178396-31-1

Basic information

• Product Name: 8-methyl-6-bromoquinoline
• Synonyms: 8-methyl-6-bromoquinoline;6-bromo-8-methylquinoline
• CAS NO: 178396-31-1
• Molecular Formula: C₁₀H₈BrN
• Molecular Weight: 222.08
• EINECS: -0
• Mol File: 178396-31-1.mol

Chemical Properties

• Appearance: /
• Density: 1.488
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 8-methyl-6-bromoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 8-methyl-6-bromoquinoline(178396-31-1)
• EPA Substance Registry System: 8-methyl-6-bromoquinoline(178396-31-1)

Safety Data

• Hazardous Substances Data: 178396-31-1(Hazardous Substances Data)

Usage

Chemical Properties

yellow powder

Upstream product

• 120-66-1 N-(2-methylphenyl)acetamide 
• 56-81-5 glycerol 
• 583-75-5 4-Bromo-2-methylaniline 

Downstream Products

• 926207-02-5 6-bromo-8-bromomethylquinoline 
• 1609646-76-5 N-((6-bromoquinolin-8-yl)methyl)-4-(trifluoromethyl)benzenesulfonamide 
• 854834-69-8 5-amino-6-bromo-8-methyl-quinolin-2-ol 
• 858467-33-1 6-bromo-2-chloro-8-methyl-[5]quinolylamine 
• 50358-36-6 6-bromo-8-methyl-[5]quinolylamine 
• 99465-08-4 6-bromo-8-methyl-quinolin-2-ol 
• 99455-14-8 6-Bromo-2-chloro-8-methylquinoline 
• 954563-85-0 6-bromo-8-methyl-1,2,3,4-tetrahydro-quinoline 
• 75908-52-0 6-bromo-8-methyl-5-nitro-quinoline 

Relevant articles and documents

RhIII-Catalyzed Direct Heteroarylation of C(sp3)-H and C(sp2)-H Bonds in Heterocycles with N-Heteroaromatic Boronates

Herein, we disclose a RhIII-catalyzed heteroarylation of C(sp3)-H and C(sp2)-H bonds in heterocycles with organoboron reagents. This protocol displays high efficiency and excellent functional group tolerance. A range of heterocyclic boronates with strong coordinating atoms, including pyridine, pyrimidine, pyrazole, thiophene, and furan derivatives, can be extensively served as the coupling reagents. The direct heteroarylation method could supply potential application in terms of the synthesis of drug molecules with multiple heterocycles.

Rhodium(III)-Catalyzed Direct Coupling of Quinoline-8-Carbaldehydes with (Het)Arylboronic Acids for the Synthesis of 8-Aryloylquinolines

Herein, we describe a method for the synthesis of aryl-(het)aryl ketones by Rh(III)-catalyzed direct coupling between quinoline-8-carbaldehydes and (het)arylboronic acids. The method has a broad substrate scope, a high functional group tolerance, and uses

Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C-H Activation

The rhodium(III)-catalyzed coupling of C-H substrates with iodonium ylides has been realized for the efficient synthesis of diverse cyclic skeletons, where the iodonium ylides have been identified as efficient and outstanding carbene precursors. The reaction systems are applicable to both sp2 and sp3 C-H substrates under mild and redox-neutral conditions. The catalyst loading can be as low as 0.5 mol % in a gram-scale reaction. Representative products exhibit cytotoxicity toward human cancer cells at nanomolar levels.

Cp?Rh(III)-Catalyzed Mild Addition of C(sp3)-H Bonds to α,β-Unsaturated Aldehydes and Ketones

A Rh(III)-catalyzed addition of benzylic C(sp3)-H bond to α,β-unsaturated ketones/aldehydes has been realized, leading to efficient synthesis of γ-aryl ketones/aldehydes. This atom-economic reaction proceeded under mild and redox-neutral conditions with a broad substrate scope. Besides benzylic C-H, allylic C-H bonds are also applicable when assisted by O-methyl ketoxime directing groups.

Rh-Catalyzed Direct Amination of Unactivated C(sp3)?H bond with Anthranils Under Mild Conditions

C?N Bond formation is of great significance due to the ubiquity of nitrogen-containing compounds. Here, a mild and efficient RhIII-catalyzed C(sp3)?H aryl amination reaction is reported. Anthranil is employed as the nitrogen source with 100 % atom efficiency. This C?H amination reaction exhibits broad substrate scope without using any external oxidants. Mechanistic studies including rhodacycle intermediates, H–D exchange, kinetic isotope effect (KIE) experiments, and in situ IR are presented.

Rhodium(III)-catalyzed intermolecular amidation with azides via C(sp 3)-H functionalization

The amidation reactions of 8-methylquinolines with azides catalyzed by a cationic rhodium(III) complex proceed efficiently to give quinolin-8- ylmethanamine derivatives in good yields via C(sp3)-H bond activation under external oxidant-free conditions. A catalytically competent five-membered rhodacycle has been isolated and characterized, revealing a key intermediate in the catalytic cycle.

Substituted Heterocyclic Ethers and Their Use in CNS Disorders

The invention encompasses compounds of Formula I, including pharmaceutically acceptable salts, their pharmaceutical compositions, and their use in treating CNS disorders.