Tag: 100-200

《BF3·OEt2-promoted tandem Meinwald rearrangement and nucleophilic substitution of oxiranecarbonitriles》 was published in Organic & Biomolecular Chemistry in 2020. These research results belong to Xu, Chuangchuang; Xu, Jiaxi. Application In Synthesis of o-Bromobenzaldehyde The article mentions the following:

Tandem Meinwald rearrangement and nucleophilic substitution of oxiranenitriles was realized. Arylacetic acid derivatives were readily synthesized from 3-aryloxirane-2-carbonitriles with amines, alcs., or water in the presence of boron trifluoride under microwave irradiation, and the designed synthetic strategy includes introducing a cyano leaving group into arylepoxides and capturing the in-situ generated toxic cyanide with boron trifluoride, making the reaction efficient, safe and environmentally benign. The reaction occurred through an acid-promoted Meinwald rearrangement, producing arylacetyl cyanides, followed by an addition-elimination process with nitrogen or oxygen-containing nucleophilic amines, alcs. or water. The current method provided a new application of the tandem Meinwald rearrangement. In the part of experimental materials, we found many familiar compounds, such as o-Bromobenzaldehyde(cas: 6630-33-7Application In Synthesis of o-Bromobenzaldehyde)

o-Bromobenzaldehyde(cas: 6630-33-7) is used in L-threonine aldolase-catalyzed enantio/diastereoselective aldol reactions.Application In Synthesis of o-BromobenzaldehydeSynthetic 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

《Synthesis of 3,4-dihydropyrimidin-2(1H)-one via retro-Biginelli reaction》 was published in Journal of Heterocyclic Chemistry in 2020. These research results belong to Mondal, Sudipta; Mondal, Mohabul A.. Quality Control of o-Bromobenzaldehyde The article mentions the following:

Hydrolytic behavior of 5-acetyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-ones under alk. condition had been explored. Mechanistic details were established by LCMS and HPLC. Evidence suggested that the deacetylative benzylidenation proceeded through the retro-Biginelli reaction. The scope of the retro-Biginelli reaction had been explored by the synthesis of substituted DHPs I [Ar = Ph, 4-MeC6H4, 2-BrC6H4; Ar1 = Ph, 4-MeC6H4, 2-BrC6H4, 3-MeOC6H4]. In the experimental materials used by the author, we found o-Bromobenzaldehyde(cas: 6630-33-7Quality Control of o-Bromobenzaldehyde)

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Reference of o-BromobenzaldehydeIn 2019 ,《A Microwave Accelerated Sustainable Approach for the Synthesis of 2-amino-4H-chromenes Catalyzed by WEPPA: A Green Strategy》 appeared in Current Microwave Chemistry. The author of the article were Hiremath, Prashant B.; Kamanna, Kantharaju. The article conveys some information:

We established an efficient, simple, agro-waste based catalytic approach for the synthesis of 2-amino-4H-chromene derivatives I [R1 = H, 2-Cl, 4-MeO, etc.], II [ R2 = H, 4-Me, 2-Cl, 4-Cl, 4-MeO] and III [R3 = H, 4-OH, 3-NO2, etc.] from the condensation of arylaldehyde, malononitrile and resorcinol/α-naphthol/β-naphthol employing WEPPA as an efficient catalyst under microwave synthesis. The method was found to be a greener, economic and eco-friendly approach for the synthesis of chromene scaffolds. The advantages of the present approach were solvent-free, no external metal, chem. base free, short reaction time and isolated product in good to excellent yields. The catalyst was agro-waste derived, which has abundant natural sources available, thus making the present approach a greener one. After reading the article, we found that the author used o-Bromobenzaldehyde(cas: 6630-33-7Reference of o-Bromobenzaldehyde)

o-Bromobenzaldehyde(cas: 6630-33-7) is used in L-threonine aldolase-catalyzed enantio/diastereoselective aldol reactions.Reference of o-BromobenzaldehydeIt 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

In 2022,Ruhland, Klaus; Horny, Robert; Wanzel, Andrea; Reisach, Sebastian; Nizamutdinova, Alina; Kirchhain, Holger; Rehfuss, Ulrich; van Wuellen, Leo; Fischer, Andreas; Scheliga, Felix; Huebner, Tobias published an article in Journal of Applied Polymer Science. The title of the article was 《Investigation of the chemical changes during the thermal treatment of acrylonitrile -co- methyl acrylate-polymer (polyacrylonitrile-precursor) focusing on the fate of the methyl acrylate moiety》.Category: bromides-buliding-blocks The author mentioned the following in the article:

Seventeen samples of acrylonitrile (AN)-co-Me acrylate (MA)-polymer (MA content 0-11 mol%) are examined Several selective isotopic labelings are employed (d1-MA, d2-MA, 13CO-MA, CD3-MA, d1-AN, d2-AN, and 15N-AN). The thermal treatment under inert atm. is investigated to gain insight into the chem. transformation mechanisms concerning the MA sub-unit. The volatiles are determined by means of evolved gas anal. (EGA) (Fourier transform IR [FTIR] and GC/MS). Methanol is found for the first time as one decisive volatile stemming from the MA sub-unit, next to water and carbon dioxide. In addition, methylamines are proven to be formed by reaction of ammonia with the MA sub-unit, while a similar reaction of hydrogen cyanide (HCN) yielding in acetonitrile could be ruled out. Several volatile compounds could even be quantified. The non-volatile polymeric material is characterized by means of simultaneous thermal anal. (differential scanning calorimetry, thermogravimetric anal.), in-situ-FTIR spectroscopy and sophisticated solid-state NMR methods. Selected defined model compounds are synthesized and analyzed for comparison. Detailed reaction mechanisms for the thermal transformation are concluded from the results, pointing in particular to the importance of ammonia for all processes as stoichiometric and/or catalytic reagent. In the experiment, the researchers used many compounds, for example, Methyl 3-bromopropanoate(cas: 3395-91-3Category: bromides-buliding-blocks)

Methyl 3-bromopropanoate(cas: 3395-91-3) belongs to bromides. 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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2022,Liu, Yulin; Uras, Giuseppe; Onuwaje, Itse; Li, Wenlong; Yao, Hong; Xu, Shengtao; Li, Xinuo; Li, Xinnan; Phillips, James; Allen, Stephanie; Gong, Qi; Zhang, Haiyan; Zhu, Zheying; Liu, Jie; Xu, Jinyi published an article in European Journal of Medicinal Chemistry. The title of the article was 《Novel inhibitors of AChE and Aβ aggregation with neuroprotective properties as lead compounds for the treatment of Alzheimer’s disease》.Recommanded Product: Ethyl 3-bromopropanoate The author mentioned the following in the article:

A series of sulfone analogs of donepezil I (R1 = H, F; R2 = H, 4-F, 3-Cl, etc.) were designed and synthesized as novel acetylcholinesterase (AChE) inhibitors with the potent inhibiting Aβ aggregation and providing neuroprotective effects as potential modalities for Alzheimer’s disease (AD). Most of the target compounds displayed effective inhibition of AChE, especially compound II which displayed powerful inhibitory activity (IC50 = 2.4 nM). Kinetic and docking studies indicated that compound II was a mixed-type inhibitor. Furthermore, in glyceraldehyde (GA)-exposed SH-SY5Y differentiated neuronal cells, compound II could potently inhibit AChE, reduce tau phosphorylation at S396 residue, provide neuroprotection by rescuing neuronal morphol. and increasing cell viability. It was also found to reduce amyloid aggregation in the presence of AChE. In addition, compound II showed evident protections from mitochondrial membrane dysfunction and oxidative stress in okadaic acid-induced pharmacol. models. Moreover, compound II exhibited more effective treatment prospects in vivo than donepezil, including a moderate blood-brain barrier permeability, a more potent AChE inhibitory activity and behavioral improvement in scopolamine-induced cognition-impaired mice model at a much lower dose. Collectively, compound II is a promising lead compound for further investigation to discovery and development of new anti-AD agents. The experimental process involved the reaction of Ethyl 3-bromopropanoate(cas: 539-74-2Recommanded Product: Ethyl 3-bromopropanoate)

Ethyl 3-bromopropanoate(cas: 539-74-2) 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. Recommanded Product: Ethyl 3-bromopropanoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2022,Schwickert, Marvin; Fischer, Tim R.; Zimmermann, Robert A.; Hoba, Sabrina N.; Meidner, J. Laurenz; Weber, Marlies; Weber, Moritz; Stark, Martin M.; Koch, Jonas; Jung, Nathalie; Kersten, Christian; Windbergs, Maike; Lyko, Frank; Helm, Mark; Schirmeister, Tanja published an article in Journal of Medicinal Chemistry. The title of the article was 《Discovery of Inhibitors of DNA Methyltransferase 2, an Epitranscriptomic Modulator and Potential Target for Cancer Treatment》.COA of Formula: C4H7BrO2 The author mentioned the following in the article:

Selective manipulation of the epitranscriptome could be beneficial for the treatment of cancer and also broaden the understanding of epigenetic inheritance. Inhibitors of the tRNA methyltransferase DNMT2, the enzyme catalyzing the S-adenosylmethionine-dependent methylation of cytidine 38 to 5-methylcytidine, were designed, synthesized, and analyzed for their enzyme-binding and -inhibiting properties. For rapid screening of potential DNMT2 binders, a microscale thermophoresis assay was established. Besides the natural inhibitors S-adenosyl-L-homocysteine (SAH) and sinefungin (SFG), we identified new synthetic inhibitors based on the structure of N-adenosyl-2,4-diaminobutyric acid (Dab). Structure-activity relationship studies revealed the amino acid side chain and a Y-shaped substitution pattern at the 4-position of Dab as crucial for DNMT2 inhibition. The most potent inhibitors are alkyne-substituted derivatives, exhibiting similar binding and inhibitory potencies as the natural compounds SAH and SFG. CaCo-2 assays revealed that poor membrane permeabilities of the acids and rapid hydrolysis of an ethylester prodrug might be the reasons for the insufficient activity in cellulo. The experimental process involved the reaction of 4-Bromobutanoic acid(cas: 2623-87-2COA of Formula: C4H7BrO2)

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.).COA of Formula: C4H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tan, Fei; Pu, Maoping; He, Jun; Li, Jinzhao; Yang, Jian; Dong, Shunxi; Liu, Xiaohua; Wu, Yun-Dong; Feng, Xiaoming published an article in 2021. The article was titled 《Catalytic Asymmetric Homologation of Ketones with α-Alkyl α-Diazo Esters》, and you may find the article in Journal of the American Chemical Society.Application of 3395-91-3 The information in the text is summarized as follows:

The homologation of ketones with diazo compounds was a useful strategy to synthesize one-carbon chain-extended acyclic such as PhC(O)CMeCO2MeR [R = allyl, Bn, CH2(2-naphthyl), etc.] or ring-expanded cyclic ketones e.g., I. However, the asym. homologation of acyclic ketones with α-diazo esters remains a challenge due to the lower reactivity and complicated selectivity. Herein, the enantioselective catalytic homologation of acetophenone and related derivatives with α-alkyl α-diazo esters was reported utilizing a chiral scandium(III) N,N’-dioxide as the Lewis acid catalyst. This reaction supplies a highly chemo-, regio-, and enantioselective pathway for the synthesis of optically active β-keto esters with an all-carbon quaternary center through highly selective alkyl-group migration of the ketones. Moreover, the ring expansion of cyclic ketones was accomplished under slightly modified conditions, affording a series of enantioenriched cyclic β-keto esters. D. functional theory calculations was carried out to elucidate the reaction pathway and possible working models that could explain the observed regio- and enantioselectivity. The experimental process involved the reaction of Methyl 3-bromopropanoate(cas: 3395-91-3Application of 3395-91-3)

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.Application of 3395-91-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2017,Zou, Ya-Ling; Wang, Zhen-Yu; Feng, Yin-Mao; Li, You-Gui; Kantchev, Eric Assen B. published 《Solvent and Base in One: Tetra-n-butylammonium Acetate as a Multi-Purpose Ionic Liquid Medium for Ru-Catalyzed Directed Mono- and Di-o-C-H Arylation Reactions》.European Journal of Organic Chemistry published the findings.Safety of 1-Bromo-2-isopropylbenzene The information in the text is summarized as follows:

Ru-catalyzed directed o-C-H arylation reactions of 2-phenylpyridine, N-phenylpyrazole, acetophenone N-(p-methoxyphenyl)imine, and 2-phenyloxazoline proceed in good to excellent yields with a number of functionalized aryl and heteroaryl bromides in neat Bu4NOAc at 120°. The acetate ion acts as the base and the relatively low m.p. Bu4N salts (a mixture of acetate and bromide) behave as an ionic liquid Arylation reactions of 2-phenyloxazoline proceed with concomitant oxazolidine cleavage to give 2-(N-acetylamino)ethyl benzoates promoted by side product CH3COOH. The dual-purpose ionic liquid medium is compatible with both ligandless Ru for di-arylation (optimal pre-catalyst: RuCl3·xH2O) and Ru-phosphine (optimal pre-catalyst: [RuCl2(p-cymene)]2/P(p-Tol)3 1:4) catalysts (1-5 mol-%) for selective mono-arylation. The experimental part of the paper was very detailed, including the reaction process of 1-Bromo-2-isopropylbenzene(cas: 7073-94-1Safety of 1-Bromo-2-isopropylbenzene)

1-Bromo-2-isopropylbenzene(cas: 7073-94-1) 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. Alkyl bromides are mainly used as alkylating agents and also find application as a solvent to extract oil from seeds and wool. Safety of 1-Bromo-2-isopropylbenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Radical Monofluoroalkylative Alkynylation of Olefins by a Docking-Migration Strategy》 were Wang, Min; Zhang, Huihui; Liu, Jige; Wu, Xinxin; Zhu, Chen. And the article was published in Angewandte Chemie, International Edition in 2019. SDS of cas: 401-55-8 The author mentioned the following in the article:

A radical-mediated monofluoroalkylative alkynylation of alkenes is disclosed for the first time. The reaction demonstrates a remarkably broad substrate scope in which both activated and unactivated alkenes are suitable starting materials. The concurrent addition of an alkynyl and a monofluoroalkyl group onto an alkene proceeds through a docking-migration sequence, affording a vast array of valuable fluoroalkyl-substituted alkynes. Many complex natural products and drug derivatives are readily functionalized, demonstrating that this method can be used for late-stage alkynylation. In the experimental materials used by the author, we found Ethylbromofluoroacetate(cas: 401-55-8SDS of cas: 401-55-8)

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.SDS of cas: 401-55-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Discovery of Novel 3,4-Dichloroisothiazole-Containing Coumarins as Fungicidal Leads》 was written by Lv, You; Liu, Hanlu; Wang, Lifan; Li, Kun; Gao, Wei; Liu, Xiaoyu; Tang, Liangfu; Kalinina, Tatiana A.; Glukhareva, Tatiana V.; Fan, Zhijin. COA of Formula: C4H6BrFO2 And the article was included in Journal of Agricultural and Food Chemistry on April 14 ,2021. The article conveys some information:

Natural products are one of the resources for discovering novel fungicidal leads. As a natural fungicide, osthole was used as a coumarin-based lead compound for the development of novel fungicides. Here, a series of 3,4-dichloroisothiazole-containing 7-hydroxycoumarins were rationally designed, synthesized, and characterized by introducing a bioactive substructure, 3,4-dichloroisothiazole, into the coumarin skeleton. In vitro bioassay indicated that compound (I) displayed good activity against Rhizoctonia solani, Physalospora piricola, Sclerotinia sclerotiorum, and Botrytis cinerea. Its median effective concentration (EC50) value against each of these fungi fell between 0.88 and 2.50μg/mL, which was much lower than that of osthole against the corresponding pathogen (between 7.38 and 74.59μg/mL). In vivo screening validated that (II) exhibited 100%, 60%, and 20% efficacy against R. solani at 200, 100, and 50μg/mL, resp. RNA sequence anal. implied that growth inhibition of R. solani by II might result from potential disruptions of fungal membrane formation and intracellular metabolism Furthermore, a field experiment with cucumber plants indicated that (III) showed 62.73% and 74.03% efficacy against Pseudoperonospora cubensis (Berk. & Curt.) Rostov. at rates of 12.5 g a.i./ha and 25 g a.i./ha, resp., which showed no significant difference between III and osthole at 30 g a.i./ha. Our studies suggested that III, I, and II might be used as fungicidal leads for further optimization. The experimental process involved the reaction of Ethylbromofluoroacetate(cas: 401-55-8COA of Formula: C4H6BrFO2)

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.COA of Formula: C4H6BrFO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary