522-57-6

Basic information

• Product Name: (6,7-dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone
• Synonyms: (6,7-dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone;papaveraldine;6,7-dimethoxy-1-veratroylisoquinoline;xanthaline;(6,7-Dimethoxyisoquinolin-1-yl)(3,4-dimethoxyphenyl) ketone;(6,7-dimethoxy-1-isoquinolyl)-(3,4-dimethoxyphenyl)methanone
• CAS NO: 522-57-6
• Molecular Formula: C₂₀H₁₉NO₅
• Molecular Weight: 353.36856
• EINECS: 208-331-4
• Mol File: 522-57-6.mol
• Article Data: 34

Chemical Properties

• Melting Point: 208-209°
• Boiling Point: 486.8°C (rough estimate)
• Flash Point: 279.1°C
• Appearance: /
• Density: 1.2976 (rough estimate)
• Vapor Pressure: 1.21E-11mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 2.04±0.40(Predicted)
• CAS DataBase Reference: (6,7-dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone(CAS DataBase Reference)
• NIST Chemistry Reference: (6,7-dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone(522-57-6)
• EPA Substance Registry System: (6,7-dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone(522-57-6)

Safety Data

• Hazardous Substances Data: 522-57-6(Hazardous Substances Data)

Usage

Uses

Papaveraldine is an impurity of Papaverine (P190500), a smooth muscle relaxant found in opium. Vasodilator (cerebral).

InChI:InChI=1/C20H19NO5/c1-23-15-6-5-13(10-16(15)24-2)20(22)19-14-11-18(26-4)17(25-3)9-12(14)7-8-21-19/h5-11H,1-4H3

Upstream product

• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 58-74-2 Papaverine 
• 71-43-2 benzene 
• 6957-27-3 3,4-dihydropapaverine 
• 50299-95-1 2-benzoyl-1-cyano-6,7-dimethoxy-1,2-dihydroisoquinoline 
• 20345-69-1 3,4-dihydropapaveraldine 
• 482-76-8 papaverinol 
• 17366-51-7 (Z)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 3947-79-3 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-3,4-dihydroisoquinolinium iodide 
• 61-25-6 papaverine hydrochloride 
• 83511-44-8 1-(2'-amino-4',5'-dimethoxy-α-oxobenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 13074-31-2 Tetrahydropapaverine 
• 7446-08-4 selenium(IV) oxide 

Downstream Products

• 861521-80-4 1-(3,4-dimethoxy-phenyl)-1-(7-hydroxy-6-methoxy-[1]isoquinolyl)-ethanol 
• 6152-76-7 6,7-dimethoxy-2-methyl-1-veratroyl-isoquinolinium; iodide 
• 15248-39-2 6,7-dimethoxyisoquinoline 
• 93-07-2 Veratric acid 
• 58-74-2 Papaverine 
• 20323-72-2 (6,7-dimethoxyisoquinolin-1-yl)(4,5-dimethoxy-2-nitrophenyl)-methanone 
• 482-76-8 papaverinol 
• 13074-31-2 Tetrahydropapaverine 
• 17656-58-5 (6,7-dimethoxy-isoquinolin-1-yl)-(3,4-dimethoxy-phenyl)-methanone oxime 
• 40766-58-3 1-(6,7-dimethoxy-isoquinolin-1-yl)-1-(3,4-dimethoxy-phenyl)-4-morpholin-4-yl-butan-1-ol 
• 58024-44-5 6,7-dimethoxy-1-(3',4'-dimethoxy-α-hydroxy-α-methylbenzyl)isoquinoline 
• 58024-46-7 (6,7-dimethoxyisoquinolin-1-yl)-(3,4-dimethoxyphenyl)phenylcarbinol 
• 91790-53-3 1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4-dimethoxybenzyl)isoquinoline 
• 58024-45-6 1-(6,7-dimethoxyisoquinolin-1-yl)-1-(3,4-dimethoxyphenyl)ethylene 

Relevant articles and documents

Hypervalent iodine oxidation products of papaverine and its microbial metabolites

(Diacetoxyiodo)benzene (DAIB) oxidizes papaverine to papaveraldine (2) and to 1-hydroxymethyl-6,7-dimethoxyisoquinoline (3), whereas 3'-desmethylpapaverine and 6-dexmethylpapaverine are converted into novel products (4) and (5), respectively.

Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis

A metal- and additive-free methodology for the highly selective, photocatalyzed C-H oxygenation of alkylarenes under air to the corresponding carbonyls is presented. The process is catalyzed by an imide-acridinium that forms an extremely strong photooxidant upon visible light irradiation, which is able to activate inert alkylarenes such as toluene. Hence, this is an easy to perform, sustainable and environmentally friendly oxidation that provides valuable carbonyls from abundant, readily available compounds.

Development of Pd(OAc)2-catalyzed tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds: Concise synthesis of 1-aroylisoquinoline, oxoaporphine, and 8-oxyprotoberberine alkaloids

A catalytic tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds is developed. This tandem oxidation is applied to two-step total syntheses of papaveraldine and pulcheotine A. Additionally, the total synthesis of liriodenine is achieved in six steps from homopiperonyl alcohol and 2-bromophenylacetonitrile by applying this catalytic tandem oxidation. Moreover, the direct conversion of xylopinine to 8-oxypseudopalmatine in a 76% yield demonstrates the versatility of this catalytic reaction.

Visible-Light-Mediated Direct Decarboxylative Acylation of Electron-Deficient Heteroarenes Using α-Ketoacids

Acylation of electron-deficient heteroaromatic compounds has been developed using visible light. α-Ketoacids have been used as an efficient source of acyl radicals under photoredox conditions. The in situ generated acyl radicals from α-ketoacids have been coupled to a wide variety of electron-deficient heteroaromatic compounds in a Minisci type reaction. This method would be attractive to access biologically attractive molecules.