Tag: 100-200

In 2022,Kundu, Gourab; Opincal, Filip; Sperger, Theresa; Schoenebeck, Franziska published an article in Angewandte Chemie, International Edition. The title of the article was 《Air-Stable PdI Dimer Enabled Remote Functionalization: Access to Fluorinated 1,1-Diaryl Alkanes with Unprecedented Speed》.Recommanded Product: 7073-94-1 The author mentioned the following in the article:

This work features a remote arylation in less than 10 min reaction time at room temperature over a distance of up to 11 carbons. The unprecedented speed was enabled by the air-stable PdI dimer [Pd(μ-I)(PCy2t-Bu)]2, which in contrast to its PtBu3 counterpart does not trigger direct coupling at the initiation site, but regioconvergent and chemoselective remote functionalization to yield valuable fluorinated 1,1-diaryl alkanes. This study combined exptl. and computational studies rationalize the origins of switchability, which were primarily due to differences in dispersion interactions. In the experiment, the researchers used 1-Bromo-2-isopropylbenzene(cas: 7073-94-1Recommanded Product: 7073-94-1)

1-Bromo-2-isopropylbenzene(cas: 7073-94-1) belongs to organobromine compounds.The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. Recommanded Product: 7073-94-1 Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2022,Lamiable-Oulaidi, Farah; Harijan, Rajesh K.; Shaffer, Karl J.; Crump, Douglas R.; Sun, Yan; Du, Quan; Gulab, Shivali A.; Khan, Ashna A.; Luxenburger, Andreas; Woolhouse, Anthony D.; Sidoli, Simone; Tyler, Peter C.; Schramm, Vern L. published an article in Journal of Medicinal Chemistry. The title of the article was 《Synthesis and Characterization of Transition-State Analogue Inhibitors against Human DNA Methyltransferase 1》.Safety of Methyl 3-bromopropanoate The author mentioned the following in the article:

Hypermethylation of CpG regions by human DNA methyltransferase 1 (DNMT1) silences tumor-suppression genes, and inhibition of DNMT1 can reactivate silenced genes. The 5-azacytidines are approved inhibitors of DNMT1, but their mutagenic mechanism limits their utility. A synthon approach from the analogs of S-adenosylhomocysteine, methionine, and deoxycytidine recapitulated the chem. features of the DNMT1 transition state in the synthesis of 16 chem. stable transition-state mimics. Inhibitors causing both full and partial inhibition of purified DNMT1 were characterized. The inhibitors show modest selectivity for DNMT1 vs. DNMT3b. Active-site docking predicts inhibitor interactions with S-adenosyl-L-methionine and deoxycytidine regions of the catalytic site, validated by direct binding anal. Inhibitor action with purified DNMT1 is not reflected in cultured cells. A partial inhibitor activated cellular DNA methylation, and a full inhibitor had no effect on cellular DNA methylation. These compounds provide chem. access to a new family of noncovalent DNMT chem. scaffolds for use in DNA methyltransferases. In the experimental materials used by the author, we found Methyl 3-bromopropanoate(cas: 3395-91-3Safety of Methyl 3-bromopropanoate)

Methyl 3-bromopropanoate(cas: 3395-91-3) belongs to bromides. 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.Safety of Methyl 3-bromopropanoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Chen, Haifeng; Yue, Huifeng; Zhu, Chen; Rueping, Magnus published an article in 2022. The article was titled 《Reactivity in Nickel-Catalyzed Multi-component Sequential Reductive Cross-Coupling Reactions》, and you may find the article in Angewandte Chemie, International Edition.SDS of cas: 7051-34-5 The information in the text is summarized as follows:

The nickel-catalyzed three-component reductive carbonylation of alkyl halides, aryl halides, and Et chloroformate is described. Et chloroformate is utilized as a safe and readily available source of CO in this multi-component protocol, providing an efficient and practical alternative for the synthesis of aryl-alkyl ketones. The reaction exhibits a wide substrate scope and good functional group compatibility. Exptl. and DFT mechanistic studies highlight the complexity of the cross-electrophile coupling and provide insight into the sequence of the three consecutive oxidative additions of aryl halide, chloroformate, and alkyl halide.(Bromomethyl)cyclopropane(cas: 7051-34-5SDS of cas: 7051-34-5) was used in this study.

(Bromomethyl)cyclopropane(cas: 7051-34-5) is used as a synthetic building block for the introduction of the cyclopropylmethyl group. It was also used in the synthesis of 1,4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents.SDS of cas: 7051-34-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Hosseinijei, Reyhaneh; Zahedian Tejeneki, Hossein; Nikbakht, Ali; Rominger, Frank; Balalaie, Saeed published an article in 2022. The article was titled 《Synthesis of functionalized 1-aminoisoquinolines through cascade three-component reaction of ortho-alkynylbenzaldoximes, 2H-azirines, and electrophiles》, and you may find the article in Organic & Biomolecular Chemistry.Synthetic Route of C7H5BrO The information in the text is summarized as follows:

A new three-component approach using ortho-alkynylbenzaldoximes involving the formation of a cyclic nitrone in the presence of Br2 or ICl for the synthesis of 1-aminoisoquinolines via cascade 6-endo-cyclization, 1,3-dipolar cycloaddition reaction with 2H-azirines, and ring-opening reaction sequences was reported. The broad range of structurally diverse products, good to high yields, high atom-economy and high bond-formation efficiency made this method an attractive alternative for the synthesis of 1-aminoisoquinolines.o-Bromobenzaldehyde(cas: 6630-33-7Synthetic Route of C7H5BrO) was used in this study.

o-Bromobenzaldehyde(cas: 6630-33-7) is used in L-threonine aldolase-catalyzed enantio/diastereoselective aldol reactions.Synthetic Route of C7H5BrOIt is a key starting material in the total synthesis of an anticancer agent, (-)-taxol.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2019,Journal of the Iranian Chemical Society included an article by Filian, Hossein; Ghorbani-Choghamarani, Arash; Tahanpesar, Elham. HPLC of Formula: 6630-33-7. The article was titled 《Ni-guanidine@MCM-41 NPs: a new catalyst for the synthesis of 4,4′-(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ols) and symmetric di-aryl sulfides》. The information in the text is summarized as follows:

In this work, the surface of mesoporous MCM-41 was modified with guanidine, and then, Nickel particles have become immobilized on its surface (Ni-guanidine@MCM-41NPs). This heterogeneous catalyst has been identified by various techniques including: low-angle X-ray diffraction, SEM, energy-dispersive X-ray spectroscopy, inductively coupled plasma, thermal gravimetric anal. and N2 adsorption-desorption measurement isotherms, and its catalytic application was studied in the synthesis of 4,4′-(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ol) derivatives and sym. di-aryl sulfides. The prepared organometallic complex could be isolated, post-reaction, by simple filtration for several consecutive cycles without a notable change in its catalytic activity. After reading the article, we found that the author used o-Bromobenzaldehyde(cas: 6630-33-7HPLC of Formula: 6630-33-7)

o-Bromobenzaldehyde(cas: 6630-33-7) is used in L-threonine aldolase-catalyzed enantio/diastereoselective aldol reactions.HPLC of Formula: 6630-33-7Synthetic applications of o-Bromobenzaldehyde include: synthesis of aza-fused polycyclic quinolines through copper-catalyzed cascade reaction, preparation of 1-substituted indazoles by CuI-catalyzed coupling with N-aryl hydrazides.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Application of 583-69-7On October 20, 2021 ,《A Molecular Replication Process Drives Supramolecular Polymerization》 was published in Journal of the American Chemical Society. The article was written by Feng, Yuanning; Philp, Douglas. The article contains the following contents:

Supramol. polymers are materials in which the connections between monomers in the polymer main chain are non-covalent bonds. This area has seen rapid expansion in the last two decades and has been exploited in several applications. However, suitable contiguous hydrogen-bond arrays can be difficult to synthesize, placing some limitations on the deployment of supramol. polymers. We have designed a hydrogen-bonded polymer assembled from a bifunctional monomer composed of two replicating templates separated by a rigid spacer. This design allows the autocatalytic formation of the polymer main chain through the self-templating properties of the replicators and drives the synthesis of the bifunctional monomer from its constituent components in solution The template-directed 1,3-dipolar cycloaddition reaction between nitrone and maleimide proceeds with high diastereoselectivity, affording the bifunctional monomer. The high binding affinity between the self-complementary replicating templates that allows the bifunctional monomer to polymerize in solution is derived from the pos. cooperativity associated with this binding process. The assembly of the polymer in solution has been investigated by diffusion-ordered NMR spectroscopy. Both microcrystalline and thin films of the polymeric material can be prepared readily and have been characterized by powder X-ray diffraction and SEM. These results demonstrate that the approach described here is a valid one for the construction of supramol. polymers and can be extended to systems where the rigid spacer between the replicating templates is replaced by one carrying addnl. function. After reading the article, we found that the author used 2-Bromobenzene-1,4-diol(cas: 583-69-7Application of 583-69-7)

2-Bromobenzene-1,4-diol(cas: 583-69-7) belongs to organobromine compounds.Depending on the type of carbon to which the bromine is bonded, organic bromide could be alkyl, alkenyl, alkynyl, or aryl. Application of 583-69-7 Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Formula: C4H6BrFO2On September 4, 2019 ,《Three-Component Ruthenium-Catalyzed Direct Meta-Selective C-H Activation of Arenes: A New Approach to the Alkylarylation of Alkenes》 was published in Journal of the American Chemical Society. The article was written by Wang, Xin-Gang; Li, Yuke; Liu, Hong-Chao; Zhang, Bo-Sheng; Gou, Xue-Ya; Wang, Qiang; Ma, Jun-Wei; Liang, Yong-Min. The article contains the following contents:

Multicomponent reactions are fundamentally different from two-component reactions, as multicomponent reactions can enable the efficient and step-economical construction of complex mol. scaffolds from simple precursors. Here, an unprecedented three-component direct C-H addition was achieved in the challenging meta-selective fashion. Fluoroalkyl halides and a wide range of alkenes, including vinylarenes, unactivated alkenes, and internal alkenes, were employed as the coupling partners of arenes in this strategy. The detailed mechanism presented is supported by kinetic isotope studies, radical clock experiments, and d. functional theory calculations Moreover, this strategy provided access to various fluoride-containing bioactive 1,1-diarylalkanes and other challenging synthetically potential products. In addition to this study using Ethylbromofluoroacetate, there are many other studies that have used Ethylbromofluoroacetate(cas: 401-55-8Formula: C4H6BrFO2) was used in this study.

Ethylbromofluoroacetate(cas: 401-55-8) is a member of organofluorine compounds. Organofluorine compounds, which have carbon-fluorine bonds, show unique features such as high thermal and chemical stability, high surface activity, no light-absorbing ability, high pharmacological effect, and so on. Owing to their specific characters, they are indispensable chemicals for industry and our daily lives.Formula: C4H6BrFO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Catalytic Boration of Alkyl Halides with Borane without Hydrodehalogenation Enabled by Titanium Catalyst》 was written by Wang, Xianjin; Cui, Penglei; Xia, Chungu; Wu, Lipeng. HPLC of Formula: 7051-34-5This research focused ontitanium catalyzed boration alkyl pseudohalide borane radical pathway; alkyl boronate ester preparation; alkyl halides; boration; boronate ester; pinacolborane; titanium. The article conveys some information:

An unprecedented and general Ti-catalyzed boration of alkyl (pseudo)halides (alkyl-X, X = I, Br, Cl, OMs) with borane (HBpin, HBcat) is reported. The use of Ti catalyst can successfully suppress the undesired hydrodehalogenation products that prevail using other transition-metal catalysts. Synthetically useful alkyl boronate esters are readily obtained from various (primary, secondary, and tertiary) alkyl electrophiles, including unactivated alkyl chlorides, with tolerance of other reducing functional groups such as ester, alkene, and carbamate. Preliminary studies on the mechanism revealed a possible radical reaction pathway. Further extension of the authors’ strategy to aryl bromides is also demonstrated. The experimental part of the paper was very detailed, including the reaction process of (Bromomethyl)cyclopropane(cas: 7051-34-5HPLC of Formula: 7051-34-5)

(Bromomethyl)cyclopropane(cas: 7051-34-5) is used as a synthetic building block for the introduction of the cyclopropylmethyl group. It was also used in the synthesis of 1,4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents.HPLC of Formula: 7051-34-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Application In Synthesis of 4-Bromobutanoic acidIn 2021 ,《Targeted Delivery of mRNA with One-Component Ionizable Amphiphilic Janus Dendrimers》 was published in Journal of the American Chemical Society. The article was written by Zhang, Dapeng; Atochina-Vasserman, Elena N.; Maurya, Devendra S.; Liu, Matthew; Xiao, Qi; Lu, Juncheng; Lauri, George; Ona, Nathan; Reagan, Erin K.; Ni, Houping; Weissman, Drew; Percec, Virgil. The article contains the following contents:

Targeted and efficient delivery of nucleic acids with viral and synthetic vectors is the key step of genetic nanomedicine. The four-component lipid nanoparticle synthetic delivery systems consisting of ionizable lipids, phospholipids, cholesterol, and a PEG-conjugated lipid, assembled by microfluidic or T-tube technol., have been extraordinarily successful for delivery of mRNA to provide Covid-19 vaccines. Recently, we reported a one-component multifunctional sequence-defined ionizable amphiphilic Janus dendrimer (IAJD) synthetic delivery system for mRNA relying on amphiphilic Janus dendrimers and glycodendrimers developed in our laboratory Amphiphilic Janus dendrimers consist of functional hydrophilic dendrons conjugated to hydrophobic dendrons. Co-assembly of IAJDs with mRNA into dendrimersome nanoparticles (DNPs) occurs by simple injection in acetate buffer, rather than by microfluidic devices, and provides a very efficient system for delivery of mRNA to lung. Here we report the replacement of most of the hydrophilic fragment of the dendron from IAJDs, maintaining only its ionizable amine, while changing its interconnecting group to the hydrophobic dendron from amide to ester. The resulting IAJDs demonstrated that protonated ionizable amines play dual roles of hydrophilic fragment and binding ligand for mRNA, changing delivery from lung to spleen and/or liver. Replacing the interconnecting ester with the amide switched the delivery back to lung. Delivery predominantly to liver is favored by pairs of odd and even alkyl groups in the hydrophobic dendron. This simple structural change transformed the targeted delivery of mRNA mediated with IAJDs, from lung to liver and spleen, and expands the utility of DNPs from therapeutics to vaccines. The results came from multiple reactions, including the reaction of 4-Bromobutanoic acid(cas: 2623-87-2Application In Synthesis of 4-Bromobutanoic acid)

4-Bromobutanoic acid(cas: 2623-87-2) belongs to carboxylic acids. The chief chemical characteristic of the carboxylic acids is their acidity. They are generally more acidic than other organic compounds containing hydroxyl groups but are generally weaker than the familiar mineral acids (e.g., hydrochloric acid, HCl, sulfuric acid, H2SO4, etc.).Application In Synthesis of 4-Bromobutanoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of C7H5BrOIn 2019 ,《A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines》 was published in Journal of the American Chemical Society. The article was written by Ni, Shengyang; Padial, Natalia M.; Kingston, Cian; Vantourout, Julien C.; Schmitt, Daniel C.; Edwards, Jacob T.; Kruszyk, Monika M.; Merchant, Rohan R.; Mykhailiuk, Pavel K.; Sanchez, Brittany B.; Yang, Shouliang; Perry, Matthew A.; Gallego, Gary M.; Mousseau, James J.; Collins, Michael R.; Cherney, Robert J.; Lebed, Pavlo S.; Chen, Jason S.; Qin, Tian; Baran, Phil S.. The article contains the following contents:

Historically accessed through two-electron, anionic chem., ketones, alcs., and amines are of foundational importance to the practice of organic synthesis. After placing this work in proper historical context, this Article reports the development, full scope, and a mechanistic picture for a strikingly different way of forging such functional groups. Thus, carboxylic acids, once converted to redox-active esters (RAEs), can be utilized as formally nucleophilic coupling partners with other carboxylic derivatives (to produce ketones), imines (to produce benzylic amines), or aldehydes (to produce alcs.). The reactions are uniformly mild, operationally simple, and, in the case of ketone synthesis, broad in scope (including several applications to the simplification of synthetic problems and to parallel synthesis). Finally, an extensive mechanistic study of the ketone synthesis is performed to trace the elementary steps of the catalytic cycle and provide the end-user with a clear and understandable rationale for the selectivity, role of additives, and underlying driving forces involved. The experimental process involved the reaction of o-Bromobenzaldehyde(cas: 6630-33-7Electric Literature of C7H5BrO)

o-Bromobenzaldehyde(cas: 6630-33-7) is used in L-threonine aldolase-catalyzed enantio/diastereoselective aldol reactions.Electric Literature of C7H5BrOIt is also used in L-threonine aldolase-catalyzed enantio and diastereoselective aldol reactions. Further, it reacts with trichloromethane to prepare 1-(2-bromo-phenyl)-2,2,2-trichloro-ethanol.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary