Category: 178396-31-1

Safety of 6-Bromo-8-methylquinoline. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 6-Bromo-8-methylquinoline, is researched, Molecular C10H8BrN, CAS is 178396-31-1, about Ru(II)-Catalyzed Chemoselective C(sp3)-H Monoarylation of 8-Methyl Quinolines with Arylboronic Acids. Author is Parmar, Diksha; Kumar, Rohit; Kumar, Rakesh; Sharma, Upendra.

The first [Cl2Ru(p-cymene)]2-catalyzed direct mono-arylation of unactivated C(sp3)-H bond of 8-Me quinolines with aryl boronic acids to synthesize 8-benzyl quinolines I [R = 2-Me, 7-Br, 5-NO2, etc.; R1 = 2-FC6H4, 4-ClC6H4, 4-MeOC6H4, etc.] was presented. The transformation showed broad substrate substrate scope with high chemoselectivity for the synthesis of 8-benzyl quinolines. In preliminary mechanistic study- control experiments, deuterium labeling experiments and kinetic studies had been performed.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Some derivatives of 6-bromo-8-methylquinoline and 6-chloro-8-methylquinoline》. Authors are Irving, Thurman A.; Greene, Joseph L. Jr.; Peterson, Joe G.; Capps, Julius D..The article about the compound:6-Bromo-8-methylquinolinecas:178396-31-1,SMILESS:CC1=CC(Br)=CC2=C1N=CC=C2).Recommanded Product: 178396-31-1. Through the article, more information about this compound (cas:178396-31-1) is conveyed.

cf. C.A. 44, 9965f. 6-Chloro-8-methylquinoline picrate m. 223-4°. 2-Acetamido-5-bromo-4-nitrotoluene (I), m. 153-4°; the Cl analog m. 142-3° [Reverdin and Crepieux, Ber. 33, 2505(1900), gave 262°]. Skraup ring closure of 8 g. I gives 1.9 g. 6-bromo-8-methyl-5-nitroquinoline (II), m. 117-18°; 6-Cl analog (III), m. 99-100°, 9.3%. By the previous method, II yields 76% crude 6-bromo-1,8-dimethyl-2(1H)-quinolone (IV), m. 76-81°, which with POCl3-PCl5 gives 76% 6-bromo-2-chloro-8-methylquinoline (V), m. 120-1°; 6-Cl analog of IV, m. 64-5°, 75%; 6-Cl analog (VI) of V, m. 121-2°, 78%. V (2 g.) in 25% (by volume) H2SO4, heated 2 h. at 175-80° (autoclave), gives 84% 6-bromo-2-hydroxy-8-methylquinoline, m. 280-1°; 6-Cl analog (9.1 g. from 10 g. VI), m. 265-6°. I (25 g.) and 20 mL. Me2SO4, heated 1 h. at 150-70° and 1.5 h. at 145° and oxidized with 30% H2O2 at 55-65°, give 65% 6-bromo-1,8-dimethyl-5-nitroquinolone (VII), m. 158-9°; crude Cl analog, m. 121-2° (decomposition). VII yields 69% 2,6-dibromo-8-methyl-5-nitro-2(1H)-quinoline, m. 160-1°; 2,6-di-Cl compound, m. 137-8°, 73%. 6-Bromo-2-hydroxy-8-methyl-5-nitroquinoline, m. 311-12°, 87%; 6-Cl analog, m. 271-2°. Reduction in Me2CO or absolute EtOH over Raney Ni gives the following: 5-amino-6-bromo-8-methylquinoline, m. 116-17°, 73% (Ac derivative, m. 235-6°, 81%; Bz derivative, m. 210-11°, 69%); 6-Cl analog, m. 113-14°, 92% (Ac derivative, m. 225-6°, 82%; Bz derivative, m. 193-4°, 79%); 5-amino-2-chloro-6-bromo-8-methylquinoline, m. 127-8° (6 g. from 10 g. NO2 compound) (Ac derivative, m. 272-3°, 84%; Bz derivative, m. 252-3°, 60%); 5-amino-2,6-dichloro-8-methylquinoline, m. 132-3°, 96% (Ac derivative, m. 265-6°, 84%; Bz derivative, m. 253-4°, 65%); 5-amino-2-hydroxy-6-bromo-8-methylquinoline, m. 238-9°, 89% [Ac derivative, m. 318-19° (decomposition); Bz derivative, m. 297-8°, 75%]; 5-amino-2-hydroxy-6-chloro-8-methylquinoline (Ac derivative, m. above 340°, 54%; Bz derivative, m. 331-2°, 93%). By the Bart reaction (cf. Capps and Hamilton, C.A. 32, 8421.4) were prepared: 6-bromo-8-methyl-5-quinoline arsonic acid, m. 244-5° (decomposition), 10.5%; 6-Cl analog, m. 255-6°, 17%; 2-chloro-6-bromo analog, m. above 330°, 7.7%; 2,6-di-Cl compound, m. 302-3°, 6.7%; 2-hydroxy-6-bromo analog, m. above 330°, 8.8%; 2-hydroxy-6-chloro analog, m. 325-6°, 6.5%.

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Barsu, Nagaraju; Rahman, Atiur Md.; Sen, Malay; Sundararaju, Basker published the article 《Cp*CoIII-Catalyzed C(sp3)-H Bond Amidation of 8-Methylquinoline》. Keywords: quinolinylmethylamide preparation; methylquinoline oxazolone amidation cobalt catalyst; amidation; cobalt; quinoline; sp3 C−H activation.They researched the compound: 6-Bromo-8-methylquinoline( cas:178396-31-1 ).Quality Control of 6-Bromo-8-methylquinoline. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:178396-31-1) here.

An efficient and external oxidant-free, Cp*CoIII-catalyzed C(sp3)-H bond amidation of 8-methylquinoline, using oxazolone as an efficient amidating agent, is reported for the first time under mild conditions. The reaction is selective and tolerates a variety of functional groups. Based on previous reports and exptl. results, the deprotonation pathway proceeds through an external base-assisted concerted metalation and deprotonation process.

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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 6-Bromo-8-methylquinoline( cas:178396-31-1 ) is researched.Recommanded Product: 6-Bromo-8-methylquinoline.Kumar, Rohit; Kumar, Rakesh; Parmar, Diksha; Gupta, Shiv Shankar; Sharma, Upendra published the article 《Ru(II)/Rh(III)-Catalyzed C(sp3)-C(sp3) Bond Formation through C(sp3)-H Activation: Selective Linear Alkylation of 8-Methylquinolines and Ketoximes with Olefins》 about this compound( cas:178396-31-1 ) in Journal of Organic Chemistry. Keywords: alkylquinoline alkylsantonin oxime regioselective preparation; ruthenium rhodium catalyst regioselective alkylation methylquinoline acrylate styrene alkene; regioselective alkylation methylquinoline santonin oxime ether alkene ruthenium catalyst; rhodium catalyst regioselective alkylation methylquinoline santonin oxime ether alkene; mechanism kinetic isotope effect regioselective alkylation methylquinoline acrylate. Let’s learn more about this compound (cas:178396-31-1).

In the presence of either [RuCl2(p-cymene)]2 or [Cp*RhCl2]2 and AgSbF6, 8-methylquinolines underwent regioselective alkylation with acrylates, styrenes, and other alkenes mediated by pivalic acid in hexafluoroisopropanol to yield 8-alkylquinolines with linear alkyl substituents. The mechanism of the reaction was studied using deuterium labeling, kinetic isotope effect, and competition studies; the reaction may proceed through a five-membered metallacycle intermediate. Under similar conditions, an O-methyloxime derivative of (-)-santonin underwent regioselective alkylation with Et acrylate and acrylonitrile.

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Yu, Songjie; Tang, Guodong; Li, Yingzi; Zhou, Xukai; Lan, Yu; Li, Xingwei published an article about the compound: 6-Bromo-8-methylquinoline( cas:178396-31-1,SMILESS:CC1=CC(Br)=CC2=C1N=CC=C2 ).Product Details of 178396-31-1. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:178396-31-1) through the article.

Previous direct C-H nitrogenation suffered from simple amidation/amination with limited atom-economy and is mostly limited to C(sp2)-H substrates. In this work, anthranil was designed as a novel bifunctional aminating reagent for both C(sp2)-H and C(sp3)-H bonds under rhodium(III) catalysis, thus affording a nucleophilic aniline tethered to an electrophilic carbonyl, e. g., I. A tridendate rhodium(III) complex has been isolated as the resting state of the catalyst, and DFT studies established the intermediacy of a nitrene species.

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