 nM) was functionalized for chain extension using click tethering of fluorophores as prosthetic groups. The BODIPY conjugate exhibited EC₅₀ values of 70, 66, and 23 nM at the hP2Y_2/4/6Rs, resp., and specifically labeled cells expressing the P2Y₆R. Thus, an extended N⁴-(3-arylpropyl)oxy group accessed a structurally permissive region on three G_q-coupled P2YRs, and potency and selectivity were modulated by distal structural changes. This freedom of substitution was utilized to design of a pan-agonist fluorescent probe of a subset of uracil nucleotide-activated hP2YRs. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Name: 1-(3-Bromopropyl)-4-methoxybenzene).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) 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鑱砨romine bond is electrophilic in nature. 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: 1-(3-Bromopropyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis was written by Guo, Lei;Yuan, Mingbin;Zhang, Yanyan;Wang, Fang;Zhu, Shengqing;Gutierrez, Osvaldo;Chu, Lingling. And the article was included in Journal of the American Chemical Society in 2020.COA of Formula: C8H6BrFO2 This article mentions the following:

A visible-light-promoted photoredox/nickel protocol for the enantioselective three-component carboarylation of alkenes with tertiary and secondary alkyltrifluoroborates and aryl bromides is described. This redox-neutral protocol allows for facile and divergent access to a wide array of enantioenriched 灏?alkyl-浼?arylated carbonyls, phosphonates, and sulfones in high yields and excellent enantioselectivities from readily available starting materials. We also report a modular and enantioselective synthesis of flurbiprofen analogs and piragliatin lead compound to demonstrate synthetic utility. Exptl. and computational mechanistic studies were performed to gain insights into the mechanism and origin of chemo- and enantioselectivity. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2COA of Formula: C8H6BrFO2).

Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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.COA of Formula: C8H6BrFO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary