2-Amino-1,2,3,4-tetrahydroisoquinoline-1,3-dione

Base Information

• Chemical Name: 2-Amino-1,2,3,4-tetrahydroisoquinoline-1,3-dione
• CAS No.: 22177-46-4
• Molecular Formula: C9H8N2O2
• Molecular Weight: 176.175
• Hs Code.: 2933499090
• NSC Number: 110333
• UNII: 1IYV36MFF1
• DSSTox Substance ID: DTXSID80176712
• Wikidata: Q83047007
• ChEMBL ID: CHEMBL277286
• Mol file: 22177-46-4.mol

Synonyms:2-amino-1,2,3,4-tetrahydroisoquinoline-1,3-dione;2-aminoisoquinoline-1,3(2H,4H)-dione;ATHQD

Chemical Property of 2-Amino-1,2,3,4-tetrahydroisoquinoline-1,3-dione

Chemical Property:

• Vapor Pressure: 1.72E-05mmHg at 25°C
• Refractive Index: 1.635
• Boiling Point: 364.1 °C at 760 mmHg
• Flash Point: 174 °C
• PSA: 63.40000
• Density: 1.377 g/cm³
• LogP: 0.72340
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 176.058577502
• Heavy Atom Count: 13
• Complexity: 252

Purity/Quality:

99% ^*data from raw suppliers

2-Amino-1,2,3,4-tetrahydroisoquinoline-1,3-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=CC=CC=C2C(=O)N(C1=O)N

Technology Process of 2-Amino-1,2,3,4-tetrahydroisoquinoline-1,3-dione

There total 6 articles about 2-Amino-1,2,3,4-tetrahydroisoquinoline-1,3-dione 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: 71.0%

homophthalic anhydride (703-59-3) → 2-amino-1,2,3,4-tetrahydroisoquinoline-1,3-dione (22177-46-4)

Guidance literature:

With hydrazine hydrate; In ethanol; for 6h; Heating;

DOI:10.1055/s-2007-990893

Reference yield: 56.0%

3-bromo-1H-isochromen-1-one → 2-amino-1,2,3,4-tetrahydroisoquinoline-1,3-dione (22177-46-4)

Guidance literature:

With potassium carbonate; hydrazine; In 1,2-dichloro-ethane; at 20 ℃; for 1h;

DOI:10.2298/JSC201201025S

Reference yield:

Homophthalic acid (89-51-0) → 2-amino-1,2,3,4-tetrahydroisoquinoline-1,3-dione (22177-46-4)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / dichloromethane / Reflux

2: hydrazine hydrate / ethanol / Reflux

With thionyl chloride; hydrazine hydrate; In ethanol; dichloromethane;

DOI:10.1016/j.molstruc.2021.132007

upstream raw materials:

2,3-dihydro-5H-2,3-benzodiazepine-1,4-dione

acetic acid

homophthalic anhydride

hydrazine hydrate

Refernces

• 1、 Ozcan, Sevil,Dengiz, Cagatay,Deli?meroglu, Murat K.,Sahin, Ertan,Balci, Metin. "A novel one-pot, three-component reaction for the synthesis of isocoumarin-condensed pyrazoles". . p. 1495 - 1497. Retrieved 2011.
• 2、 Bori?, Ivan,Eri?, Slavica,Kiec-Kononowicz, Katarzyna,Latacz, Gniewomir,Lubelska, Annamaria,Nikodinovi?-Runi?, Jasmina,Savic, Vladimir M.,Simi?, Milena R.,Vojnovi?, Sandra. "Synthesis and biological profiling of novel isocoumarin derivatives and related compounds". . p. 639 - 649. Retrieved 2021/08/21.