Author: Jessica.F

N,C-Disubstituted Biarylpalladacycles as Precatalysts for ppm Pd-Catalyzed Cross Couplings in Water under Mild Conditions was written by Thakore, Ruchita R.;Takale, Balaram S.;Gallou, Fabrice;Reilly, John;Lipshutz, Bruce H.. And the article was included in ACS Catalysis in 2019.Recommanded Product: Methyl 4-bromo-2-fluorobenzoate This article mentions the following:

Various mono- and di-substitution patterns on the parent biarylamine skeleton characteristic of palladacycles, as well as the counterion effect, have been studied looking to increase the effectiveness of the catalyst formed under micellar catalysis conditions in water, with the goal of reducing the amount of Pd needed for coupling reactions. Several substituted palladacycles containing readily accessible ligands were chosen for evaluation. The results indicate that: (1) pre-activation of Pd(II) salts as precursors for Suzuki-Miyaura (SM) couplings via treatment with a reducing agent is not required; (2) reactions could be performed with ca. half the loading of Pd relative to that previously required based on a combination of a Pd(II) salt and ligand; (3) the most effective palladacycle pre-catalyst has been identified as that containing an iso-Pr group on both an aryl ring and on nitrogen, together with the ligand EvanPhos and triflate as the counterion. This pre-catalyst is also effective in other C-C bond forming reactions, such as Heck and Sonogashira couplings. No organic solvents were needed for these processes, while the aqueous reaction medium could be recycled several times. A 1-pot, 4-step sequence involving Suzuki-Miyaura, reduction, alkylation, and acylation reactions highlights the potential for this pre-catalyst to maximize synthetic gain while minimizing costs and waste generation. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2Recommanded Product: Methyl 4-bromo-2-fluorobenzoate).

Methyl 4-bromo-2-fluorobenzoate (cas: 179232-29-2) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Recommanded Product: Methyl 4-bromo-2-fluorobenzoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Radical trifunctionalization of hexenenitrile via remote cyano migration was written by Chang, Chenyang;Zhang, Huihui;Wu, Xinxin;Zhu, Chen. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.Category: bromides-buliding-blocks This article mentions the following:

A novel radical-mediated trifunctionalization of hexenenitriles via the strategy of remote functional group migration is disclosed. A portfolio of functionalized hexenenitriles are employed as substrates. After difunctionalization of the unactivated alkenyl part via remote cyano migration, the in situ formed radical intermediate is captured by an azido radical, thus enabling the trifunctionalization. The reaction features mild conditions and broad functional group compatibility, leading to valuable products bearing multiple useful groups. This protocol further extends the scope of remote functional group migration. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Category: bromides-buliding-blocks).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon閳ユ彽romine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of S-alkylisothiuronium halides by reaction of thiourea with 锠?(4-hydroxyaryl)alkyl halides was written by Kandalintseva, N. V.;Prosenko, A. E.;Dyubchenko, O. I.;Stoyanov, E. S.. And the article was included in Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) in 2001.Category: bromides-buliding-blocks This article mentions the following:

A number of new S-arylalkylisothiuronium salts, e.g., I, were synthesized by reaction of 锠?[4-hydroxy(methoxy)aryl]alkyl halides with thiourea. The resulting isothiuronium salts in aqueous solution react with sodium (potassium) halides to form halogen exchange products. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Category: bromides-buliding-blocks).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Conjugated Dienes as Prohaptens in Contact Allergy: In Vivo and in Vitro Studies of Structure-Activity Relationships, Sensitizing Capacity, and Metabolic Activation was written by Bergstroem, Moa Andresen;Luthman, Kristina;Nilsson, J. Lars G.;Karlberg, Ann-Therese. And the article was included in Chemical Research in Toxicology in 2006.Recommanded Product: Isopentyltriphenylphosphonium bromide This article mentions the following:

There is a great interest in developing in vitro/in silico methods for the prediction of contact allergenic activity. However, many proposed methods do not take the activation of prohaptens to sensitizers by skin metabolism into account. As a consequence, consumer products containing potent sensitizers could be marketed. To identify prohaptens, studies regarding their structure-activity relationships and the mechanisms of their activation must be conducted. In the present investigation, we have studied the structure-activity relationships for alkene prohaptens. A series of seven alkenes (1-7), all of the same basic structure but with variation in the number and position(s) of the double bond(s), were designed and screened for sensitizing capacity using the murine local lymph node assay. Compounds 1-7 were also incubated with liver microsomes in the presence of glutathione to trap and identify reactive metabolites. The metabolic conversion of three alkenes (9-11) to epoxides (12-15) was also studied along with comparison of their sensitizing capacity. Our results show that conjugated dienes in or in conjunction with a six-membered ring are prohaptens that can be metabolically activated to epoxides and conjugated with GSH. Related alkenes containing isolated double bonds and an acyclic conjugated diene were shown to be weak or nonsensitizers. For the first time, the naturally occurring monoterpenes 浼?phellandrene, 灏?phellandrene, and 浼?terpinene were demonstrated to be prohaptens able to induce contact allergy. The difference in sensitizing capacity of conjugated dienes as compared to alkenes with isolated double bonds was found to be due to the high reactivity and sensitizing capacity of the allylic epoxides metabolically formed from conjugated dienes. We recommend that these structure-activity relationship rules are incorporated into in silico predictive databases and propose that the prediction of contact allergenic activity of suspected prohaptens is based on assessment of susceptibility to metabolic activation and chem. reactivity of potential metabolites. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Recommanded Product: Isopentyltriphenylphosphonium bromide).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Recommanded Product: Isopentyltriphenylphosphonium bromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Facile, direct reaction of benzaldehydes to 3-arylprop-2-enoic acids and 3-arylprop-2-ynoic acids in aqueous medium was written by Thiemann, Thies;Elshorbagy, Mohamed W.;Salem, Mostafa H. F. A.;Ahmadani, Siraj A. N.;Al-Jasem, Yosef;Al Azani, Mariam;Al-Sulaibi, Mazen A. M.;Al-Hindawi, Bassam. And the article was included in International Journal of Organic Chemistry in 2016.Recommanded Product: 3,5-Dibromo-4-methoxybenzaldehyde This article mentions the following:

Wittig reactions of benzaldehydes, alkanals, and cycloalkanals as well as of acetophenones are carried out with alkoxycarbonyl methylidenetriphenylphosphoranes in 10 w% aqueous NaOH, where the cinnamates and alkenoates produced are hydrolyzed in situ and the corresponding acids are obtained after mostly simple extractive work-up, often without employing organic solvents. Under the same conditions, benzaldehydes are reacted with alkoxycarbonyl bromomethylidenephosphorane to produce 3-arylprop-2-ynoic acids (arylpropiolic acids). In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Recommanded Product: 3,5-Dibromo-4-methoxybenzaldehyde).

3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Recommanded Product: 3,5-Dibromo-4-methoxybenzaldehyde

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Organic carboxylate salt-enabled alternative synthetic routes for bio-functional cyclic carbonates and aliphatic polycarbonates was written by Watanabe, Yuya;Takaoka, Shunya;Haga, Yuta;Kishi, Kohei;Hakozaki, Shunta;Narumi, Atsushi;Kato, Takashi;Tanaka, Masaru;Fukushima, Kazuki. And the article was included in Polymer Chemistry in 2022.Quality Control of 1-Bromo-4-methoxybutane This article mentions the following:

Simple and efficient synthetic routes for functionalized cyclic carbonates are indispensable for the practical application of side-chain bio-functionalized aliphatic polycarbonates as biodegradable functional biomaterials. In this study, a six-membered cyclic carbonate with a triethylammonium carboxylate has been prepared in one step from 2,2-bis(methylol)propionic acid (bis-MPA). We have demonstrated the suitability of the organic carboxylate salt of the bis-MPA cyclic carbonate for esterification with alkyl bromides via the S_N2 mechanism, leading to the formation of functionalized cyclic carbonate monomers. The esterification of the organic carboxylate salt proceeds efficiently when alkyl bromides with 浼?carbonyl, allyl, and benzyl groups are used. This approach enables a two-step synthesis of functionalized cyclic carbonates from bis-MPA. The organocatalyzed ring-opening polymerization of the resultant functionalized cyclic carbonates is effectively controlled, indicating that the synthetic process involving the organic carboxylate salt does not influence their polymerizability. The ether-functionalized aliphatic polycarbonates obtained from the organic carboxylate salt exhibit good antiplatelet properties, comparable to those of a previously developed blood-compatible aliphatic polycarbonate. The synthetic pathways exploiting organic carboxylate salts enable alternative shortcuts to functionalized cyclic carbonates from bis-MPA. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Quality Control of 1-Bromo-4-methoxybutane).

1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon鑱砨romine bond is electrophilic in nature. 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.Quality Control of 1-Bromo-4-methoxybutane

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Scalable anti-Markovnikov hydrobromination of aliphatic and aromatic olefins was written by Galli, Marzia;Fletcher, Catherine J.;del Pozo, Marc;Goldup, Stephen M.. And the article was included in Organic & Biomolecular Chemistry in 2016.Recommanded Product: 57293-19-3 This article mentions the following:

To improve access to a key synthetic intermediate a direct hydrobromination-Negishi route was targeted. Unsurprisingly, the anti-Markovnikov addition of HBr to estragole in the presence of AIBN proved successful. However, even in the absence of an added initiator, anti-Markovnikov addition was observed Re-examination of early reports revealed that selective Markovnikov addition, often simply termed “normal” addition, was not always observed with HBr unless air was excluded, leading to the rediscovery of a reproducible and scalable initiator-free protocol. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Recommanded Product: 57293-19-3).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Recommanded Product: 57293-19-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

A Biocatalytic Platform for Synthesis of Chiral 浼?Trifluoromethylated Organoborons was written by Huang, Xiongyi;Garcia-Borras, Marc;Miao, Kun;Kan, S. B. Jennifer;Zutshi, Arjun;Houk, K. N.;Arnold, Frances H.. And the article was included in ACS Central Science in 2019.Safety of 1-(2-Bromoethyl)-4-methoxybenzene This article mentions the following:

There are few biocatalytic transformations that produce fluorine-containing mols. prevalent in modern pharmaceuticals. To expand the scope of biocatalysis for organofluorine synthesis, we have developed an enzymic platform for highly enantioselective carbene B-H bond insertion to yield versatile 浼?trifluoromethylated (浼?CF₃) organoborons, an important class of organofluorine mols. that contain stereogenic centers bearing both CF₃ and boron groups. In contrast to current “carbene transferase” enzymes that use a limited set of simple diazo compounds as carbene precursors, this system based on Rhodothermus marinus cytochrome c (Rma cyt c) can accept a broad range of trifluorodiazo alkanes and deliver versatile chiral 浼?CF₃ organoborons with total turnovers up to 2870 and enantiomeric ratios up to 98.5:1.5. Computational modeling reveals that this broad diazo scope is enabled by an active-site environment that directs the alkyl substituent on the heme CF₃-carbene intermediate toward the solvent-exposed face, thereby allowing the protein to accommodate diazo compounds with diverse structural features. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Safety of 1-(2-Bromoethyl)-4-methoxybenzene).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) 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. 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.Safety of 1-(2-Bromoethyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Undecahydro-closo-dodecaborates as good leaving groups in organic synthesis: generation of substituted styrenes via elimination of arylethyl dodecaborates was written by Genady, Afaf R.;Nakamura, Hiroyuki. And the article was included in Organic & Biomolecular Chemistry in 2010.COA of Formula: C9H11BrO This article mentions the following:

New functionalized arylethyl undecahydro-closo-dodecaborates (S,S-disubstituted [B₁₂H₁₁SH]^2-, N,N-disubstituted [B₁₂H₁₁NH₃]^– and O-substituted [B₁₂H₁₁OH]^2-) are prepared by a simple one-step reaction. Moderate to good yields are obtained in the presence of various functional aryl groups. The synthesis of functionalized styrene derivatives can be readily achieved by treating arylethyl undecahydro-closo-dodecaborates with various bases. The scope and limitations of this procedure are demonstrated by investigating an array of alkylated dodecaborates. Based on an E2 elimination reaction, we identify the mechanistic pathway for dealkylation of arylethyl dodecaborates. Mechanistic studies indicate the following essential requirements to promote the elimination reaction: (i) the presence of 浼?CH acidity of the phenethyl group; (ii) steric hindrance; (iii) a substituted heteroatom on the closo-[B₁₂H₁₁]^2- cage and (iv) the presence of an electron-withdrawing group on the aromatic ring. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0COA of Formula: C9H11BrO).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.COA of Formula: C9H11BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis and biological evaluation of novel dimiracetam derivatives useful for the treatment of neuropathic pain was written by Farina, Carlo;Gagliardi, Stefania;Ghelardini, Carla;Martinelli, Marisa;Norcini, Monica;Parini, Carlo;Petrillo, Paola;Ronzoni, Silvano. And the article was included in Bioorganic & Medicinal Chemistry in 2008.Recommanded Product: 3-Bromo-4-fluorotoluene This article mentions the following:

Chem. modifications of dimiracetam (I), a bicyclic analog of the nootropic drug piracetam, afforded a small set of novel derivatives that were investigated in in vivo models of neuropathic pain. Compounds 5, 7 and 8 displayed a very promising antihyperalgesic profile in rat models of neuropathic pain induced by both chronic constriction injury of the sciatic nerve and streptozotocin. The compounds completely reverted the reduction of pain threshold evaluated by the paw pressure test. Importantly these derivatives did not induce any behavioral impairment as evaluated by the rotarod test. These results suggest that compounds 5, 7 and 8 might represent novel and well-tolerated therapeutic agents for the relief of neuropathic pain. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-fluorotoluene (cas: 452-62-0Recommanded Product: 3-Bromo-4-fluorotoluene).

3-Bromo-4-fluorotoluene (cas: 452-62-0) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Recommanded Product: 3-Bromo-4-fluorotoluene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary