Month: October 2022

Chalyk, Bohdan A.; Khutorianskyi, Andrii; Lysenko, Andrii; Fil, Yulia; Kuchkovska, Yuliya O.; Gavrilenko, Konstantin S.; Bakanovych, Iulia; Moroz, Yurii S.; Gorlova, Alina O.; Grygorenko, Oleksandr O. published their research in Journal of Organic Chemistry on December 6 ,2019. The article was titled 《Regioselective Synthesis of Functionalized 3- or 5-Fluoroalkyl Isoxazoles and Pyrazoles from Fluoroalkyl Ynones and Binucleophiles》.Application In Synthesis of Ethylbromofluoroacetate The article contains the following contents:

A facile synthetic route towards either 3- or 5-fluoroalkyl-substituted isoxazoles or pyrazoles containing an addnl. functionalization site was developed and applied on a multigram scale. The elaborated approach extends the scope of fluoroalkyl substituents for introduction into the heterocyclic moiety, and uses convenient transformations of the side chain for incorporation of fluoroalkyl substituted azoles into the structures of biol. active mols. The utility of the obtained building blocks for isosteric replacement of alkyl-substituted isoxazole and pyrazole was shown by the synthesis of fluorinated Isocarboxazid and Mepiprazole analogs. After reading the article, we found that the author used Ethylbromofluoroacetate(cas: 401-55-8Application In Synthesis of Ethylbromofluoroacetate)

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.Application In Synthesis of Ethylbromofluoroacetate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 1940,Journal of Organic Chemistry included an article by Burger, Alfred; Avakian, S.. Synthetic Route of C7H4BrNO4. The article was titled 《Some derivatives of homoanisic acid》. The information in the text is summarized as follows:

p-Homoanisic acid (I), m. 86-7°, is prepared in a yield of 53% according to Arndt and Eistert (C. A. 29, 3223.9) by treating 20 g. p-MeOC6H4COCHN2 in 100 cc. dioxane with 150 cc. concentrated NH4OH and 30 cc. 10% AgNO3 solution at 60-70°. The mixture is boiled for 2 h. and the filtered p-homoanisamide, m. 188-9°, is saponified with KOH and I is precipitated on acidification. When 16.6 g. I is added to 30 cc. HSO3Cl at -5°, the mixture kept below 0° for 1 h., then warmed to 40° and kept there for 5 min., 3-chlorosulfonylhomoanisic acid (II), m. 164-5°, crystallized from C6H6, is obtained in 80.6% yield. Reduction of II with Zn dust and H2SO4 gives 3-thio-p-homoanisic acid (III), m. 83-4°, in 83% yield. That chlorosulfonation has taken place in the 3-position is shown by its synthesis from 3-nitro-p-homoanisic acid (IV). IV, m. 132-3°, is prepared in 70% yield by saponification of 3-nitro-4-methoxybenzyl cyanide, m. 87-7.5°, obtained by interaction of MeO(O2N)C6H3CH2Cl and KCN in 45% yield, with 50% H2SO4 in AcOH. IV is also formed when 0.5 g. I is nitrated with 1 cc. concentrated HNO3 in 5 cc. AcOH at 0°. Reduction of IV in the presence of Raney Ni gives 3-aminohomoanisic acid (V), m. 110-11°, in 90% yield. Treatment of V with NaNO2 in H2SO4, at 0° gives homoisovanillic acid, m. 127-8°. Treatment of the diazo compound from 7.24 g. V with a solution prepared by dissolving 12.4 g. Na2S.9H2O and 1.3 g. powd. S in 12 cc. boiling H2O gives on acidification 3,3′-dithiohomoanisic acid, which on reduction with Zn dust in AcOH, gives III in 25% yield. Condensation of 1.24 g. III with 2.46 g. 2-nitro-3-bromobenzoic acid, m. 250-1°, prepared by oxidation of 2-nitro-3-bromotoluene with Cr2O3 in 70% yield, gives 2′-nitro-3′-carboxy-2-methoxydiphenyl sulfide-5-acetic acid (VI), m. 232-4° (decomposition), in 46% yield. Reduction of VI in NH4OH with Fe(OH)2 gives the 2′-amino derivative, m. 222-4°, in 66% yield. In the part of experimental materials, we found many familiar compounds, such as 3-Bromo-2-nitrobenzoic acid(cas: 116529-61-4Synthetic Route of C7H4BrNO4)

3-Bromo-2-nitrobenzoic acid(cas: 116529-61-4) 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. Synthetic Route of C7H4BrNO4 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

The author of 《Nucleophilic aromatic substitution reactions of unactivated aryl halides with thiolate ions in hexamethylphosphoramide》 were Cogolli, Pietro; Maiolo, Filippo; Testaferri, Lorenzo; Tingoli, Marco; Tiecco, Marcello. And the article was published in Journal of Organic Chemistry in 1979. Application In Synthesis of 1-Bromo-3-(isopropylsulfonyl)benzene The author mentioned the following in the article:

A simple, high-yields method for the synthesis of aryl thioethers via nucleophilic displacement of unactivated aryl halides by the sodium salts of thiols in hexamethylphosphoramide (HMPA) is reported. The reactions proceed by the bimol. displacement mechanism SNAr. Competitive experiments showed that the four halobenzenes presented comparable reactivities toward isopropanethiol anions; the relative halogen mobility was I > F > Br > Cl. The effect of some substituents on the reactivity of chlorobenzene were also measured.1-Bromo-3-(isopropylsulfonyl)benzene(cas: 70399-01-8Application In Synthesis of 1-Bromo-3-(isopropylsulfonyl)benzene) was used in this study.

1-Bromo-3-(isopropylsulfonyl)benzene(cas: 70399-01-8) 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. Application In Synthesis of 1-Bromo-3-(isopropylsulfonyl)benzene 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

The author of 《Temperature-controlled sequential Suzuki-Miyaura reactions for preparing unsymmetrical terphenyls》 were Li, Xinmin; Liu, Chun; Wang, Lei; Ye, Qing; Jin, Xin; Jin, Zilin. And the article was published in Organic & Biomolecular Chemistry in 2018. Quality Control of potassium (3-bromophenyl)trifluoroborate The author mentioned the following in the article:

A one-pot protocol of double Suzuki-Miyaura reactions was developed for the synthesis of unsym. teraryls. In the absence of a ligand, potassium bromophenyltrifluoroborate reacted with arylboronic acid and then sequentially with a hetero/aryl bromide by controlling the reaction temperature, providing unsym. p- and m-teraryl compounds in moderate to good overall yields. This protocol provided a convenient and practically approached to unsym. terphenyls under ligand-free and aerobic conditions.potassium (3-bromophenyl)trifluoroborate(cas: 374564-34-8Quality Control of potassium (3-bromophenyl)trifluoroborate) was used in this study.

potassium (3-bromophenyl)trifluoroborate(cas: 374564-34-8) 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. Due to the reactivity of bromide, they are used as potential precursors or important intermediates in organic synthesis. Quality Control of potassium (3-bromophenyl)trifluoroborate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2003,Gohier, Frederic; Mortier, Jacques published 《ortho-Metalation of Unprotected 3-Bromo and 3-Chlorobenzoic Acids with Hindered Lithium Dialkylamides》.Journal of Organic Chemistry published the findings.Name: 3-Bromo-2-methylbenzoic acid The information in the text is summarized as follows:

Upon treatment of 3-chloro/bromobenzoic acids with hindered lithium dialkylamides (LDA or LTMP) at -50 °C, lithium 3-chloro/bromo-2-lithiobenzoates are generated. These dianions can be trapped as such to afford after electrophilic quenching a variety of simple 2-substituted-3-chloro/bromobenzoic acids. The 3-bromo-2-lithiobenzoate is less stable than the 3-chloro analog and partly eliminates lithium bromide, thus setting free lithium 2,3- and 3,4-dehydrobenzoates that can be intercepted in situ with the hindered base. After reading the article, we found that the author used 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Name: 3-Bromo-2-methylbenzoic acid)

3-Bromo-2-methylbenzoic acid(cas: 76006-33-2) 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. Name: 3-Bromo-2-methylbenzoic acid Alkyl bromides are mainly used as alkylating agents and also find application as a solvent to extract oil from seeds and wool.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2006,Xiao, Xiangshu; Antony, Smitha; Pommier, Yves; Cushman, Mark published 《Total Synthesis and Biological Evaluation of 22-Hydroxyacuminatine》.Journal of Medicinal Chemistry published the findings.Electric Literature of C8H7BrO2 The information in the text is summarized as follows:

A total synthesis of 22-hydroxyacuminatine, a cytotoxic alkaloid isolated from Camptotheca acuminata, is reported. The key step in the synthesis involves the reaction of 2,3-dihydro-1H-pyrrolo[3,4-b]quinoline with a brominated phthalide to generate a substituted pentacyclic 12H-5,11a-diazadibenzo[b,h]fluoren-11-one intermediate. Despite its structural resemblance to camptothecin and luotonin A, a biol. evaluation of 22-hydroxyacuminatine in a topoisomerase I-deficient cell line P388/CPT45 has confirmed that the observed cytotoxicity is not due to topoisomerase I inhibition, even though 22-hydroxyacuminatine has a hydroxyl group that can theor. hydrogen bond to Asp533. This result is consistent with the hypothesis that π-π stacking is more important than hydrogen-bonding interactions in determining topoisomerase I inhibitor binding in the ternary cleavage complex. In the experimental materials used by the author, we found 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Electric Literature of C8H7BrO2)

3-Bromo-2-methylbenzoic acid(cas: 76006-33-2) 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. Electric Literature of C8H7BrO2 Moreover, several studies demonstrate that the average proportion of bromine in drugs is significantly higher than that in natural products.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2015,Park, Kwang-su; Seo, Yujin; Kim, Mi Kyoung; Kim, Kyungdo; Kim, Yun Kyung; Choo, Hyunah; Chong, Youhoon published 《A curcumin-based molecular probe for near-infrared fluorescence imaging of tau fibrils in Alzheimer’s disease》.Organic & Biomolecular Chemistry published the findings.Product Details of 626-40-4 The information in the text is summarized as follows:

In recent years, there has been growing interest in the near-IR (NIR) fluorescence imaging of tau fibrils for the early diagnosis of Alzheimer’s disease (AD). In order to develop a curcumin-based NIR fluorescent probe for tau fibrils, structural modification of the curcumin scaffold was attempted by combining the following rationales: the curcumin derivative should preserve its binding affinity to tau fibrils, and, upon binding to tau fibrils, the probe should show favorable fluorescence properties. To meet these requirements, we designed a novel curcumin scaffold with various aromatic substituents. Among the series, the curcumin derivative 1c with a (4-dimethylamino-2,6-dimethoxy)phenyl moiety showed a significant change in its fluorescence properties (22.9-fold increase in quantum yield; Kd, 0.77 μM; λem, 620 nm; Φ, 0.32) after binding to tau fibrils. In addition, fluorescence imaging of tau-green fluorescent protein-transfected SHSY-5Y cells with 1c confirmed that 1c detected tau fibrils in live cells. After reading the article, we found that the author used 3,5-Dibromoaniline(cas: 626-40-4Product Details of 626-40-4)

3,5-Dibromoaniline(cas: 626-40-4) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Product Details of 626-40-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2016,Uzarewicz-Baig, Magdalena; Wilhelm, Rene published 《Straightforward Diastereoselective Synthesis of P-Chirogenic (1R)-1,8,8-Trimethyl-2,4-diaza-3-phosphabicyclo[3.2.1]octane 3-Oxides: Application as Chiral NMR Solvating Agents》.Heteroatom Chemistry published the findings.Application In Synthesis of 1-Bromo-2-isopropylbenzene The information in the text is summarized as follows:

A direct route to enantio- and diastereopure nitrogen-substituted phosphine oxides has been developed. The desired P-stereogenic compounds were obtained in good yields and high purity. The starting point of the synthesis was (+)-camphor, which is a readily available compound from the chiral pool. The new nitrogen-substituted phosphine oxides could be transformed from their pentavalent state to their trivalent form with N,O-bis(trimethylsilyl)acetamide, which makes them potential chiral ligands. It was possible to apply these compounds as chiral-solvating agents in chiral recognition experiments with a racemic alc. and acid. In addition to this study using 1-Bromo-2-isopropylbenzene, there are many other studies that have used 1-Bromo-2-isopropylbenzene(cas: 7073-94-1Application In Synthesis of 1-Bromo-2-isopropylbenzene) was used in this study.

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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Application In Synthesis of 1-Bromo-2-isopropylbenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2017,Duan, Hongliang; Li, Yu; Arora, Daleep; Xu, Depeng; Lim, Hui-Ying; Wang, Weidong published 《Discovery of a Benzamide Derivative That Protects Pancreatic β-Cells against Endoplasmic Reticulum Stress》.Journal of Medicinal Chemistry published the findings.COA of Formula: C9H9BrO2 The information in the text is summarized as follows:

Endoplasmic reticulum (ER) stress-mediated pancreatic insulin-producing β-cell dysfunction and death are critical elements in the onset and progression of both type 1 and type 2 diabetes. Here, through cell-based high throughput screening the authors identified benzamide derivatives as a novel class of β-cell protective agents against ER stress-induced dysfunction and death. Through structure-activity relationship optimization, a 3-(N-piperidinyl)methyl benzamide derivative I markedly protects β-cells against ER stress-induced dysfunction and death with near 100% maximum rescue activity and an EC50 value of 0.032 μM. Compound I alleviates ER stress in β-cells by suppressing ER stress-mediated activation of all three branches of unfolded protein response (UPR) and apoptotic genes. Finally, the authors show that I significantly lowers blood glucose levels and increases concomitant β-cell survival and number in a streptozotocin-induced diabetic mouse model. Identification of β-cell-protective small mols. against ER stress provides a new promising modality for the treatment of diabetes. The experimental part of the paper was very detailed, including the reaction process of Methyl 3-(bromomethyl)benzoate(cas: 1129-28-8COA of Formula: C9H9BrO2)

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. COA of Formula: C9H9BrO2 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 2017,Feng, Liheng; Deng, Yang; Wang, Xiaoju; Liu, Mingguang published 《Polymer fluorescent probe for Hg(II) with thiophene, benzothiazole and quinoline groups》.Sensors and Actuators, B: Chemical published the findings.Application of 626-40-4 The information in the text is summarized as follows:

A facile polymer consisted of quinoline, thiophene and benzothiazole groups was designed and synthesized by Suzuki coupling reaction. The study of photophys. property indicated that the polymer was a red light emitter with maximum absorption (490 nm) and emission (610 nm) peaks. The assays of thermal gravimetric anal. (TGA) and cyclic voltammetry (CV) revealed that the polymer possesses good thermal (Td, 228°C) and electrochem. properties. The exptl. data based on the cyclic voltammetry were in good agreement with the results of theor. calculations The sensing processes of the polymer to metal ions were investigated by UV-vis absorption and fluorescence emission spectra. The results showed that the polymer had high selectivity and sensitivity for Hg(II) ions with an obvious “”turn-on”” fluorescence in the presence of Hg(II). Noticeably, the polymer as a fluorescence probe can be applied in the detection in practical samples. The attribution of the work lies in providing a new strategy for design and application of polymer probes in anal. and testing fields. In the experiment, the researchers used 3,5-Dibromoaniline(cas: 626-40-4Application of 626-40-4)

3,5-Dibromoaniline(cas: 626-40-4) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Application of 626-40-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary