Acrylophenone, 2',4'-dihydroxy-3-(m-hydroxy-p-methoxyphenyl)-

Base Information

• Chemical Name: Acrylophenone, 2',4'-dihydroxy-3-(m-hydroxy-p-methoxyphenyl)-
• CAS No.: 13323-67-6
• Molecular Formula: C16H14 O5
• Molecular Weight: 286.284
• Nikkaji Number: J437.478I
• Wikidata: Q76305628
• Metabolomics Workbench ID: 26589
• ChEMBL ID: CHEMBL4791427
• Mol file: 13323-67-6.mol

Synonyms:4-O-methylbutein

Chemical Property of Acrylophenone, 2',4'-dihydroxy-3-(m-hydroxy-p-methoxyphenyl)-

Chemical Property:

• Vapor Pressure: 5.97E-13mmHg at 25°C
• Melting Point: 198.5-200.5℃
• Boiling Point: 555.6°C at 760 mmHg
• PKA: 7.33±0.35(Predicted)
• Flash Point: 210.6°C
• PSA: 86.99000
• Density: 1.369g/cm³
• LogP: 2.70810
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 286.08412354
• Heavy Atom Count: 21
• Complexity: 381

Purity/Quality:

≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C=CC(=O)C2=C(C=C(C=C2)O)O)O
• Isomeric SMILES: COC1=C(C=C(C=C1)/C=C/C(=O)C2=C(C=C(C=C2)O)O)O

Technology Process of Acrylophenone, 2',4'-dihydroxy-3-(m-hydroxy-p-methoxyphenyl)-

There total 6 articles about Acrylophenone, 2',4'-dihydroxy-3-(m-hydroxy-p-methoxyphenyl)- 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: 83.0%

2’,3,4’-triisopropoxy-4-methoxychalcone (1417453-13-4) → 2’,3,4’-trihydroxy-4-methoxychalcone (13323-67-6)

Guidance literature:

With boron trichloride; In hexane; dichloromethane; at -78 - 0 ℃; for 3.5h; Inert atmosphere;

DOI:10.1039/c2ob27163j

Reference yield:

isovanillin (621-59-0) + 2',4'-dihydroxy-4-acetophenone (89-84-9) → 2’,3,4’-trihydroxy-4-methoxychalcone (13323-67-6) + 7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one (76426-28-3)

Guidance literature:

With potassium hydroxide; In isopropyl alcohol; at 80 ℃; Reflux;

DOI:10.3390/molecules25061382

Reference yield:

2,4-diisopropoxyacetophenone (728911-59-9) → 2’,3,4’-trihydroxy-4-methoxychalcone (13323-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: barium hydroxide octahydrate / methanol / 50 °C / Inert atmosphere

2: boron trichloride / dichloromethane; hexane / 3.5 h / -78 - 0 °C / Inert atmosphere

With barium hydroxide octahydrate; boron trichloride; In methanol; hexane; dichloromethane; 1: |Claisen-Schmidt Condensation;

DOI:10.1039/c2ob27163j

upstream raw materials:

2’,3,4’-triisopropoxy-4-methoxychalcone

2,4-diisopropoxyacetophenone

O-isopropylisovanillin

2',4'-dihydroxy-4-acetophenone

Downstream raw materials:

7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-benzo(b)pyran-4-one

C₁₉H₁₈Br₂O₅

C₁₉H₁₈O₅

Refernces

• 1、 Amslinger, Sabine,Al-Rifai, Nafisah,Winter, Katrin,W?rmann, Kilian,Scholz, Rebekka,Baumeister, Paul,Wild, Martin. "Reactivity assessment of chalcones by a kinetic thiol assay". supporting information. p. 549 - 554. Retrieved 2013/03/13.