22493-93-2

Basic information

• Product Name: 2-sec-Butylquinoline
• Synonyms: 2-sec-Butylquinoline
• CAS NO: 22493-93-2
• Molecular Formula: C13H15N
• Molecular Weight: 0
• Mol File: 22493-93-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-sec-Butylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-sec-Butylquinoline(22493-93-2)
• EPA Substance Registry System: 2-sec-Butylquinoline(22493-93-2)

Safety Data

• Hazardous Substances Data: 22493-93-2(Hazardous Substances Data)

Upstream product

• 860719-98-8 2-sec-butyl-1-methyl-1,2-dihydro-quinoline 
• 91-22-5 quinoline 
• 598-30-1 sec.-butyllithium 
• 18936-17-9 2-methylbutanenitrile 
• 103-63-9 1-phenyl-2-bromoethane 
• 3947-76-0 N-methylquinolinium iodide 
• 5344-90-1 2-Aminobenzyl alcohol 
• 565-61-7 3-methyl-pentan-2-one 
• 75164-10-2 2-lithioquinoline 
• 1113-78-6 tri(sec-butyl)borane 
• 53317-06-9 B-sec-butyl-9-borabicyclo<3.3.1>nonane 

Relevant articles and documents

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.

A rhodium-catalyzed route for oxidative coupling and cyclization of 2-aminobenzyl alcohol with ketones leading to quinolines

2-Aminobenzyl alcohol undergoes oxidative cyclization with aryl(alkyl), alkyl(alkyl) and cyclic ketones in dioxane at 80° in the presence of a catalytic amount of RhCl(PPh3)3 along with KOH to afford the corresponding quinolines in good yields. The catalytic pathway seems to be proceeded via a sequence involving initial oxidation of 2-aminobenzyl alcohol to 2-aminobenzaldehyde by a rhodium catalyst, cross aldol reaction between 2-aminobenzaldehyde and ketones, and cyclodehydration.

REACTIONS OF TRIALKYL(2- or 4-QUINOLYL)BORATES

Reactions of trialkyl(2-quinolyl)borates and trialkyl(4-quinolyl)borates were investigated.