Month: November 2022

《Ligand-Enabled Pd(II)-Catalyzed C(sp3)-H Lactonization Using Molecular Oxygen as Oxidant》 was written by Qian, Shaoqun; Li, Zi-Qi; Li, Minyan; Wisniewski, Steven R.; Qiao, Jennifer X.; Richter, Jeremy M.; Ewing, William R.; Eastgate, Martin D.; Chen, Jason S.; Yu, Jin-Quan. Synthetic Route of C8H7BrO2 And the article was included in Organic Letters in 2020. The article conveys some information:

Pd(II)-catalyzed C-H lactonization of o-Me benzoic acid substrates has been achieved using mol. oxygen as the oxidant. This finding provides a rare example of C-H oxygenation through Pd(II)/Pd(0) catalysis as well as a method to construct biol. important benzolactone scaffolds. The use of a gas mixture of 5% oxygen in nitrogen demonstrated the possibility for its application in pharmaceutical manufacturing In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzoic acid(cas: 76006-33-2Synthetic Route of C8H7BrO2)

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. Synthetic Route of C8H7BrO2 Due to the reactivity of bromide, they are used as potential precursors or important intermediates in organic synthesis.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Behavior, mechanism and equilibrium studies of Au(III) extraction with an ionic liquid [C4-6-C4BIm]Br2》 was written by Su, Hongmei; Wang, Qi; Wang, Ning; Yang, Yanzhao. Application In Synthesis of 1,6-Dibromohexane And the article was included in Dalton Transactions in 2020. The article conveys some information:

The first gemini-type benzimidazole ionic liquid ([C4-6-C4BIm]Br2) with two sites of action was synthesized and applied for gold extraction The effects of [C4-6-C4BIm]Br2 concentration, initial gold(III) concentration, acidity, and the loading capacity of [C4-6-C4BIm]Br2 were examined in detail. It was found that [C4-6-C4BIm]Br2 has excellent extraction ability for obtaining high purity gold. The anion exchange mechanism between [C4-6-C4BIm]Br2 and Au(III) was proved by Job’s method and 1H NMR and FTIR spectroscopy. Quantum chem. calculations were carried out to prove the mechanism theor. The extraction equilibrium process was modeled using Langmuir and Freundlich isotherms. Thermodn. parameters ΔH, ΔG and ΔS indicated that the extraction process was exothermic and spontaneous. The pseudo-second-order kinetic model well fitted the exptl. data (R = 0.99). In addition, [C4-6-C4BIm]Br2 has high selectivity for Au(III) compared to other base metals. In summary, [C4-6-C4BIm]Br2 has great application prospects in industry due to its excellent characteristics such as low cost, easy availability, and high extraction capacity. After reading the article, we found that the author used 1,6-Dibromohexane(cas: 629-03-8Application In Synthesis of 1,6-Dibromohexane)

1,6-Dibromohexane(cas: 629-03-8) is generally used to introduce C6 spacer in the molecular architecture. Some of the examples are: synthesis of pyrrolo-tetrathiafulvalene molecular bridge (6PTTF6) to study redox switching behavior of single molecules; synthesis of water-soluble thermoresponsive polylactides.Application In Synthesis of 1,6-Dibromohexane

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Cationic ether-free poly(bis-alkylimidazolium) ionene blend polybenzimidazole as anion exchange membranes》 was written by Dong, Jianhao; Yu, Na; Che, Xuefu; Liu, Ruihong; Aili, David; Yang, Jingshuai. SDS of cas: 623-24-5 And the article was included in Polymer Chemistry in 2020. The article conveys some information:

Two ether-free poly(bis-alkylimidazolium) ionenes with imidazolium cations as part of the main chain were synthesized from 1,4-bis(imidazolyl)butane and 1,4-dibromobutane or 1,4-bis(bromomethyl)benzene via nucleophilic substitution polymerization Anion exchange membranes (AEMs) were prepared by co-casting with polybenzimidazole (PBI), producing visually homogeneous and mech. robust blend AEMs. The ion exchange capacity (IEC), water uptake and ion conductivity could be balanced by adjusting the molar ratio of the poly(bis-alkylimidazolium) to PBI polymer in the blend. For example, the blend AEM of PBuIm-37%/PBI prepared from the oligomer derived from 1,4-dibromobutane with an IEC of 1.36 mmol g-1 showed a tensile strength of 5.3 MPa at room temperature and a hydroxide conductivity of 74 mS cm-1 at 80 °C and excellent stability over 500 h in 1 mol L-1 KOH at 60 °C. The present work opens up a new route towards ether-free AEM design and fabrication with a wide potential structural scope. In the experimental materials used by the author, we found 1,4-Bis(bromomethyl)benzene(cas: 623-24-5SDS of cas: 623-24-5)

1,4-Bis(bromomethyl)benzene(cas: 623-24-5) 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. SDS of cas: 623-24-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Cruz, Daniel A.; Sinka, Victoria; de Armas, Pedro; Steingruber, Hugo Sebastian; Fernandez, Israel; Martin, Victor S.; Miranda, Pedro O.; Padron, Juan I. published their research in Organic Letters in 2021. The article was titled 《Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes》.Related Products of 539-74-2 The article contains the following contents:

A new method that allowed the complete control of the regioselectivity of the hydrobromination reaction of alkenes was described. Herein, a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti-Markovnikov product occurs in the presence of ppm amounts of the Cu(I) species and the formation of the Markovnikov product occurred in the presence of 30 mol % iron(II) bromide was reported. D. functional theory calculations combined with Fukui’s radical susceptibilities support the obtained results. In the experiment, the researchers used Ethyl 3-bromopropanoate(cas: 539-74-2Related Products of 539-74-2)

Ethyl 3-bromopropanoate(cas: 539-74-2) belongs to organobromine compounds.The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides.Related Products of 539-74-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Iwamoto, Hiroaki; Tsuruta, Takuya; Ogoshi, Sensuke published their research in ACS Catalysis in 2021. The article was titled 《Development and Mechanistic Studies of (E)-Selective Isomerization/Tandem Hydroarylation Reactions of Alkenes with a Nickel(0)/Phosphine Catalyst》.Recommanded Product: Ethyltriphenylphosphonium bromide The article contains the following contents:

A stereoselective alkene isomerization and sequential hydroarylation with arylboronic acid using a nickel(0) catalyst was developed. The bulky monophosphine PAd2(n-Bu) was an effective ligand in these reactions to furnish both various stereo-defined internal alkenes and hydroarylation products (isomerization: up to 98%, E/Z = 98:2; tandem hydroarylation: up to 82%). Mechanistic studies based on experiments and computational calculations suggested that the isomerization proceeds via an intra- or intermol. hydrogen shift. Furthermore, a concerted multibond recombination with boronic acid-assisted oxidative protometallation of the alkene were found to be a reasonable mechanism for the formation of the alkylnickel(II) species from the alkene, nickel(0), alc., and boronic acid in the hydroarylation. After reading the article, we found that the author used Ethyltriphenylphosphonium bromide(cas: 1530-32-1Recommanded Product: Ethyltriphenylphosphonium bromide)

Ethyltriphenylphosphonium bromide(cas: 1530-32-1) is a phase transfer catalyst, used to accelerate the cure of phenolic-based epoxy resins, certain fluoroelastomer resins and thermosetting powder coatings. It is also used as catalysts in the synthesis of certain organic compounds and as a pharmaceutical intermediate.Recommanded Product: Ethyltriphenylphosphonium bromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Sarkar, Koushik; Das, Kuhali; Kundu, Abhishek; Adhikari, Debashis; Maji, Biplab published their research in ACS Catalysis in 2021. The article was titled 《Phosphine-Free Manganese Catalyst Enables Selective Transfer Hydrogenation of Nitriles to Primary and Secondary Amines Using Ammonia-Borane》.Formula: C5BrMnO5 The article contains the following contents:

The synthesis of primary amines RCH2NH2HCl [R = Ph, 2-phenylethyl, (1-oxo-1,3-dihydro-2-benzofuran-5-yl)methyl, etc.], 2,2′-(1,4-phenylene)bis(ethan-1-aminium) chloride, hexane-1,6-diaminium chloride sym. and unsym. secondary amines RCH2NHCH2R and RCH2NHR1 (R1 = pyridin-2-ylmethyl, cyclohexyl, n-Bu, etc.) by hydrogenation of nitriles RCN, 1,4-benzenediacetonitrile and hexanedinitrile, employing a borrowing hydrogenation strategy was reported. A class of phosphine-free manganese (I) complexes I [R2 = thiophen-2-yl, [2-(methylsulfanyl)phenyl]methyl, (2-methoxyphenyl)methyl, furan-2-yl] bearing sulfur side arms catalyzed the reaction under mild reaction conditions, where ammonia-borane is used as the source of hydrogen. The synthetic protocol is chemodivergent, as the final product is either primary or secondary amine, which can be controlled by changing the catalyst structure and the polarity of the reaction medium. The significant advantage of this method is that the protocol operates without externally added base or other additives as well as obviates the use of high-pressure dihydrogen gas required for other nitrile hydrogenation reactions. Utilizing this method, a wide variety of primary and sym. and asym. secondary amines were synthesized in high yields. A mechanistic study involving kinetic experiments and high-level DFT computations revealed that both outer-sphere dehydrogenation and inner-sphere hydrogenation were predominantly operative in the catalytic cycle. The experimental process involved the reaction of Bromopentacarbonylmanganese(I)(cas: 14516-54-2Formula: C5BrMnO5)

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.Formula: C5BrMnO5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Qiu, Shaotong; Gao, Xiang; Zhu, Shifa published their research in Chemical Science in 2021. The article was titled 《Dirhodium(II)-catalysed cycloisomerization of azaenyne: rapid assembly of centrally and axially chiral isoindazole frameworks》.Computed Properties of C4H7Br The article contains the following contents:

A dirhodium(II)-catalyzed asym. cycloisomerization reaction of azaenynes through a cap-tether synergistic modulation strategy, which represents the first catalytic asym. cycloisomerization of azaenynes. This reaction is highly challenging because of its inherent strong background reaction leading to racemate formation and the high capability of coordination of the nitrogen atom resulting in catalyst deactivation. Varieties of centrally chiral isoindazole derivatives was prepared in up to 99 : 1 d.r., 99 : 1 er and 99% yield and diverse enantiomerically enriched atropisomers bearing two five-membered heteroaryls was accessed by using an oxidative central-to-axial chirality transfer strategy. The tethered nitrogen atom incorporated into the starting materials enabled easy late-modifications of the centrally and axially chiral products via C-H functionalizations, which further demonstrated the appealing synthetic utilities of this powerful asym. cyclization.(Bromomethyl)cyclopropane(cas: 7051-34-5Computed Properties of C4H7Br) 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.Computed Properties of C4H7Br

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Yu, Zhen-Qiang; Li, Xiaodong; Wan, Wei; Li, Xin-Shun; Fu, Kuo; Wu, Yue; Li, Alexander D. Q. published their research in Chemical Science in 2021. The article was titled 《Cooperatively assembled liquid crystals enable temperature-controlled Forster resonance energy transfer》.Category: bromides-buliding-blocks The article contains the following contents:

Balancing the rigidity of a π-conjugated structure for strong emission and the flexibility of liquid crystals for self-assembly is the key to realizing highly emissive liquid crystals (HELCs). Here we show that (1) integrating organization-induced emission into dual mol. cooperatively-assembled liquid crystals, (2) amplifying mesogens, and (3) elongating the spacer linking the emitter and the mesogen create advanced materials with desired thermal-optical properties. Impressively, assembling the fluorescent acceptor Nile red into its host donor designed according to the aforementioned strategies results in a temperature-controlled Forster resonance energy transfer (FRET) system. Indeed, FRET exhibits strong S-curve dependence as temperature sweeps through the liquid crystal phase transformation. Such thermochromic materials, suitable for dynamic thermo-optical sensing and modulation, are anticipated to unlock new and smart approaches for controlling and directing light in stimuli-responsive devices. The results came from multiple reactions, including the reaction of 1,6-Dibromohexane(cas: 629-03-8Category: bromides-buliding-blocks)

1,6-Dibromohexane(cas: 629-03-8) is generally used to introduce C6 spacer in the molecular architecture. Some of the examples are: synthesis of pyrrolo-tetrathiafulvalene molecular bridge (6PTTF6) to study redox switching behavior of single molecules; synthesis of water-soluble thermoresponsive polylactides.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Nakashima, Yusei; Matsumoto, Junki; Nishikata, Takashi published their research in ACS Catalysis in 2021. The article was titled 《Iron-Catalyzed Stereoconvergent Tertiary Alkylation of (E)- and (Z)-Mixed Internal Olefins with Functionalized Tertiary Alkyl Halides》.SDS of cas: 1530-32-1 The article contains the following contents:

Herein, an efficient method for the stereoconvergent tertiary alkylations of (E)- and (Z)-mixed internal olefins (styrenes, enamides, and vinylic ethers) to produce trisubstituted olefins bearing a quaternary carbon center via an addition/elimination reaction in the presence of an iron catalyst. (E)- and (Z)-mixed internal olefins with various E/Z ratios reacted smoothly with α-bromocarbonyls as a tertiary alkyl source to exclusively produce (E)-trisubstituted olefins was reported. Mechanistic studies revealed that each of the (E)- and (Z)-internal olefins exhibited the same reactivity, and the exclusive generation of (E)-trisubstituted olefin products could be attributed to the β-hydrogen elimination of an alkyl iron species. The developed method can be used to synthesize highly congested trisubstituted olefins containing a quaternary carbon atom that bears various alkyl chains. In the experimental materials used by the author, we found Ethyltriphenylphosphonium bromide(cas: 1530-32-1SDS of cas: 1530-32-1)

Ethyltriphenylphosphonium bromide(cas: 1530-32-1) is a phase transfer catalyst, used to accelerate the cure of phenolic-based epoxy resins, certain fluoroelastomer resins and thermosetting powder coatings. It is also used as catalysts in the synthesis of certain organic compounds and as a pharmaceutical intermediate.SDS of cas: 1530-32-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tsushima, Takumi; Tanaka, Hideya; Nakanishi, Kazuki; Nakamoto, Masaaki; Yoshida, Hiroto published an article in 2021. The article was titled 《Origins of Internal Regioselectivity in Copper-Catalyzed Borylation of Terminal Alkynes》, and you may find the article in ACS Catalysis.Safety of 1-Bromo-3,4,5-trimethoxybenzene The information in the text is summarized as follows:

Installation of a boron functionality into a more substituted carbon of terminal alkynes has been a challenging issue in chem. synthesis, since inherently Lewis acidic boron moieties, in principle, favor their attachment to a terminal carbon. Herein, we report on the highly internal-selective borylation of terminal alkynes under copper catalysis, wherein diminishment of boron-Lewis acidity and ligand-derived steric bulk around a copper center are the key to the success. In particular, the use of an anthranilamide-substituted boron moiety [B(aam)] is of high synthetic significance, because its properly diminished Lewis acidity enabled the internal regioselectivity and the Suzuki-Miyaura cross-coupling activity to be compatibly achieved. This method provided a direct and universal approach to variously substituted branched alkenylboron compounds, regardless of electronic and steric properties of a substituent on terminal alkynes. In the experiment, the researchers used many compounds, for example, 1-Bromo-3,4,5-trimethoxybenzene(cas: 2675-79-8Safety of 1-Bromo-3,4,5-trimethoxybenzene)

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.Safety of 1-Bromo-3,4,5-trimethoxybenzene1-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