Category: 57293-19-3

Introduction of Cyclopropyl and Cyclobutyl Ring on Alkyl Iodides through Cobalt-Catalyzed Cross-Coupling was written by Andersen, Claire;Ferey, Vincent;Daumas, Marc;Bernardelli, Patrick;Guerinot, Amandine;Cossy, Janine. And the article was included in Organic Letters in 2019.Category: bromides-buliding-blocks This article mentions the following:

A cobalt-catalyzed cross-coupling between alkyl iodides and cyclopropyl, cyclobutyl, and alkenyl Grignard reagents is disclosed. The reaction allows the introduction of strained rings on a large panel of primary and secondary alkyl iodides. The catalytic system is simple and nonexpensive, and the reaction is general, chemoselective, and diastereoconvergent. The alkene resulting from the cross-coupling can be transformed to substituted cyclopropanes using a Simmons-Smith reaction. The formation of radical intermediates during the coupling is hypothesized. 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. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of quinoline-based NNN-pincer nickel(II) Complexes: a robust and improved catalyst system for C-H bond alkylation of azoles with alkyl halides was written by Patel, Ulhas N.;Pandey, Dilip K.;Gonnade, Rajesh G.;Punji, Benudhar. And the article was included in Organometallics in 2016.HPLC of Formula: 57293-19-3 This article mentions the following:

The quinoline-based pincer nickel(II) complexes I (2a,b, X = Cl, R = Me, Et; 3a,b, X = Br, R = Me, Et; 4a, X = OAc, R = Me) were prepared by the reaction of the ligand precursors N-[(2-dialkylamino)phenyl]-8-quinolinamines with (DME)NiCl₂ (THF)₂NiBr₂ or Ni(OAc)₂ in the presence of Et₃N. All of these complexes were characterized by ¹H and ¹³C NMR spectroscopy as well as by elemental anal. Further, the mol. structures of 2a and 3a,b were elucidated by x-ray crystallog. Complex 2a is found to be an efficient catalyst for the direct C-H bond alkylation of substituted benzothiazoles and oxazoles in 2-position with various unactivated alkyl halides containing 灏?hydrogens under mild reaction conditions. The catalyst 2a is very robust and was recycled and reused five times for the alkylation reaction without a decrease in its catalytic activity. Preliminary studies reveal that the catalyst 2a acts as an active catalyst and the alkylation reaction appears to operate via a radical pathway. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3HPLC of Formula: 57293-19-3).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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.HPLC of Formula: 57293-19-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Highly efficient synthesis of alkylboronate esters via Cu(II)-catalyzed borylation of unactivated alkyl bromides and chlorides in air was written by Bose, Shubhankar Kumar;Brand, Simon;Omoregie, Helen Oluwatola;Haehnel, Martin;Maier, Jonathan;Bringmann, Gerhard;Marder, Todd B.. And the article was included in ACS Catalysis in 2016.Synthetic Route of C10H13BrO This article mentions the following:

A copper(II)-catalyzed borylation of alkyl halides with bis(pinacolato)diboron (B₂pin₂) has been developed, which can be carried out in air, providing a wide range of primary, secondary, and some tertiary alkylboronates in high yields. A variety of functional groups are tolerated and the protocol is also applicable to unactivated alkyl chlorides (including 1,1- and 1,2-dichlorides). Preliminary mechanistic investigations show that this borylation reaction involves one-electron processes. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Synthetic Route of C10H13BrO).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) 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). The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Synthetic Route of C10H13BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Combination of Methods for in Vitro Study of Antioxidant Properties of Chemical Compounds was written by Menshchikova, E. B.;Zenkov, N. K.;Kandalintseva, N. V.;Prosenko, A. E.. And the article was included in Bulletin of Experimental Biology and Medicine in 2008.HPLC of Formula: 57293-19-3 This article mentions the following:

We proposed a combination of methods to study antioxidant properties of compounds, including evaluation of the capacity of the test preparations to inhibit peroxidation of unsaturated lipids (in model systems with oxidation of Et oleate; aqueous emulsion medium) and low-d. lipoproteins (in the presence of transition metal ions), generation of superoxide anion radical (system of lucigenin, xanthine oxidase, and xanthine) and NO·/ONOO- (system of SIN-1 and lucigenin), and induction of respiratory burst in blood granulocytes (luminol-induced and lucigenin-induced reaction after zymosan stimulation). In vitro study showed that the antioxidant properties of synthetic watersol. phenols depend strongly on masking of the phenol OH group and nature of the ionogenic fragment in the p-Pr substituent. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3HPLC of Formula: 57293-19-3).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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.HPLC of Formula: 57293-19-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Silicon-Carbon Bond Formation via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Unactivated Secondary and Tertiary Alkyl Electrophiles was written by Chu, Crystal K.;Liang, Yufan;Fu, Gregory C.. And the article was included in Journal of the American Chemical Society in 2016.Reference of 57293-19-3 This article mentions the following:

A wide array of cross-coupling methods for the formation of C-C bonds from unactivated alkyl electrophiles were described in recent years. In contrast, progress in the development of methods for the construction of C-heteroatom bonds has lagged; for example, there were no reports of metal-catalyzed cross-couplings of unactivated secondary or tertiary alkyl halides with Si nucleophiles to form C-Si bonds. The authors address this challenge, establishing that a simple, com. available Ni catalyst (NiBr₂·diglyme) can achieve couplings of alkyl bromides with nucleophilic Si reagents under unusually mild conditions (e.g., -20°); especially noteworthy is the authors’ ability to employ unactivated tertiary alkyl halides as electrophilic coupling partners, which is still relatively uncommon in the field of cross-coupling chem. Stereochem., relative reactivity, and radical-trap studies are consistent with a homolytic pathway for C-X bond cleavage. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Reference of 57293-19-3).

1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. 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.Reference of 57293-19-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The addition of halogen derivatives to allylbenzenes in the presence of peroxides; preparation of ω-bromopropylbenzenes was written by Quelet, Raymond;Durand-Dran, Raymonde;Pineau, Robert. And the article was included in Compt. rend. in 1957.Electric Literature of C10H13BrO This article mentions the following:

Despite the presence of a normally unreactive double bond, RC₆H₄CH₂CH:CH₂ (I) were converted to RC₆H₄CH₂CH₂Br (II) by treatment with HBr under the conditions of the Kharasch reaction (cf. C.A. 41, 4769h). Although no details are given, CCl₄ and CHBr₃ also added to I in the presence of Ac₂O to give satisfactory yields of the polyhalogenated butylbenzenes. I (in C₆H₆ solution only if the II crystallized) were treated gradually with 4-8% Bz₂O₂ in C₆H₆ or Ac₂O in Et₂O and saturated with dry HBr gas at 0-10° in a long cylindrical tube. The saturated mixture was freed of excess HBr at room temperature with a stream of air, washed, neutralized, treated with Na₂S₂O₄ solution, and distilled in vacuo. The II were identified by conversion to RC₆H₄CH₂CH₂CH₂CO₂H (III) by formation of their Grignard compounds in Et₂O or tetrahydrofuran or in some cases via the nitriles. The following II were prepared (R, b.p./mm., % yield, and m.p. of III given): H, 113-15°/16, 80, 50°; o-Me, 75-6°/0.35, 66, 59-60°; m-Me, 85-6°/1.1, 80, 37.5°; p-Me, 75-8°/0.7, 70, 58°; p-MeO, 85°/0.8, 70, 58°; 3,4-di-MeO (IV), 108-10°/0.01, 55, -. III were formed in good yields except from IV where demethylation took place in the Grignard preparation In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Electric Literature of C10H13BrO).

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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Electric Literature of C10H13BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Studies on the Formal [3 + 2] Cycloaddition of Aziridines with Alkenes for the Synthesis of 1-Azaspiroalkanes was written by Martinand-Lurin, Elodie;Gruber, Raymond;Retailleau, Pascal;Fleurat-Lessard, Paul;Dauban, Philippe. And the article was included in Journal of Organic Chemistry in 2015.Application In Synthesis of 1-(3-Bromopropyl)-4-methoxybenzene This article mentions the following:

The Lewis acid-mediated [3+2] cycloaddition of N-sulfonyl- and N-sulfamoylaziridines with alkenes provides a rapid and efficient access to 1-azaspiro[4.n]alkanes. Exptl. studies have been combined with DFT calculations to explore the mechanism of the reaction. They demonstrate that the nature of the electron-withdrawing nitrogen protecting group has a very limited influence on the course of the reaction and, particularly, on the initial formation of the 1,3-zwitterionic species through C-N bond cleavage, which has been found to be the rate-determining step. Compared to N-sulfonylaziridines, N-sulfamoylaziridines have proved to be more synthetically useful synthons that afford crystalline polycyclic structures in good yields. A short sequence of catalytic C(sp³)-H amination-cyclization-[3+2] cycloaddition has then been successfully designed to afford the homolog 1-azaspiro[5.n]alkanes, thereby illustrating the higher versatility of sulfamates in these cycloadditions In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Application In Synthesis of 1-(3-Bromopropyl)-4-methoxybenzene).

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

First Total Synthesis of ω-Phenyl Δ6 Fatty Acids and their Leishmanicidal and Anticancer Properties was written by Carballeira, Nestor M.;Morales-Guzman, Christian;Alvarez-Benedicto, Ester;Torres-Martinez, Zally;Delgado, Yamixa;Griebenow, Kai H.;Tinoco, Arthur D.;Reguera, Rosa M.;Perez-Pertejo, Yolanda;Carbajo-Andres, Ruben;Balana-Fouce, Rafael. And the article was included in Current Topics in Medicinal Chemistry (Sharjah, United Arab Emirates) in 2018.Formula: C10H13BrO This article mentions the following:

The first total synthesis of ω-Ph Δ6 fatty acids (FA), e.g., 10-cyclohexyl-6-decynoic acid, 16-phenylhexadecanoic acid, and (Z)-10-Phenyl-6-decenoic acid, and their cytotoxicity (A549) and leishmanicidal (L. infantum) activities are described. The novel 16-phenyl-6-hexadecynoic acid and the known 16-phenylhexadecanoic acid were synthesized in 7-8 steps with overall yields of 46% and 41%, resp. The syntheses of the unprecedented 10-phenyl-6-decynoic acid, 10-cyclohexyl-6-decynoic acid and 10-(4-methoxyphenyl)-6-decynoic acid was also performed in 3 steps with 73-76% overall yields. The use of lithium acetylide coupling enabled the 4-step synthesis of 10-phenyl-6Z-decenoic acid with a 100% cis-stereochem. The cytotoxicity of these novel FA was determined against A549 cells and L. infantum promastigotes and amastigotes. Among the ω-phenylated FA, the best cytotoxicity towards A549 was displayed by 16-phenyl-6-hexadecynoic acid, with an IC₅₀ of 18 ± 1 μM. On the other hand, among the C₁₀ acids, 10-cyclohexyl-6-decynoic acid presented the best cytotoxicity (IC₅₀ = 40 ± 2 μM) towards A549. Based on caspase-3/7 studies, neither of the FA induced apoptosis in A549, thus implying other mechanisms of cell death. The antileishmanial studies were performed with the top Leishmania donovani topoisomerase IB (LdTopIB) inhibitors, namely 16-phenyl-6-hexadecynoic acid and 16-phenylhexadecanoic acid (EC₅₀ between 14 and 36 μM, resp.), acids that did not stabilize the cleavage complexes between LdTopIB and DNA. Acids 16-phenyl-6-hexadecynoic acid and 16-phenylhexadecanoic acid displayed cytotoxicity towards L. infantum amastigotes (IC₅₀ = 3-6 μM) and L. infantum promastigotes (IC₅₀ = 60-70 μM), but low toxicity towards murine splenocytes. This results identified 16-phenyl-6-hexadecynoic acid as the optimum ω-phenylated acid of the series. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Formula: C10H13BrO).

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.Formula: C10H13BrO

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of Sultams and Cyclic N-Sulfonyl Ketimines via Iron-Catalyzed Intramolecular Aliphatic C-H Amidation was written by Zhong, Dayou;Wu, Di;Zhang, Yan;Lu, Zhiwu;Usman, Muhammad;Liu, Wei;Lu, Xiuqiang;Liu, Wen-Bo. And the article was included in Organic Letters in 2019.Safety of 1-(3-Bromopropyl)-4-methoxybenzene This article mentions the following:

Cyclic sulfonamides (sultams) play a unique role in drug discovery and synthetic chem. A direct synthesis of sultams by an intramol. C(sp³)-H amidation reaction using an iron complex in situ derived from Fe(ClO₄)₂ and aminopyridine ligand is reported. This strategy features a readily available catalyst and tolerates a broad variety of substrates as demonstrated by 22 examples (up to 89% yield). A one-pot iron-catalyzed amidation/oxidation procedure for the synthesis of cyclic N-sulfonyl ketimines is also realized with up to 92% yield (eight examples). The synthetic utility of the method is validated by a gram-scale reaction and derivatization of the products to ring-fused sultams. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Safety of 1-(3-Bromopropyl)-4-methoxybenzene).

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. 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.Safety of 1-(3-Bromopropyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles was written by Cong, Huan;Fu, Gregory C.. And the article was included in Journal of the American Chemical Society in 2014.Safety of 1-(3-Bromopropyl)-4-methoxybenzene This article mentions the following:

As part of our ongoing effort to expand the scope of cross-coupling reactions of alkyl electrophiles, we have pursued a strategy wherein the nucleophilic coupling partner includes a pendant olefin; after transmetalation by such a substrate, if β-migratory insertion proceeds faster than direct cross-coupling, an addnl. carbon-carbon bond and stereocenter can be formed. With the aid of a nickel/diamine catalyst (both components are com. available), we have established the viability of this approach for the catalytic asym. synthesis of 2,3-dihydrobenzofurans and indanes. Furthermore, we have applied this new method to the construction of the dihydrobenzofuran core of fasiglifam, as well as to a cross-coupling with a racemic alkyl electrophile; in the latter process, the chiral catalyst controls two stereocenters, one that is newly generated in a β-migratory insertion and one that begins as a mixture of enantiomers. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Safety of 1-(3-Bromopropyl)-4-methoxybenzene).

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.Safety of 1-(3-Bromopropyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary