1,3-Propanedione, 1-(2-hydroxyphenyl)-3-(3-nitrophenyl)-

Base Information

• Chemical Name: 1,3-Propanedione, 1-(2-hydroxyphenyl)-3-(3-nitrophenyl)-
• CAS No.: 109899-85-6
• Molecular Formula: C15H11NO5
• Molecular Weight: 285.256
• DSSTox Substance ID: DTXSID40402347
• Wikidata: Q82205743
• Mol file: 109899-85-6.mol

Synonyms:1,3-Propanedione, 1-(2-hydroxyphenyl)-3-(3-nitrophenyl)-;109899-85-6;Oprea1_765184;DTXSID40402347

Chemical Property of 1,3-Propanedione, 1-(2-hydroxyphenyl)-3-(3-nitrophenyl)-

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 285.06372245
• Heavy Atom Count: 21
• Complexity: 417

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(=O)CC(=O)C2=CC(=CC=C2)[N+](=O)[O-])O

Technology Process of 1,3-Propanedione, 1-(2-hydroxyphenyl)-3-(3-nitrophenyl)-

There total 7 articles about 1,3-Propanedione, 1-(2-hydroxyphenyl)-3-(3-nitrophenyl)- 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:

2'-(3-nitrobenzoyloxy)acetophenone (109899-88-9) → 1-(2-hydroxyphenyl)-3-(3-nitrophenyl)propane-1,3-dione (109899-85-6)

Guidance literature:

potassium tert-butylate; In dimethyl sulfoxide; at 30 ℃; Rate constant; buffer cont. 0.02M 2,4,6-trimethylphenol; substituent effects; acidity function correlations;

Reference yield:

o-hydroxyacetophenone (118-93-4,104809-67-8) → 1-(2-hydroxyphenyl)-3-(3-nitrophenyl)propane-1,3-dione (109899-85-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / POCl₂ / pyridine / 3 h / 60 - 70 °C

2: NaH / tetrahydrofuran / 3 h / Heating

With sodium hydride; In tetrahydrofuran; pyridine; 2: Baker-Venkataraman rearrangement;

DOI:10.1007/s00706-006-0550-9

Reference yield:

o-hydroxyacetophenone (118-93-4,104809-67-8) + m-nitrobenzoic acid chloride (121-90-4) → 1-(2-hydroxyphenyl)-3-(3-nitrophenyl)propane-1,3-dione (109899-85-6)

Guidance literature:

With lithium hexamethyldisilazane; Multistep reaction; 1.) THF, 078 deg C, 2 h, 2.) THF, a) -78 deg C, 1 h, b) RT, 20 h;

DOI:10.1021/jm00046a020

upstream raw materials:

2'-(3-nitrobenzoyloxy)acetophenone

o-hydroxyacetophenone

m-nitrobenzoic acid chloride

3-nitrobenzoic acid

Downstream raw materials:

6,3'-Dinitroflavone

3',6-diaminoflavone

C₂₁H₁₃N₅O₇

2-(3-aminophenyl)-4H-chromen-4-one