Irenolone

Base Information

• Chemical Name: Irenolone
• CAS No.: 149184-19-0
• Molecular Formula: C19H12 O3
• Molecular Weight: 288.3
• Nikkaji Number: J552.816J
• Wikidata: Q104402330
• Metabolomics Workbench ID: 49139
• ChEMBL ID: CHEMBL1164175
• Mol file: 149184-19-0.mol

Synonyms:Irenolone;149184-19-0;2-hydroxy-4-(4-hydroxyphenyl)phenalen-1-one;CHEMBL1164175;CHEBI:189809;AKOS004902211;2-hydroxy-4-(4-hydroxyphenyl)-1H-phenalen-1-one

Chemical Property of Irenolone

Chemical Property:

• Boiling Point: 573.7±50.0 °C(Predicted)
• PKA: 7.69±0.20(Predicted)
• PSA: 57.53000
• Density: 1.433±0.06 g/cm3(Predicted)
• LogP: 4.30760
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 288.078644241
• Heavy Atom Count: 22
• Complexity: 475

Purity/Quality:

98.5% ^*data from raw suppliers

Irenolone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C3C(=C1)C(=O)C(=CC3=C(C=C2)C4=CC=C(C=C4)O)O

Technology Process of Irenolone

There total 7 articles about Irenolone 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: 100.0%

2-hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one (159853-36-8) → irenolone (149184-19-0)

Guidance literature:

With boron tribromide; In dichloromethane; for 0.25h;

DOI:10.1016/S0040-4020(01)85707-0

Reference yield:

Perinaphthenon (548-39-0) → irenolone (149184-19-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) 2,3-dichloro-5,6-dicyano-p-benzoquinone / 1.) ether, reflux, 3 h, 2.) CH₂Cl₂, reflux, 3 h

2: 1.) DIBAH, 2.) Jones reagent / 1.) toluene, -78 deg C, 4 h, 2.) acetone, room temp., 15 min

3: 70percent t-butyl-hydroperoxide, 40percent benzyltrimethylammonium hydroxide / benzene / Ambient temperature

4: p-toluenesulfonic acid / CH₂Cl₂ / 2 h

5: 100 percent / boron tribromide / CH₂Cl₂ / 0.25 h

With tert.-butylhydroperoxide; jones reagent; boron tribromide; N-benzyl-trimethylammonium hydroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)85707-0

Reference yield:

9-(4-methoxyphenyl)-1H-phenalen-1-one (65874-43-3) → irenolone (149184-19-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) DIBAH, 2.) Jones reagent / 1.) toluene, -78 deg C, 4 h, 2.) acetone, room temp., 15 min

2: 70percent t-butyl-hydroperoxide, 40percent benzyltrimethylammonium hydroxide / benzene / Ambient temperature

3: p-toluenesulfonic acid / CH₂Cl₂ / 2 h

4: 100 percent / boron tribromide / CH₂Cl₂ / 0.25 h

With tert.-butylhydroperoxide; jones reagent; boron tribromide; N-benzyl-trimethylammonium hydroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; In dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)85707-0

upstream raw materials:

2-hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one

Perinaphthenon

9-(4-methoxyphenyl)-1H-phenalen-1-one

4-methoxyphenyl magnesium bromide

Refernces