Tag: 200-300

Battistuzzi, Gianfranco; Cacchi, Sandro; Fabrizi, Giancarlo; Bernini, Roberta published an article in Synlett. The title of the article was 《3-Arylpropanoate esters through the palladium-catalyzed reaction of aryl halides with acrolein diethyl acetal》.Category: bromides-buliding-blocks The author mentioned the following in the article:

The reaction of aryl halides with acrolein di-Et acetal in the presence of Pd(OAc)2, n-Bu3N, and n-Bu4NCl in DMF at 90° affords Et 3-arylpropanoates. A variety of functional groups are tolerated in the aryl halides, including ether, aldehyde, ketone, ester, nitrile, and nitro groups. Ortho-substituents do not hamper the reaction. 3-Arylpropanoate esters were isolated in good to excellent yields with many neutral, electron-rich and electron-poor aryl iodides and electron-poor aryl bromide. Neutral and electron-rich aryl bromides gave the desired ester in moderate yields. After reading the article, we found that the author used Ethyl 3-(2-bromophenyl)propanoate(cas: 135613-33-1Category: bromides-buliding-blocks)

Ethyl 3-(2-bromophenyl)propanoate(cas: 135613-33-1) belongs to organobromine compounds.The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of C6H4BBrF3KOn May 1, 2020 ,《Deacetylative Aryl Migration of Diaryliodonium Salts with C(sp2)-N Bond Formation toward ortho-Iodo N-Aryl Sulfonamides》 appeared in Organic Letters. The author of the article were Chen, Huangguan; Wang, Limin; Han, Jianwei. The article conveys some information:

An unprecedented approach of metal-free C(sp2)-N bond formation via deacetylation/intramol. aryl migration is demonstrated with novel N-sulfonamide substituted diaryliodonium salts. The reaction provides a variety of ortho-iodo N-aryl sulfonamides. The products were employed in several coupling reactions to afford useful diarylamine scaffolds. Furthermore, the key intermediates of zwitterionic iodoniums in the reaction were isolated and verified by the X-ray crystallog. anal., which showcased unambiguous mechanistic insight into the reactivity of the reaction cascade. In the experiment, the researchers used many compounds, for example, potassium (3-bromophenyl)trifluoroborate(cas: 374564-34-8Electric Literature of C6H4BBrF3K)

potassium (3-bromophenyl)trifluoroborate(cas: 374564-34-8) belongs to organobromine compounds.The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. Electric Literature of C6H4BBrF3K 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

《Development of pyrazolo[3,4-d]pyrimidine-6-amine-based TRAP1 inhibitors that demonstrate in vivo anticancer activity in mouse xenograft models》 was written by Kim, Darong; Kim, So-Yeon; Kim, Dongyoung; Yoon, Nam Gu; Yun, Jisu; Hong, Ki Bum; Lee, Changwook; Lee, Ji Hoon; Kang, Byoung Heon; Kang, Soosung. Quality Control of 4-Bromo-1-(bromomethyl)-2-fluorobenzene And the article was included in Bioorganic Chemistry on August 31 ,2020. The article conveys some information:

TNF Receptor Associated Protein 1 (TRAP1) is a mitochondrial paralog of Hsp90 related to the promotion of tumorigenesis in various cancers via maintaining mitochondrial integrity, reducing the production of reactive oxygen species, and reprogramming cellular metabolism Consequently, Hsp90 and TRAP1 have been targeted to develop cancer therapeutics. Herein, we report a series of pyrazolo[3,4-d]pyrimidine derivatives that are mitochondria-permeable TRAP1 inhibitors. Structure-based drug design guided the optimization of potency, leading to the identification of compounds 47 and 48 as potent TRAP1 and Hsp90 inhibitors with good metabolic and plasma stability as well as acceptable CYP and hERG inhibition. X-ray co-crystallization studies confirmed both 47 and 48 interact with the ATP binding pocket in the TRAP1 protein. Compounds 47 and 48 demonstrated excellent anticancer efficiency in various cancer cells, with limited toxicity over normal hepatocyte and prostate cells. Mouse PC3 xenograft studies showed 47 and 48 significantly reduced tumor growth. The experimental process involved the reaction of 4-Bromo-1-(bromomethyl)-2-fluorobenzene(cas: 76283-09-5Quality Control of 4-Bromo-1-(bromomethyl)-2-fluorobenzene)

4-Bromo-1-(bromomethyl)-2-fluorobenzene(cas: 76283-09-5) belongs to organobromine compounds.Organobromine chemicals are produced naturally by an array of biological and other chemical processes in our environment. Organobromine compounds are produced naturally by marine creatures (sponges, corals, sea slugs, tunicates, sea fans) and seaweed, plants, fungi, lichen, algae, bacteria, microbes, and some mammals. Quality Control of 4-Bromo-1-(bromomethyl)-2-fluorobenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Development of an efficient and sustainable synthesis of 2-(3-methyl-1H-1,2,4-triazol-1-yl)acetic acid under continuous-flow conditions》 was written by Tortoioli, Simone; Friedli, Astrid; Prud’homme, Alice; Richard-Bildstein, Sylvia; Kohler, Philipp; Abele, Stefan; Vile, Gianvito. Related Products of 5437-45-6This research focused ontriazole preparation green chem continuous flow. The article conveys some information:

A novel, metal-free process for the challenging synthesis of 2-(3-methyl-1H-1,2,4-triazol-1-yl)acetic acid is reported, which features an efficient construction of the triazole ring under flow conditions. This continuous, one-pot method is atom economical, highly selective and environmentally benign, due to the avoidance of chromatog. and isolation steps. Compared to the earlier batch routes, higher yields were achieved in a flow reactor. In addition, a highly-energetic intermediate could be controlled and handled in a safe manner. To generalize the established route, several triazoles I (R = CH2CO2Et, CH2CO2CH2C6H5, 4-FC6H4, CH2C6H5, 4-OCH3C6H4CH2, cyclohexyl; R1 = H, 5-bromopyridin-3-yl) were prepared under the described conditions, confirming that the methodol. could find useful applications for the rapid and sustainable construction of differentially-functionalized 1,2,4-triazoles.Benzyl 2-bromoacetate(cas: 5437-45-6Related Products of 5437-45-6) was used in this study.

Benzyl 2-bromoacetate(cas: 5437-45-6) has been used in the alkylation of (-)-2,3-O-isopropylidene-D-threitol that afforded lipopeptide, 2-[(4R,5R)-5-({[(9H-fluoren-9-yl)methoxy]carbonylaminomethyl}-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]acetic acid.Related Products of 5437-45-6

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Safety of Bromopentacarbonylmanganese(I)In 2020 ,《Selective reductive cross-coupling of N-heteroarenes by an unsymmetrical PNP-ligated manganese catalyst》 was published in Journal of Catalysis. The article was written by Tan, Zhenda; Xiong, Biao; Yang, Jian; Ci, Chenggang; Jiang, Huanfeng; Zhang, Min. The article contains the following contents:

Herein, by developing an unprecedented manganese catalyst ligating with an unsym. 2-aminotetrahydronaphthyridyl PNP-ligands e.g., I, a new reductive cross-coupling of indoles II (R = H, 5-MeO, 7-Me, 2,5-di-Me, etc.)/1H-pyrrole, 2,5-dimethyl-1H-pyrrole and N-heteroarenes III (R1 = H, 2,3-di-Me, 4-chlorophenyl, thiophen-2-yl, etc.; X = CH, N) was achieved. Mechanistic investigations show that the catalyst-enabled in situ capture of the partially reduced intermediates by interruption of the second transfer hydrogenation of N-heteroarenes constitutes the key to success for the present reaction. The developed chem. proceeds with good substrate and functional group compatibility, high step and atom efficiency, and excellent chemo and regioselectivity, and is applicable for late-stage modification of pyridine-containing biomedical mols., which has established a new platform allowing the linkage of aromatic systems into functional frameworks, and further development of unsym. PNP organometallic complexes and related catalytic transformations. In the experiment, the researchers used many compounds, for example, Bromopentacarbonylmanganese(I)(cas: 14516-54-2Safety of Bromopentacarbonylmanganese(I))

Bromopentacarbonylmanganese(I)(cas: 14516-54-2) has many other uses. It is used in the formation of (eta6-arene)tricarbonylmanganese(I) by reacting with arene (arene= hexamethyl benzene, 1,2,4,5-tetramethyl benzene, mesitylene, p-xylene and toluene) in the presence silver salt.Safety of Bromopentacarbonylmanganese(I)

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Name: 4-Bromobenzoic acidIn 2020 ,《Accelerated Reactivity Mechanism and Interpretable Machine Learning Model of N-Sulfonylimines toward Fast Multicomponent Reactions》 was published in Organic Letters. The article was written by Jethava, Krupal P.; Fine, Jonathan; Chen, Yingqi; Hossain, Ahad; Chopra, Gaurav. The article contains the following contents:

We introduce chem. reactivity flowcharts to help chemists interpret reaction outcomes using statistically robust machine learning models trained on a small number of reactions. We developed fast N-sulfonylimine multicomponent reactions for understanding reactivity and to generate training data. Accelerated reactivity mechanisms were investigated using d. functional theory. Intuitive chem. features learned by the model accurately predicted heterogeneous reactivity of N-sulfonylimine with different carboxylic acids. Validation of the predictions shows that reaction outcome interpretation is useful for human chemists. The experimental part of the paper was very detailed, including the reaction process of 4-Bromobenzoic acid(cas: 586-76-5Name: 4-Bromobenzoic acid)

4-Bromobenzoic acid(cas: 586-76-5) has been used to study the metabolic fate of 2-,3-and 4-bromo benzoic acids in rat hepatocytes incubation using high temperature liquid chromatography. It was used in bromine-specific detection of the metabolites of 2-,3-and 4-bromobenzoic acid in the urine and bile of rats by inductively coupled plasma mass spectrometry.Name: 4-Bromobenzoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Functional Janus dendrimers containing carbazole with liquid crystalline, optical and electrochemical properties》 was written by Iguarbe, Veronica; Barbera, Joaquin; Serrano, Jose Luis. Computed Properties of C7H13BrO2 And the article was included in Liquid Crystals in 2020. The article conveys some information:

Novel liquid crystalline Janus dendrimers that combine a mesogenic block and an electroactive block have been synthesized. The mesogenic block is based on two third-generation Percec-type dendrons bearing six or eight terminal dodecyloxy alkyl chains, whereas the electroactive blocks are formed by one or two carbazole units. The liquid crystal behavior was investigated by polarized-light optical microscopy, differential scanning microscopy and X-ray diffraction. The Janus dendrimers with one electroactive unit exhibited cubic or columnar liquid crystal phases, whereas the Janus dendrimers with two electroactive units did not show liquid crystalline behavior. The UV-vis absorption and emission properties of the Janus dendrimers were investigated. The spectra suggested the existence of π-π stacking and the formation of aggregates in the solid state. Electrodeposition of the carbazole-containing dendrimers afforded semi-globular particles in which the number of electropolymerizable units and the flexible or rigid character of the linker have a decisive influence in the particle size. In the experiment, the researchers used many compounds, for example, Ethyl 5-bromovalerate(cas: 14660-52-7Computed Properties of C7H13BrO2)

Ethyl 5-bromovalerate(cas: 14660-52-7) 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.Computed Properties of C7H13BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Optimization of the benzamide fragment targeting the S2′ site leads to potent dipeptidyl peptidase-IV inhibitors》 was published in Bioorganic Chemistry in 2020. These research results belong to Deng, Xiaoyan; Wang, Na; Meng, Liuwei; Zhou, Siru; Huang, Junli; Xing, Junhao; He, Linhong; Jiang, Weizhe; Li, Qing. SDS of cas: 1129-28-8 The article mentions the following:

Our recently successful identification of benzoic acid-based DPP-4 inhibitors spurs the further quest for in-depth structure-activity relationships (SAR) study in S2′ site DPP-4. Thus novel benzamide fragments were designed to target the S2′ site to compromise lipophilicity and improve oral activity. Exploring SAR by introduction of a variety of amide and halogen on benzene ring led to identification of several compounds, exerting moderated to excellent DPP-4 activities, in which 4′-chlorine substituted Me amide, (R)-3-((4-(3-aminopiperidin-1-yl)-3-(but-2-yn-1-yl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl)-4-chloro-N-methylbenzamide hydro chloride (17g), [2380226-71-9], showed most potent DPP-4 activity with the IC50 value of 1.6 nM. Its activity was superior to reference alogliptin. Docking study ideally verified and interpreted the obtained SAR of designed compounds As a continuation, DPP-8/9 assays revealed the designed compounds exhibited good selectivity over DPP-8 and DPP-9. Subsequent cell-based test indicated (17g) displayed low toxicity toward the LO2 cell line up to 100μM. In vivo evaluation showed (17g) robustly improved the glucose tolerance in normal mice. Importantly, (17g) exhibited reasonable pharmacokinetic (PK) profiles for oral delivery. Overall, (17g) has the potential to a safe and efficacious DPP-4 inhibitor for T2DM treatment. In the experimental materials used by the author, we found Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8SDS of cas: 1129-28-8)

Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8) 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. Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides. SDS of cas: 1129-28-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Access to Aryl and Heteroaryl Trifluoromethyl Ketones from Aryl Bromides and Fluorosulfates with Stoichiometric CO》 was published in Organic Letters in 2020. These research results belong to Johansen, Martin B.; Gedde, Oliver R.; Mayer, Thea S.; Skrydstrup, Troels. Safety of 4-Bromobenzoic acid The article mentions the following:

A sequential one-pot preparation of aromatic trifluoromethyl ketones RC(O)CF3 (R = 3,5-dimethoxyphenyl, quinolin-3-yl, 4-adamantylphenyl, etc.) starting from readily accessible aryl bromides/fluorosulfates RX (X = Br, OS(O)2F), the latter easily prepared from the corresponding phenols ROH were reported. The methodol. utilizes low pressure carbon monoxide generated ex situ from COgen to generate Weinreb amides as reactive intermediates that undergo monotrifluoromethylation affording the corresponding aromatic trifluoromethyl ketones (TFMKs) in good yields. The stoichiometric use of CO enables the possibility for accessing 13C-isotopically labeled TFMK by switching to the use of 13COgen. In the experiment, the researchers used 4-Bromobenzoic acid(cas: 586-76-5Safety of 4-Bromobenzoic acid)

4-Bromobenzoic acid(cas: 586-76-5) has been used in bromine-specific detection of the metabolites of 2-,3-and 4-bromobenzoic acid in the urine and bile of rats by inductively coupled plasma mass spectrometry.Safety of 4-Bromobenzoic acid It was used to study the metabolic fate of 2-,3-and 4-bromo benzoic acids in rat hepatocytes incubation using high temperature liquid chromatography.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Hydrosilylation of Esters Catalyzed by Bisphosphine Manganese(I) Complex: Selective Transformation of Esters to Alcohols》 was published in Organic Letters in 2020. These research results belong to Behera, Rakesh R.; Ghosh, Rahul; Panda, Surajit; Khamari, Subrat; Bagh, Bidraha. Safety of Bromopentacarbonylmanganese(I) The article mentions the following:

A tricarbonylruthenium Xantphos complex I was prepared and characterized by X-ray crystallog.; in the presence of I, esters underwent chemoselective hydrosilylation with phenylsilane under neat conditions (followed by workup with base) to yield esters. Aryl, alkyl, and alkenyl mono- and dicarboxylates and lactones underwent chemoselective reduction to alcs. and diols; ketoesters underwent reduction to diols. Poly(1,6-hexanediol adipate) underwent hydrosilylation to 1,6-hexanediol. The experimental process involved the reaction of Bromopentacarbonylmanganese(I)(cas: 14516-54-2Safety of Bromopentacarbonylmanganese(I))

Bromopentacarbonylmanganese(I)(cas: 14516-54-2) has many other uses. It is used in the formation of (eta6-arene)tricarbonylmanganese(I) by reacting with arene (arene= hexamethyl benzene, 1,2,4,5-tetramethyl benzene, mesitylene, p-xylene and toluene) in the presence silver salt.Safety of Bromopentacarbonylmanganese(I)

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary