Losoxantrone

Base Information

• Chemical Name: Losoxantrone
• CAS No.: 88303-60-0
• Molecular Formula: C₂₂H₂₇N₅O₄
• Molecular Weight: 425.487
• UNII: 47KPH00809
• DSSTox Substance ID: DTXSID60236949
• Nikkaji Number: J265.016I
• Wikipedia: Losoxantrone
• Wikidata: Q21098832
• NCI Thesaurus Code: C1521
• Metabolomics Workbench ID: 144656
• ChEMBL ID: CHEMBL83520
• Mol file: 88303-60-0.mol

Synonyms:7-hydroxy-2(2-((2-hydroxyethyl) amino) ethyl)5-(2-((2-hydroxyethyl)amino)ethyl)amino anthra(1,9-cd)pyrazole-6(2H)-one;anthrapyrazolone;Biantrazole;CI 941;CI-941;DuP 941;DUP-941;losoxantrone;NSC 357885;PD 113785

Chemical Property of Losoxantrone

Chemical Property:

• Vapor Pressure: 1.27E-24mmHg at 25°C
• Boiling Point: 765.2°C at 760 mmHg
• Flash Point: 416.6°C
• PSA: 131.67000
• Density: 1.46g/cm³
• LogP: 1.27680
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 425.20630436
• Heavy Atom Count: 31
• Complexity: 596

Purity/Quality:

99% ^*data from raw suppliers

LOSOXANTRONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)O)C(=O)C3=C(C=CC4=C3C2=NN4CCNCCO)NCCNCCO

Technology Process of Losoxantrone

There total 11 articles about Losoxantrone 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: 80.0%

5-chloro-2-<2-<(2-hydroxyethyl)amino>ethyl>-7-hydroxyanthra<1,9-cd>pyrazol-6(2H)-one hydrochloride (123839-75-8) + 2-(2-Aminoethylamino)ethanol (111-41-1) → 7-hydroxy-2-{2-[(2-hydroxyethyl)amino]ethyl}-5-({2-[(2-hydroxyethyl)amino]ethyl}amino)anthra(1,9-cd)pyrazol-6(2H)-one (88303-60-0)

Guidance literature:

With pyridine; at 82 ℃; for 21h;

DOI:10.1002/jhet.5570260117

Reference yield: 55.0%

→ 7-hydroxy-2-{2-[(2-hydroxyethyl)amino]ethyl}-5-({2-[(2-hydroxyethyl)amino]ethyl}amino)anthra(1,9-cd)pyrazol-6(2H)-one (88303-60-0)

Guidance literature:

Reference yield:

1,4-dichloro-5-hydroxy-9,10-anthracenedione (6770-15-6) → 7-hydroxy-2-{2-[(2-hydroxyethyl)amino]ethyl}-5-({2-[(2-hydroxyethyl)amino]ethyl}amino)anthra(1,9-cd)pyrazol-6(2H)-one (88303-60-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / K₂CO₃ / acetone / Heating

2: dimethylsulfoxide

3: pyridine / Heating

4: H₂, glacial AcOH / 20percent Pd(OH)2/C

With pyridine; hydrogen; potassium carbonate; acetic acid; palladium dihydroxide; In dimethyl sulfoxide; acetone;

DOI:10.1021/jm00369a002

upstream raw materials:

2-<2-<(2-hydroxyethyl)amino>ethyl>-5-<<2-<(2-hydroxyethyl)amino>ethyl>amino>-7-(phenylmethoxy)anthra<1,9-cd>pyrazol-6(2H)-one

5-<<2-<(2-hydroxyethyl)amino>ethyl>amino>-2-<2-<(2-hydroxyethyl)(phenylmethyl)amino>ethyl>-7-(phenylmethoxy)anthra<1,9-cd>pyrazol-6(2H)-one

5-chloro-2-<2-<(2-hydroxyethyl)amino>ethyl>-7-hydroxyanthra<1,9-cd>pyrazol-6(2H)-one hydrochloride

2-(2-Aminoethylamino)ethanol

Downstream raw materials:

losoxantrone