Tag: 200-300

《Photon Equivalents as a Parameter for Scaling Photoredox Reactions in Flow: Translation of Photocatalytic C-N Cross-Coupling from Lab Scale to Multikilogram Scale》 was written by Corcoran, Emily B.; McMullen, Jonathan P.; Levesque, Francois; Wismer, Michael K.; Naber, John R.. COA of Formula: C7H4BrF3 And the article was included in Angewandte Chemie, International Edition in 2020. The article conveys some information:

With the development of new photocatalytic methods over recent decades, the translation of these chem. reactions to industrial-production scales using continuous-flow reactors has become a topic of increasing interest. In this context, we describe our studies toward elucidating an empirically derived parameter for scaling photocatalytic reactions in flow. By evaluating the performance of a photocatalytic C-N cross-coupling reaction across multiple reactor sizes and geometries, it was demonstrated that expressing product yield as a function of the absorbed photon equivalent provides a predictive, empirical scaling parameter. Through the use of this scaling factor and characterization of the photonic flux within each reactor, the cross-coupling was scaled successfully from the milligram scale in batch to a multi-kilogram reaction in flow. After reading the article, we found that the author used 1-Bromo-4-(trifluoromethyl)benzene(cas: 402-43-7COA of Formula: C7H4BrF3)

1-Bromo-4-(trifluoromethyl)benzene(cas: 402-43-7) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. The most pervasive is the naturally produced bromomethane.COA of Formula: C7H4BrF3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations》 was written by Fricke, Christoph; Deckers, Kristina; Schoenebeck, Franziska. Related Products of 2675-79-8 And the article was included in Angewandte Chemie, International Edition in 2020. The article conveys some information:

While halogenation is of key importance in synthesis and radio-imaging, the currently available repertoire is largely designed to introduce a single halogen per mol. This report makes the selective introduction of several different halogens accessible. Showcased here is the privileged stability of nontoxic aryl germanes under harsh fluorination conditions (that allow selective fluorination in their presence), while displaying superior reactivity and functional-group tolerance in electrophilic iodinations and brominations, out-competing silanes or boronic esters under rapid and additive-free conditions. Mechanistic experiments and computational studies suggest a concerted electrophilic aromatic substitution as the underlying mechanism. The results came from multiple reactions, including the reaction of 1-Bromo-3,4,5-trimethoxybenzene(cas: 2675-79-8Related Products of 2675-79-8)

1-Bromo-3,4,5-trimethoxybenzene(cas: 2675-79-8) is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.Related Products of 2675-79-81-Bromo-3,4,5-trimethoxybenzene can be used to synthesize N,N′-diarylated indolo[3,2-b]carbazole derivatives, which can find applications in electrophotography.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Lessons in Strain and Stability: Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid》 was written by Hancock, Erin N.; Kuker, Erin L.; Tantillo, Dean J.; Brown, M. Kevin. HPLC of Formula: 17696-11-6 And the article was included in Angewandte Chemie, International Edition in 2020. The article conveys some information:

The synthesis of structurally complex and highly strained natural products provides unique challenges and unexpected opportunities for the development of new reactions and strategies. Herein, the synthesis of (+)-[5]-ladderanoic acid (I) is reported. En route to the target, unusual and unexpected strain release driven transformations were uncovered. This occurrence required a drastic revision of the synthetic design that ultimately led to the development of a novel stepwise cyclobutane assembly by an allylboration/Zweifel olefination sequence. In the experiment, the researchers used 8-Bromooctanoic acid(cas: 17696-11-6HPLC of Formula: 17696-11-6)

8-Bromooctanoic acid(cas: 17696-11-6) acid is used in the synthesis of 8-(N-Methyl-4,4′-bipyridinyl)- octanoic acid. 8-Mercaptooctanoic acid was prepared from 8-bromooctanoic acid. And 8-Bromooctanoic Acid is a useful compound for sonodynamic therapy.HPLC of Formula: 17696-11-6

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《A Bioorthogonal Click Chemistry Toolbox for Targeted Synthesis of Branched and Well-Defined Protein-Protein Conjugates》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Baalmann, Mathis; Neises, Laura; Bitsch, Sebastian; Schneider, Hendrik; Deweid, Lukas; Werther, Philipp; Ilkenhans, Nadja; Wolfring, Martin; Ziegler, Michael J.; Wilhelm, Jonas; Kolmar, Harald; Wombacher, Richard. Application In Synthesis of 8-Bromooctanoic acid The article mentions the following:

Bioorthogonal chem. holds great potential to generate difficult-to-access protein-protein conjugate architectures. Current applications are hampered by challenging protein expression systems, slow conjugation chem., use of undesirable catalysts, or often do not result in quant. product formation. Here the authors present a highly efficient technol. for protein functionalization with commonly used bioorthogonal motifs for Diels-Alder cycloaddition with inverse electron demand (DAinv). With the aim of precisely generating branched protein chimeras, the authors systematically assessed the reactivity, stability and side product formation of various bioorthogonal chemistries directly at the protein level. The authors demonstrate the efficiency and versatility of the authors′ conjugation platform using different functional proteins and the therapeutic antibody trastuzumab. This technol. enables fast and routine access to tailored and hitherto inaccessible protein chimeras useful for a variety of scientific disciplines. The authors expect the authors′ work to substantially enhance antibody applications such as immunodetection and protein toxin-based targeted cancer therapies. In the experiment, the researchers used many compounds, for example, 8-Bromooctanoic acid(cas: 17696-11-6Application In Synthesis of 8-Bromooctanoic acid)

8-Bromooctanoic acid(cas: 17696-11-6) acid is used in the synthesis of 8-(N-Methyl-4,4′-bipyridinyl)- octanoic acid. 8-Mercaptooctanoic acid was prepared from 8-bromooctanoic acid. And 8-Bromooctanoic Acid is a useful compound for sonodynamic therapy.Application In Synthesis of 8-Bromooctanoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2017,Bhattarai, Deepak; Jung, Joo Hyun; Han, Seunghyeon; Lee, Hankyu; Oh, Soo Jin; Ko, Hyuk Wan; Lee, Kyeong published 《Design, synthesis, and biological evaluation of structurally modified isoindolinone and quinazolinone derivatives as hedgehog pathway inhibitors》.European Journal of Medicinal Chemistry published the findings.Application of 76006-33-2 The information in the text is summarized as follows:

The Hedgehog (Hh) signaling pathway is associated with diverse aspects of cellular events, such as cell migration, proliferation, and differentiation throughout embryonic development and tissue patterning. An abnormal Hh signaling pathway is linked to numerous human cancers, including basal cell carcinoma (BCC), medulloblastoma (MB), lung cancer, prostate cancer, and ovarian cancer, and it is therefore a promising target in cancer therapy. Using a structure-hopping approach, we designed new Hh signaling pathway inhibitors with isoindolinone or quinazolinone moieties, which were synthesized and biol. evaluated using an 8xGli-luciferase (Gli-Luc) reporter assay in NIH3T3 cells. Compounds with isoindolinone scaffolds demonstrated moderate Hh inhibitory activity; whereas quinazolinone derivatives exhibited good potency with submicromolar IC50 values and the analog I showed nanomolar IC50 value. Although sonidegib shows a decrease in inhibitory effect on vismodegib resistance-conferring Smo mutants, the structurally modified new compounds not only possess the pharmacophoric properties of Hh pathway inhibition but also preserve the suppressive potency in drug-resistant Smo mutants. Mechanistically, quinazolinone derivatives I and II suppress Hh signaling by blocking Smo and Gli translocation into the cilia, similar to vismodegib and sonidegib. Addnl., the human microsomal stability of the representative analogs I and II were determined to be comparable to that of the reference compound sonidegib. Thus, these new scaffolds can serve as a platform for the development of novel cancer therapeutics targeting the Hh pathway. The results came from multiple reactions, including the reaction of 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Application of 76006-33-2)

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. Application of 76006-33-2 Due to the reactivity of bromide, they are used as potential precursors or important intermediates in organic synthesis.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2015,Schweighauser, Luca; Strauss, Marcel A.; Bellotto, Silvia; Wegner, Hermann A. published 《Attraction or Repulsion? London Dispersion Forces Control Azobenzene Switches》.Angewandte Chemie, International Edition published the findings.Recommanded Product: 3,5-Dibromoaniline The information in the text is summarized as follows:

Large substituents are commonly seen as entirely repulsive through steric hindrance. Such groups have addnl. attractive effects arising from weak London dispersion forces between the neutral atoms. Steric interactions are recognized to have a strong influence on isomerization processes, such as in azobenzene-based mol. switches. Textbooks indicate that steric hindrance destabilizes the Z isomers. Herein, increasing the bulkiness of electronically equal substituents in the meta-position decreases the thermal reaction rates from the Z to the E isomers. DFT computations revealed that attractive dispersion forces essentially lower the energy of the Z isomers. In the experimental materials used by the author, we found 3,5-Dibromoaniline(cas: 626-40-4Recommanded Product: 3,5-Dibromoaniline)

3,5-Dibromoaniline(cas: 626-40-4) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.Recommanded Product: 3,5-Dibromoaniline

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Usutani, Hirotsugu; Cork, David G. published an article in Organic Process Research & Development. The title of the article was 《Effective Utilization of Flow Chemistry: Use of Unstable Intermediates, Inhibition of Side Reactions, and Scale-Up for Boronic Acid Synthesis》.Formula: C12H15BrO The author mentioned the following in the article:

Flow chem. processes for boronic acid syntheses utilizing lithiation-borylation have been developed. The side reactions in the lithiation step that occur in batch were suppressed, and unstable lithium intermediates were handled safely. Flow technol. was applied to several kinds of boronic acid syntheses, and scale-up was successfully conducted to allow kilogram-scale production Some of the key benefits of flow flash chem. were utilized, both to avoid side reactions and to enable dianion chem. that is difficult to perform successfully in batch reactions. The examples showed further perspectives on the utility of flow technologies for process development. In the experimental materials used by the author, we found 1-Bromo-4-(cyclohexyloxy)benzene(cas: 30752-31-9Formula: C12H15BrO)

1-Bromo-4-(cyclohexyloxy)benzene(cas: 30752-31-9) 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. Formula: C12H15BrO In contrast, terrestrial plants account only for a few bromine-containing compounds.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Fier, Patrick S.; Maloney, Kevin M. published an article on January 30 ,2019. The article was titled 《NHC-Catalyzed Deamination of Primary Sulfonamides: A Platform for Late-Stage Functionalization》, and you may find the article in Journal of the American Chemical Society.Recommanded Product: 25195-52-2 The information in the text is summarized as follows:

Primary alkyl and aryl sulfonamides underwent chemoselective deamination reactions with benzaldehyde and K2CO3 in the presence of a pyrrolotriazolium chloride via N-benzylidenesulfonamides to yield sulfinate salts; the sulfinates were converted in situ to Me and aryl sulfones, sulfonic acids, and sulfonamides. Reaction of the sulfinates with MeI in DMF yielded Me sulfones, while oxidation with H2O2 in the presence of tungstic acid yielded sulfonic acids. Reaction of the sulfinate generated from celecoxib with 15NH4OH yielded the corresponding 15N-labeled sulfonamide; coupling reactions of the celecoxib-derived sulfinate with iodobenzene and a chloropyridine yielded aryl sulfones, while desulfonative coupling with Ph triflate yielded a biphenylpyrazole. The method tolerated nearly all common functional groups, including primary amines, and was used for the late-stage derivatization of several complex pharmaceutical compounds In the part of experimental materials, we found many familiar compounds, such as 1-Bromo-2-((methylsulfonyl)methyl)benzene(cas: 25195-52-2Recommanded Product: 25195-52-2)

1-Bromo-2-((methylsulfonyl)methyl)benzene(cas: 25195-52-2) belongs to organobromine compounds.The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. Recommanded Product: 25195-52-2 The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Dutta, Shubham; Yang, Shengwen; Vanjari, Rajeshwer; Mallick, Rajendra K.; Gandon, Vincent; Sahoo, Akhila K. published an article in Angewandte Chemie, International Edition. The title of the article was 《Keteniminium-Driven Umpolung Difunctionalization of Ynamides》.Computed Properties of C6H5BBr2O2 The author mentioned the following in the article:

A three-component Pd-catalyzed coupling of ynamides, aryl diazonium salts, and aryl boronic acids for the synthesis of novel triaryl-substituted enamides is described. This transformation represents the first example of an umpolung regioselective unsym. syn-1,2-diarylation/aryl-olefination of ynamides. The aryl moieties of the diazonium salt (electrophile) and boronic acid (nucleophile) are explicitly incorporated in the electrophilic α- and nucleophilic β-position, resp., of the ynamide, resulting in a single isomer of the N-bearing tetrasubstituted olefin. The scope is broad (68 examples), showing excellent functional-group tolerance. DFT calculations substantiate the rationale of the mechanistic cycle and the regioselectivity. The chemoselectivity and synthetic potential of the enamide products were also studied.3,4-Dibromophenylboronic acid(cas: 1228180-83-3Computed Properties of C6H5BBr2O2) was used in this study.

3,4-Dibromophenylboronic acid(cas: 1228180-83-3) 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. Computed Properties of C6H5BBr2O2 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

SDS of cas: 403646-48-0On November 30, 2001 ,《1,2-Didehydro-3- and -4-(trifluoromethoxy)benzene: the “”aryne”” route to 1- and 2-(trifluoromethoxy)naphthalenes》 appeared in European Journal of Organic Chemistry. The author of the article were Schlosser, Manfred; Castagnetti, E.. The article conveys some information:

Upon treatment of 1-bromo-2-(trifluoromethoxy)benzene with lithium diisopropylamide (LDA) at -100°C, 3-bromo-2-(trifluoromethoxy)phenyllithium is generated. It can be trapped as such, but isomerizes to afford 2-bromo-6-(trifluoromethoxy)phenyllithium when the temperature is raised to -75°C. The latter intermediate can be directly obtained from 1-bromo-3-(trifluoromethoxy)benzene. 1-Bromo-4-(trifluoromethoxy)benzene gives 5-bromo-2-(trifluoromethoxy)phenyllithium at -100°C, but at -75°C it slowly eliminates lithium bromide, thus setting free 1,2-dehydro-4-(trifluoromethoxy)benzene. In the same way, 1,2-dehydro-3-(trifluoromethoxy)benzene can be generated from 1-bromo-3-(trifluoromethoxy)benzene. Both arynes can be intercepted in situ with furan. The resulting [4+2] cycloadducts can be reduced with zinc powder, giving 1- and 2-(trifluoromethoxy)naphthalenes, they may be submitted to acid-catalyzed isomerization to produce trifluoromethoxy-1-naphthols, or they may be brominated to afford vic-dibromo derivatives Base-promoted dehydrobromination of the latter compounds produces 2- or 3-bromo-1,4-epoxy-1,4-dihydro-5- or -6-(trifluoromethoxy)naphthalenes, which undergo regioselective ring-opening in acidic media and halogen/metal exchange when treated with butyllithium. In the part of experimental materials, we found many familiar compounds, such as 2-Bromo-5-(trifluoromethoxy)benzoic acid(cas: 403646-48-0SDS of cas: 403646-48-0)

2-Bromo-5-(trifluoromethoxy)benzoic acid(cas: 403646-48-0) 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. SDS of cas: 403646-48-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary