877-42-9

Basic information

• Product Name: 6-Bromo-2-methylquinoline
• Synonyms: 6-BROMO-2-METHYLQUINOLINE;6-BROMOQUINALDINE;6-BROMOQUINAIDINE;6-Bromoquinaldine, 6-Bromo-2-methyl-1-azanaphthalene;6-BroMo-2-Methylquinoline, 97+%;Quinoline, 6-bromo-2-methyl-;6-Bromoquildine, 98%
• CAS NO: 877-42-9
• Molecular Formula: C₁₀H₈BrN
• Molecular Weight: 222.08
• EINECS: -0
• Product Categories: Quinoline&Isoquinoline;Alkylquinolines;Haloquinolines;Quinolines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;QuinolinesHeterocyclic Building Blocks
• Mol File: 877-42-9.mol

Chemical Properties

• Melting Point: 101-105 °C(lit.)
• Boiling Point: 299.7 °C at 760 mmHg
• Flash Point: 135 °C
• Appearance: white to light yellow crystal powder
• Density: 1.488 g/cm³
• Vapor Pressure: 0.00209mmHg at 25°C
• Refractive Index: 1.654
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 5.02±0.43(Predicted)
• CAS DataBase Reference: 6-Bromo-2-methylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromo-2-methylquinoline(877-42-9)
• EPA Substance Registry System: 6-Bromo-2-methylquinoline(877-42-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-42-36/37/38-20/21/22
• Safety Statements: 26-39-36/37/39-24/25-22
• WGK Germany: 3
• Hazardous Substances Data: 877-42-9(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

InChI:InChI=1/C10H8BrN/c1-7-2-3-8-6-9(11)4-5-10(8)12-7/h2-6H,1H3

Upstream product

• 872-36-6 vinylene carbonate 
• 106-40-1 4-bromo-aniline 
• 5332-25-2 6-bromoquinoline 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 6563-11-7 6-bromoquinoline-N-oxide 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 64-19-7 acetic acid 
• 109-92-2 ethyl vinyl ether 
• 64-17-5 ethanol 
• 123-42-2 4-Hydroxy-4-methyl-2-pentanone 
• 29124-57-0 2-amino-5-bromobenzaldehyde 
• 1080-92-8 6-bromo-4-ethoxy-2-methyl-1,2,3,4-tetrahydro-quinoline 
• 50-00-0 formaldehyd 
• 1253423-96-9 C₁₁H₁₁BrN₂O₅ 

Downstream Products

• 1315248-52-2 2-methyl-6-trimethylsilanylethynylquinoline 
• 1315248-45-3 tris(2-methylquinolin-6-yl)amine 
• 1196151-65-1 (6-bromoquinolin-2-yl)methanol 
• 1315248-43-1 6-bromo-2-{[(tert-butyldimethylsilyl)oxy]methyl}quinoline 
• 1315248-44-2 tris(2-{[(tert-butyldimethylsilyl)oxy]methyl}quinolin-6-yl)amine 
• 1233505-71-9 6-ethynyl-2-methylquinoline 
• 1315248-53-3 tris[4-(2-methylquinolin-6-ylethynyl)phenyl]amine 
• 1315248-54-4 tris[4-(2-formylquinolin-6-ylethynyl)phenyl]amine 
• 1315248-36-2 C₅₄H₃₆N₄O₃ 
• 1315248-46-4 tris(2-formylquinolin-6yl)amine 
• 1315248-40-8 [6,6',6''-nitrilotris(quinoline-6,2-diyl)]trimethanol 
• 1315248-34-0 [6,6',6''-nitrilotris(quinoline-6,2-diyl)]tris(methylene) triacetate 
• 1542158-19-9 4-((6-bromoquinolin-2-yl)methyl)chroman-2-one 
• 1542158-35-9 4-((6-bromoquinolin-2-yl)methyl)thiochroman-2-one 

Relevant articles and documents

Imaging of formaldehyde fluxes in epileptic brains with a two-photon fluorescence probe

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Rhodium-Catalyzed C-H Annulation of Free Anilines with Vinylene Carbonate as a Bifunctional Synthon

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Cooperative Lewis Acid Catalysis for the Enantioselective C(sp3)-H Bond Functionalizations of 2-Alkyl Azaarenes

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ZnMe2-Mediated, Direct Alkylation of Electron-Deficient N-Heteroarenes with 1,1-Diborylalkanes: Scope and Mechanism

The regioselective, direct alkylation of electron-deficient N-heteroarenes is, in principle, a powerful and efficient way of accessing alkylated N-heteroarenes that are important core structures of many biologically active compounds and pharmaceutical agents. Herein, we report a ZnMe2-promoted, direct C2- or C4-selective primary and secondary alkylation of pyridines and quinolines using 1,1-diborylalkanes as alkylation sources. While substituted pyridines and quinolines exclusively afford C2-alkylated products, simple pyridine delivers C4-alkylated pyridine with excellent regioselectivity. The reaction scope is remarkably broad, and a range of C2- or C4-alkylated electron-deficient N-heteroarenes are obtained in good yields. Experimental and computational mechanistic studies imply that ZnMe2 serves not only as an activator of 1,1-diborylalkanes to generate (α-borylalkyl)methylalkoxy zincate, which acts as a Lewis acid to bind to the nitrogen atom of the heterocycles and controls the regioselectivity, but also as an oxidant for rearomatizing the dihydro-N-heteroarene intermediates to release the product.

Nickel-Catalyzed Dehydrogenation of N-Heterocycles Using Molecular Oxygen

Herein, an efficient and selective nickel-catalyzed dehydrogenation of five- and six-membered N-heterocycles is presented. The transformation occurs in the presence of alkyl, alkoxy, chloro, free hydroxyl and primary amine, internal and terminal olefin, trifluoromethyl, and ester functional groups. Synthesis of an important ligand and the antimalarial drug quinine is demonstrated. Mechanistic studies revealed that the cyclic imine serves as the key intermediate for this stepwise transformation.

Synthesis and biological evaluation of 2-quinolineacrylamides

A series of C6-substituted N-hydroxy-2-quinolineacrylamides (3–15), with four types of bridging groups have been synthesized. Most of these compounds exhibit antiproliferative activity against A549 and HCT116 cells and Western blot analysis revealed that they are able to inhibit HDAC. Measurement of the HDAC isoform activity of ether-containing compounds showed that compound 9 has distinct HDAC6 selectivity, more than 300-fold over other isoforms. This paper describes the development of 6-aryloxy-N-hydroxy-2-quinolineacrylamides as potential HDAC6 inhibitors.

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