23687-25-4

Basic information

• Product Name: 4-Isoquinolinamine
• Synonyms: isoquinolin-4-amine; Isoquinolin-4-amine
• CAS NO: 23687-25-4
• Molecular Formula: C₉H₈N₂
• Molecular Weight: 144.1732
• EINECS: 245-823-8
• Product Categories: wq;Building Blocks;Isoquinoline;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Quinoline series;Amines;Quinolines, Isoquinolines & Quinoxalines;Quinolines, Isoquinolines & Quinoxalines
• Mol File: 23687-25-4.mol
• Article Data: 18

Chemical Properties

• Melting Point: 108.0 to 112.0 °C
• Boiling Point: 360 °C at 760 mmHg
• Flash Point: 198.9 °C
• Appearance: /
• Density: 1.21 g/cm³
• Vapor Pressure: 2.29E-05mmHg at 25°C
• Refractive Index: 1.708
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 6.29±0.10(Predicted)
• CAS DataBase Reference: 4-Isoquinolinamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Isoquinolinamine(23687-25-4)
• EPA Substance Registry System: 4-Isoquinolinamine(23687-25-4)

Safety Data

• Hazard Codes: Xi:
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 23687-25-4(Hazardous Substances Data)

Usage

Uses

4-Isoquinolylamine can be used for synthesis of Rho kinase inhibitors.

Synthesis Reference(s)

Journal of the American Chemical Society, 64, p. 783, 1942 DOI: 10.1021/ja01256a012

InChI:InChI=1/C9H8N2/c10-9-6-11-5-7-3-1-2-4-8(7)9/h1-6H,10H2

Upstream product

• 1532-97-4 4-bromoisoquinoline 
• 1532-91-8 4-chloroisoquinoline 
• 881668-81-1 N-benzylisoquinolin-4-amine 
• 36073-93-5 4-nitro-isoquinoline 
• 20377-03-1 4-azidoisoquinoline 
• 75-08-1 ethanethiol 
• 1421429-90-4 N-(diphenylmethylene)-isoquinolin-4-amine 

Downstream Products

• 136849-93-9 4-acetamidoisoquinoline 
• 681448-78-2 N-(isoquinolin-4-yl)benzamide 
• 857622-00-5 N-acetyl-sulfanilic acid-[4]isoquinolylamide 
• 130831-67-3 5,6,7,8-tetrahydro-[4]isoquinolylamine 
• 1421428-70-7 1-((2-(cyclohexylthio)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(isoquinolin-4-yl)urea 
• 1145753-88-3 tert-butyl 4-amino-3,4-dihydro-1H-isoquinoline-2-carboxylate 
• 881668-81-1 N-benzylisoquinolin-4-amine 

Relevant articles and documents

Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides

The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.

Nickel-catalyzed monoarylation of ammonia

Structurally diverse (hetero)aryl chloride, bromide, and tosylate electrophiles were employed in the Ni-catalyzed monoarylation of ammonia, including chemoselective transformations. The employed JosiPhos/[Ni(cod)2] catalyst system enables the use of commercially available stock solutions of ammonia, or the use of ammonia gas in these reactions, thereby demonstrating the versatility and potential scalability of the reported protocol. Proof-of-principle experiments established that air-stable [(JosiPhos)NiCl2] precatalysts can be employed successfully in such transformations. Lighten Up: The substrate scope of the title reaction includes (hetero)aryl chloride, bromide, and tosylate electrophiles. The versatility and potential scalability of the reported method is demonstrated by the use of either commercially available stock solutions of ammonia or ammonia gas.

Assembly of Primary (Hetero)Arylamines via CuI/Oxalic Diamide-Catalyzed Coupling of Aryl Chlorides and Ammonia

A general and practical catalytic system for aryl amination of aryl chlorides with aqueous or gaseous ammonia has been developed, with CuI as the catalyst and bisaryl oxalic diamides as the ligands. The reaction proceeds at 105-120°C to provide a diverse set of primary (hetero)aryl amines in high yields with various functional groups.