Category: bromides-buliding-blocks

Design, synthesis and insecticide activity of novel acetylcholinesterase inhibitors: triazolinone and phthalimide heterodimers was written by Xie, Ruliang;Mei, Xiangdong;Ning, Jun. And the article was included in Chemical & Pharmaceutical Bulletin in 2019.COA of Formula: C13H14BrNO2 This article mentions the following:

A new series of 1,2,4-triazolin-3-one and phthalimide heterodimers I [X = (CH₂)_n; n = 1, 2, 9, etc.] was synthesized and evaluated for their insecticidal and acetylcholinesterase inhibitory activities. Most of the synthesized compounds I showed good in vitro inhibitory activities against both Drosophila melanogaster acetylcholinesterase (DmAChE) and Musca domestica acetylcholinesterase (MdAChE). Among them, compound I (n = 7) was found to be most potent AChE inhibitor (IC₅₀ = 8.07 娓璏 to DmAChE, IC₅₀ = 32.24 娓璏 to MdAChE), whose activities were 2.31- and 1.35-fold more active than the pos. control ethion (CP, IC₅₀ = 18.62 娓璏 to DmAChE, IC₅₀ = 43.56 娓璏 to MdAChE). The docking model study revealed that compound I (n = 7) possessed fitted spatial structure and bound to central pocket and peripheral site of DmAChE. Moreover, most of the compounds I demonstrated high insecticidal activity to Lipaphis erysimi and Tetranychus cinnabarinus at concentration of 300 mg/L. 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. 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). 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.COA of Formula: C13H14BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Asymmetric Michael addition catalyzed by D-glucose-based azacrown ethers was written by Novak, Tibor;Tatai, Janos;Bako, Peter;Czugler, Matyas;Keglevich, Gyorgy;Toke, Laszlo. And the article was included in Synlett in 2001.Formula: C13H14BrNO2 This article mentions the following:

Novel sugar-based azacrown ethers with phosphinoxidoalkyl side-chain were synthesized. They show asym. induction as phase-transfer catalysts in the Michael addition of 2-nitropropane to chalcone (95% ee) and to 3-fur-2-yl-1-phenyl-2-propen-1-one (80% ee). In the experiment, the researchers used many compounds, for example, N-(5-Bromopentyl)phthalimide (cas: 954-81-4Formula: C13H14BrNO2).

N-(5-Bromopentyl)phthalimide (cas: 954-81-4) 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). 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.Formula: C13H14BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Graphene Oxide-Supported Hypervalent Organoiodine (III): Recyclable Reagent for Selective and Metal-Free Oxidation of Alcohols was written by Ghanbari, Nastaran;Ghafuri, Hossein;Zand, Hamid Reza Esmaili. And the article was included in ChemistrySelect in 2018.Electric Literature of C7H7BrO2 This article mentions the following:

In this research, main emphasis has been placed on the oxidizing properties of graphene oxide (GO) and hypervalent organoiodine (III) (HVI) and their oxidizing effect in GO-HVI. GO-HVI as a metal-free, environmentally-friendly, recyclable and efficient heterogeneous reagent was synthesized and completely characterized by Fourier transform IR spectroscopy (FT-IR), energy dispersive X-ray (EDX), field emission SEM (FE-SEM), X-ray diffraction, and at. force microscopy (AFM). The synthesized GO-HVI was used to achieve an effective and selective method for oxidation of various alcs. All substituted alcs. were oxidized in good to excellent yields under mild conditions at room temperature The oxidizing ability of GO-HVI was higher in comparison with starting GO and HVI. This GO-HVI have great stability and could be recycled six times without noteworthy loss of activity. In the experiment, the researchers used many compounds, for example, 5-Bromo-2-(hydroxymethyl)phenol (cas: 170434-11-4Electric Literature of C7H7BrO2).

5-Bromo-2-(hydroxymethyl)phenol (cas: 170434-11-4) 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.Electric Literature of C7H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Building fluorescent sensors by template polymerization: the preparation of a fluorescent sensor for D-fructose was written by Wang, Wei;Gao, Shouhai;Wang, Binghe. And the article was included in Organic Letters in 1999.Product Details of 166821-88-1 This article mentions the following:

The application of mol. imprinting in making fluorescent sensors was hampered by the lack of suitable fluorescent tags, which would respond to the binding event with significant fluorescence intensity changes. The authors have designed and synthesized a fluorescent monomer which allows for the preparation of fluorescent sensors of cis diols using mol. imprinting methods. This monomer was used for the preparation of sensitive fluorescent sensors for D-fructose. In the experiment, the researchers used many compounds, for example, 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1Product Details of 166821-88-1).

2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1) 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Product Details of 166821-88-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Carbonylation of bromo(bromomethyl)benzenes to alkyl carboalkoxyphenylacetates catalyzed by cobalt carbonyl was written by Shim, Sang Chul;Doh, Chil Hoon;Lee, Dong Yub;Youn, Young Zoo;Lee, Seung Yub;Chae, Shin Ae;Oh, Dae Hee;Oh, Hunseung. And the article was included in Bulletin of the Korean Chemical Society in 1992.Synthetic Route of C10H11BrO2 This article mentions the following:

Carbonylation of bromo(bromomethyl)benzene catalyzed by cobalt carbonyl gave (alkoxycarbonyl)phenylacetates. Carbonylation of 1-bromo-4-(bromomethyl)benzene with CO/Co₂(CO)₈/EtOH/MeI gave 98% Et [4-(ethoxycarbonyl)phenyl]acetate. The effects of base and alcs. in this reaction were examined In the experiment, the researchers used many compounds, for example, Ethyl (2-bromophenyl)acetate (cas: 2178-24-7Synthetic Route of C10H11BrO2).

Ethyl (2-bromophenyl)acetate (cas: 2178-24-7) 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. 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.Synthetic Route of C10H11BrO2

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

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

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

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

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