24331-94-0

Basic information

• Product Name: 1,4-Dihydro-3(2H)-isoquinolinone
• Synonyms: 1,4-DIHYDRO-3(2H)-ISOQUINOLINONE;1,4-DIHYDRO-2H-ISOQUINOLIN-3-ONE;3(2H)-Isoquinolinone, 1,4-dihydro-;1,2,3,4-Tetrahydroisoquinolin-3-one;1,2-Dihydroisoquinoline-3(4H)-one;1,4-dihydroisoquinolin-3(2H)-one;1,2-dihydroisoquinolin-3(4H)-one
• CAS NO: 24331-94-0
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• EINECS: 246-174-3
• Product Categories: pharmacetical
• Mol File: 24331-94-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 146-148 °C
• Boiling Point: 370.61 °C at 760 mmHg
• Flash Point: 215.874 °C
• Appearance: /
• Density: 1.143 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 16.35±0.20(Predicted)
• CAS DataBase Reference: 1,4-Dihydro-3(2H)-isoquinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dihydro-3(2H)-isoquinolinone(24331-94-0)
• EPA Substance Registry System: 1,4-Dihydro-3(2H)-isoquinolinone(24331-94-0)

Safety Data

• Hazardous Substances Data: 24331-94-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 107, p. 435, 1985 DOI: 10.1021/ja00288a027

InChI:InChI=1/C9H9NO/c11-9-5-7-3-1-2-4-8(7)6-10-9/h1-4H,5-6H2,(H,10,11)

Upstream product

• 615-13-4 2-indanone 
• 21151-64-4 N,N'-methylenebis(2-phenylacetamide) 
• 94286-13-2 (2-aminomethyl-phenyl)-acetic acid ethyl ester 
• 50-00-0 formaldehyd 
• 103-81-1 Benzeneacetamide 
• 100-46-9 benzylamine 
• 63969-83-5 2-formylphenylacetic acid methyl ester 
• 119-65-3 isoquinoline 
• 56023-50-8 methyl 2-(2-azidomethyl)phenyl acetate 
• 79388-18-4 N-Benzyl-2-methanesulfinyl-acetamide 
• 18813-51-9 Methylmercaptoessigsaeure-benzylamid 
• 138350-83-1 N-(tert-butoxycarbonyl)-2-methylbenzylamine 
• 57058-32-9 N-(2-chlorobenzyl)acetamide 
• 428501-02-4 ethyl 2-(2-(azidomethyl)phenyl)acetate 

Downstream Products

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 122101-06-8 4-benzyl-1,4-dihydroisoquinolin-3(2H)-one 
• 6772-73-2 1,4-dihydro-2-(phenylmethyl)-3(2H)-isoquinolinone 
• 4370-95-0 3-amino-2-phenyl-propionic acid 
• 122101-04-6 4-Benzyl-1,4-dihydro-2-methyl-3(2H)-isochinolinon 
• 143265-93-4 3-ethoxy-4-methyl-1H-2-benzazepine 
• 143265-98-9 3-ethoxy-5-methyl-1H-2-benzazepine 
• 143266-13-1 4,5-dimethyl-3-ethoxy-1H-2-benzazepine 
• 143265-95-6 3-ethoxy-1,4-dihydro-4-hydroxymethyl-4-methylisoquinoline 
• 146645-31-0 4-Benzyl-3,3-dideutero-2-methyl-1,2,3,4-tetrahydroisochinolin 
• 143266-06-2 4-benzoyl-3-ethoxy-1,4-dihydro-4-methylisoquinoline 
• 120285-29-2 3-chloroisoquinoline-4-carbaldehyde 
• 103681-65-8 1,2-Diphenyl-3-oxo-3H,5H-pyrrolo<1,2-b>isochinolin 
• 103681-57-8 3,5-Dioxo-1,2-diphenyl-3H,5H-pyrrolo<1,2-b>isochinolin 

Relevant articles and documents

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The Synthesis of N-Heterocycles using ortho-Metallated Primary Benzylamine Complexes of Palladium(II) and Platinum(II)

The synthesis of the isoindolinimines (5) by the insertion of isocyanides into the metal-carbon bond of the ortho-palladated primary benzylamine complex (1a) is described; the novel oxidative addition and subsequent reductive elimination of the ortho-metallated primary benzylamine-platinum complex (6) yields 3-oxo-1,2,3,4-tetrahydroisoquinoline (8).

Rapid and Mild Lactamization Using Highly Electrophilic Triphosgene in a Microflow Reactor

Lactams are cyclic amides that are indispensable as drugs and as drug candidates. Conventional lactamization includes acid-mediated and coupling-agent-mediated approaches that suffer from narrow substrate scope, much waste, and/or high cost. Inexpensive, less-wasteful approaches mediated by highly electrophilic reagents are attractive, but there is an imminent risk of side reactions. Herein, a methods using highly electrophilic triphosgene in a microflow reactor that accomplishes rapid (0.5–10 s), mild, inexpensive, and less-wasteful lactamization are described. Methods A and B, which use N-methylmorpholine and N-methylimidazole, respectively, were developed. Various lactams and a cyclic peptide containing acid- and/or heat-labile functional groups were synthesized in good to high yields without the need for tedious purification. Undesired reactions were successfully suppressed, and the risk of handling triphosgene was minimized by the use of microflow technology.

Desymmetrization of Prochiral Cyclopentenes Enabled by Enantioselective Palladium-Catalyzed Oxidative Heck Reaction

In the presence of a catalytic amount of Pd(TFA)2 and a chiral Pyox ligand under oxygen atmosphere, oxidative Heck reaction between arylboronic acids and 4-substituted or 4,4-disubstituted cyclopent-1-enes afforded the chiral arylated products with concurrent creation of two stereocenters in good yields with excellent diastereo- and enantioselectivities.