30465-68-0

Basic information

• Product Name: 5-METHOXYQUINOLIN-8-AMINE
• Synonyms: 8-AMINO-5-METHOXYQUINOLINE;5-METHOXYQUINOLIN-8-AMINE;5-METHOXY-QUINOLIN-8-YLAMINE;8-QuinolinaMine, 5-Methoxy-;5-methoxy-8-aminoquinoline;8-Amino-5-methoxyquinoline 95%
• CAS NO: 30465-68-0
• Molecular Formula: C₁₀H₁₀N₂O
• Molecular Weight: 174.2
• Product Categories: organic building block
• Mol File: 30465-68-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 90-95°C
• Boiling Point: 355.7 °C at 760 mmHg
• Flash Point: 168.9 °C
• Appearance: /
• Density: 1.217 g/cm³
• Vapor Pressure: 3.06E-05mmHg at 25°C
• Refractive Index: 1.664
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 3.98±0.12(Predicted)
• CAS DataBase Reference: 5-METHOXYQUINOLIN-8-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXYQUINOLIN-8-AMINE(30465-68-0)
• EPA Substance Registry System: 5-METHOXYQUINOLIN-8-AMINE(30465-68-0)

Safety Data

• Hazardous Substances Data: 30465-68-0(Hazardous Substances Data)

Usage

Uses

The Chen auxiliary was reported to be an effective directing group in the synthesis of pyrrolidones from assisting in the activation of C(sp3)-H bonds and can be readily installed through amide bond formation and removed through mild conditions using CAN at room temperature.

General Description

8-Amino-5-methoxyquinoline is a substituted quinoline derivative that can be prepared using 5-chloro-2-nitroaniline as a starting material. It can act as an easily removable directing group and also mediate C-H activation. These properties have been useful for synthesizing isomeric dibenzoxazepinones and complex pyrrolidinones from compounds containing 8-amino-5-methoxyquinoline moiety.

InChI:InChI=1/C10H10N2O/c1-13-9-5-4-8(11)10-7(9)3-2-6-12-10/h2-6H,11H2,1H3

Upstream product

• 6942-98-9 5-chloro-8-nitroquinoline 
• 578-66-5 8-amino quinoline 
• 33757-47-0 N-(quinolin-8-yl)butyramide 
• 1635-61-6 5-chloro-2-nitroaniline 
• 36020-53-8 6-methoxy-8-nitroquinoline 

Downstream Products

• 1604839-65-7 N-(5-methoxyquinolin-8-yl)benzamide 

Relevant articles and documents

Systematic ligand variation to modulate the electrochemical properties of iron and manganese complexes

A series of iron(+iii) and manganese(+ii) complexes based on the dpaqR-ligand system (dpaq = 2-[bis(pyridine-2-ylmethyl)]amino-N-quinolin-8-yl-acetamide) were investigated using cyclic voltammetry (CV) to elucidate how the electronic properties of the ligands influence the overpotential and catalytic current in the context of water oxidation catalysis. For the Fe-complexes an electron withdrawing NO2 or CF3 group attached to the 5-position of the quinoline unit increased the catalytic current, but only with a simultaneous increase of the overpotential. However, when a pyrene moiety was attached to the dipicolylamine unit of the ligand, the overpotential decreased with concomitant increase of the catalytic current. Although the manganese complexes showed no reversible formation of a molecular catalytically active species for water oxidation, the variations of the ligand scaffold affected largely the same trends in their electrochemical behavior.

Auxiliary-Directed C(sp3)?H Arylation by Synergistic Photoredox and Palladium Catalysis

Herein we describe the auxiliary-directed arylation of unactivated C(sp3)?H bonds with aryldiazonium salts, which proceeds under synergistic photoredox and palladium catalysis. The site-selective arylation of aliphatic amides with α-quaternary centres is achieved with high selectivity for β-methyl C(sp3)?H bonds. This operationally simple method is compatible with carbocyclic amides, a range of aryldiazonium salts and proceeds at ambient conditions.

Auxiliary-assisted palladium-catalyzed halogenation of unactivated C(sp3)-H bonds at room temperature

The direct transformation of unactivated C(sp3)-H bonds into C-halogen bonds was achieved by palladium catalysis at room temperature with good functional group tolerance. Some drugs and natural products were readily modified by this method. Merged with substitution reaction, newly formed C-X bonds can be transformed into diverse C-O, C-S, C-C and C-N bonds. A preliminary mechanism study demonstrates that solvent is crucial for C-H activation and the C-H activation step is involved in the rate-limiting step. An isolated Pd(ii) intermediate can be transformed into a halogenated product with the retention of conformation which suggests that concerted reductive elimination from Pd(iv) to form a C-X bond was favored.