158753-17-4

Basic information

• Product Name: 8-Amino-7-quinolinecarbaldehyde
• Synonyms: 8-Amino-7-quinolinecarbaldehyde;8-Aminoquinoline-7-carbaldehyde;8-Amino-7-quinolinecarboxaldehyde
• CAS NO: 158753-17-4
• Molecular Formula: C₁₀H₈N₂O
• Molecular Weight: 172.18332
• Mol File: 158753-17-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 381.363 °C at 760 mmHg
• Flash Point: 184.442 °C
• Appearance: /
• Density: 1.317
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.749
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.28±0.14(Predicted)
• CAS DataBase Reference: 8-Amino-7-quinolinecarbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Amino-7-quinolinecarbaldehyde(158753-17-4)
• EPA Substance Registry System: 8-Amino-7-quinolinecarbaldehyde(158753-17-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 158753-17-4(Hazardous Substances Data)

Usage

Chemical Properties

yellow powder

InChI:InChI=1/C10H8N2O/c11-9-8(6-13)4-3-7-2-1-5-12-10(7)9/h1-6H,11H2

Upstream product

• 101327-87-1 8-nitro-7-quinolinecarboxaldehyde 
• 7471-63-8 8-nitro-7-methylquinoline 
• 612-60-2 7-methylquinoline 
• 158753-15-2 8-trimethylacetamido-7-(1-propenyl)-quinoline 
• 176853-39-7 7-<β-trans-(N,N-dimethylamino)ethenyl>-8-nitroquinoline 
• 158753-16-3 8-trimethylacetamido-7-quinolinecarbaldehyde 

Downstream Products

• 1272029-49-8 2-(2',6'-difluorophenyl)-1,10-phenanthroline 
• 1853997-27-9 2-(1-bromonaphthalen-4-yl)-1,10-phenanthroline 
• 3002-77-5 2-methyl-1,10-phenanthroline 
• 1380049-28-4 2-(7-(4-nitrophenylethynyl)-9,9-dihexadecyl-fluoren-2-yl)-1,10-phenanthroline 
• 1380049-30-8 2-(7-(4-methoxyphenylethynyl)-9,9-dihexadecyl-fluoren-2-yl)-1,10-phenanthroline 
• 66-71-7 1,10-Phenanthroline 
• 109559-47-9 2-phenyl-1,10-phananthroline 

Relevant articles and documents

A Friedlaender approach to novel 1,10-phenanthrolines and their use as ligands for Ru(II) and Cu(I)

A six step synthesis of 8-amino-7-quinolinecarbaldehyde from 8-hydroxyquinoline has been developed. This aminoaldehyde undergoes Friedlaender condensation with ketones to form 2-substituted 1,10-phenanthrolines and 1,2-diketones to form 2,2′-bi-(1.10-phenanthroline)s. A tetramethylene derivative of the latter class of compounds forms a helical dinuclear complex with Cu(I).

Design and synthesis of chiral 1,10-phenanthroline ligand, and application in palladium catalyzed asymmetric 1,4-addition reactions

Pd-catalyzed asymmetric 1,4-addition of phenylboronic acid to α,β-unsaturated carbonyl compounds was developed using chiral 1,10-phenanthroline derivative as ligand. Good yields (up to 97%), and high enantioselectivities (up to 97% ee) were achieved.

Introduction of benzo[h]quinoline and 1,10-phenanthroline subunits by friedl?nder methodology

An improved preparation of 8-amino-7-quinolinecarbaldehyde has been developed. The methyl group of 7-methyl-8-nitroquinoline may be oxidized to an aldehyde by treatment first with dimethylformamide dimethyl acetal followed by sodium periodate. Reduction with iron provides the amino aldehyde. An analogous sequence affords 1-amino-2-naphthalenecarbaldehyde. Friedl?nder condensation of the quinoline derivative with a series of acetylaromatics provides the corresponding 2-aryl-1,10-phenanthrolines. Condensation of either amino aldehyde with 1,3-diacetylbenzene or 2,6-diacetylpyridine provides the expected Friedl?nder product. Similar chemistry is described for reactions of the amino aldehydes with 1,4-diacetylbenzene, 4,4′-diacetylbiphenyl, 1,5-diacetylanthracene, 1,2,3,4,5,6,7,8-octahydroacridine-1,8-dione, and tetracyclo-[6.3.0.0.4,1105,9]undecane-2,7-dione (TCU-2,7-dione).