1-Oxo-1,2-dihydroisoquinoline-4-carbaldehyde

Base Information

• Chemical Name: 1-Oxo-1,2-dihydroisoquinoline-4-carbaldehyde
• CAS No.: 63125-40-6
• Molecular Formula: C₁₀H₇NO₂
• Molecular Weight: 173.171
• Hs Code.: 2933790090
• DSSTox Substance ID: DTXSID80591784
• Nikkaji Number: J2.556.471E
• Wikidata: Q72498668
• Mol file: 63125-40-6.mol

Synonyms:1-OXO-1,2-DIHYDROISOQUINOLINE-4-CARBALDEHYDE;63125-40-6;1-oxo-2H-isoquinoline-4-carbaldehyde;1-Hydroxyisoquinoline-4-carbaldehyde;SCHEMBL4826183;DTXSID80591784;NQYUPIHTJCUWKA-UHFFFAOYSA-N;AKOS015898990;DB-011876;A8712;1-oxo-1,2-dihydro-isoquinoline-4-carbaldehyde;1-oxo-1,2-dihydroisoquinoline-4-carboxaldehyde;EN300-319057

Chemical Property of 1-Oxo-1,2-dihydroisoquinoline-4-carbaldehyde

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 235-238 °C
• Refractive Index: 1.685
• Boiling Point: 453.66 °C at 760 mmHg
• Flash Point: 218.262 °C
• PSA: 49.93000
• Density: 1.367 g/cm³
• LogP: 1.34060
• Storage Temp.: 2-8°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 173.047678466
• Heavy Atom Count: 13
• Complexity: 270

Purity/Quality:

99% ^*data from raw suppliers

1-Oxo-1,2-dihydroisoquinoline-4-carbaldehyde 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CNC2=O)C=O

Technology Process of 1-Oxo-1,2-dihydroisoquinoline-4-carbaldehyde

There total 4 articles about 1-Oxo-1,2-dihydroisoquinoline-4-carbaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

4-bromo-1,2-dihydroisoquinolin-1-one (3951-95-9) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 1,2-dihydro-1-oxo-4-isoquinolinecarboxaldehyde (63125-40-6)

Guidance literature:

4-bromo-1,2-dihydroisoquinolin-1-one; With methyllithium; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.166667h;

With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane; at -78 ℃; for 0.5h;

N,N-dimethyl-formamide; In tetrahydrofuran; diethyl ether; hexane; at -78 ℃; for 1h; Further stages.;

DOI:10.1080/00397910701575343

Reference yield: 23.0%

2-(1-((tert-butyldimethylsilyl)oxy)-3-(trimethylsilyl)prop-2-yn-1-yl)benzonitrile → 1,2-dihydro-1-oxo-4-isoquinolinecarboxaldehyde (63125-40-6)

Guidance literature:

With 2,6-dichloropyridine N-oxide; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); water; zinc trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 100 ℃; for 1h; Inert atmosphere; Sealed tube;

DOI:10.1039/d0cc06875f

Reference yield:

1-methoxy-4-isoquinolinecarboxaldehyde (1005772-69-9) → 1,2-dihydro-1-oxo-4-isoquinolinecarboxaldehyde (63125-40-6)

Guidance literature:

With hydrogen bromide; at 25 ℃; for 16h;

DOI:10.1080/00397910701575343

upstream raw materials:

1-methoxy-4-isoquinolinecarboxaldehyde

4-bromo-1,2-dihydroisoquinolin-1-one

N,N-dimethyl-formamide

Refernces

• 1、 Sercel, Anthony D.,Sanchez, Joseph P.,Showalter, H. D. Hollis. "Simple synthesis of 4-substituted 1(2H)-isoquinolinones via electrophilic trapping of lithiated mono- and dianion precursors". . p. 4199 - 4208. Retrieved 2008/03/13.