Dibenzoylmethane

Base Information

• Chemical Name: Dibenzoylmethane
• CAS No.: 120-46-7
• Deprecated CAS: 61346-73-4,2090414-61-0
• Molecular Formula: C15H12O2
• Molecular Weight: 224.259
• Hs Code.: DERIVATION
• European Community (EC) Number: 204-398-9
• NSC Number: 6266
• UNII: ANS7ME8OKC
• DSSTox Substance ID: DTXSID3041247
• Nikkaji Number: J10.072B
• Wikipedia: Dibenzoylmethane
• Wikidata: Q5272260
• Metabolomics Workbench ID: 133043
• ChEMBL ID: CHEMBL371523
• Mol file: 120-46-7.mol

Synonyms:dibenzoylmethane

Chemical Property of Dibenzoylmethane

Chemical Property:

• Appearance/Colour: yellowish-white powder
• Vapor Pressure: 1.63E-06mmHg at 25°C
• Melting Point: 77-79 °C(lit.)
• Refractive Index: 1.623
• Boiling Point: 357.4 °C at 760 mmHg
• PKA: 8.95±0.10(Predicted)
• Flash Point: 146.9 °C
• PSA: 34.14000
• Density: 1.138 g/cm³
• LogP: 3.14230
• Storage Temp.: Store at RT.
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• Water Solubility.: It is Soluble in ether, chloroform, and aqueous sodium hydroxide. Insoluble in water.
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 224.083729621
• Heavy Atom Count: 17
• Complexity: 243

Purity/Quality:

99% ^*data from raw suppliers

Dibenzoylmethane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones
• Canonical SMILES: C1=CC=C(C=C1)C(=O)CC(=O)C2=CC=CC=C2
• Uses: Dibenzoylmethane is a new kind of PVC heat stabilizer, it has better transparency, nontoxic and odorless. In case of combined use with Calcium/Zinc, Barium/Zin and other heat stabilizer, it can greatly improve the initial color, transparency, long term stability of PVC, and also can improve the precipitation and “zinc burning” problem during the process. It has very good synergy with zinc soaps, and can protect the PVC color. This material can absorb UV at 290nm, which has the effect as light stabilizer and act as long term stabilizer for PVC products. Dibenzoylmethane is a compound known to inhibit tumorigenesis in mice.

Technology Process of Dibenzoylmethane

There total 219 articles about Dibenzoylmethane 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: 91.0%

3,3-dibromo-1,3-diphenyl-1,3-propanedione (16619-55-9) + phenol (108-95-2,27073-41-2) → 4-bromo-phenol (106-41-2) + 1,3-diphenylpropanedione (120-46-7,61346-73-4)

Guidance literature:

at 100 ℃; for 48h;

DOI:10.1016/j.tet.2009.10.049

Reference yield: 66.0%

octanoic acid ethyl ester (106-32-1) + acetophenone (98-86-2) → 10-methyl-heptadec-9-en-8-one (145494-20-8) + dypnone (495-45-4) + 1,3-diphenyl-2-(1-phenylethylidene)propane-1,3-dione (39568-00-8) + 1,3-diphenylpropanedione (120-46-7,61346-73-4) + Heptadec-9-yn-8-one + octanoyl benzoyl methane (68892-13-7)

Guidance literature:

With sodium amide; 1.) ether, 2.) ether, heating, 3 h;

DOI:10.1002/prac.19923340512

Reference yield: 60.0%

N-isopropylbenzamide (5440-69-7) + 1-(1-phenylvinyl)pyrrolidine (3433-56-5) → (E)-N-isopropyl-1,3-diphenylprop-2-en-1-amine + 1,3-diphenylpropanedione (120-46-7,61346-73-4) + 1,3-diphenyl-propen-3-one (614-47-1)

Guidance literature:

N-isopropylbenzamide; With 2-fluoropyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at 0 ℃; for 0.333333h; Inert atmosphere; Schlenk technique;

1-(1-phenylvinyl)pyrrolidine; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere; Schlenk technique;

With sodium tetrahydroborate; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; for 6h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.7b03943

upstream raw materials:

hydrogen cyanide

bis-(1-benzoyl-2-oxo-2-phenyl-ethyl)-selenide

benzoic acid ethyl ester

sodium ethanolate

Downstream raw materials:

(E)-3-methoxy-1,3-diphenylprop-2-en-1-one

(2Z)-3-methoxy-1,3-diphenylprop-2-en-1-one

(Z)-3-ethoxy-1,3-diphenylprop-2-en-1-one

(E)-3-morpholin-4-yl-1,3-diphenylpropenone

Refernces

Predominance of 2-arylhydrazones of 1,3-diphenyl-propane-1,2,3-trione over its proton-transfer products

10.1002/poc.435

The research focuses on the tautomeric preferences of 2-phenylhydrazones of 1,3-diphenyl-1,2,3-trione in chloroform solution, as detected by 15N NMR chemical shifts. The study aims to understand whether the substituent in the phenylhydrazone moiety influences the tautomeric preference and the transmission of the substituent effect within the molecules. Experiments involved the synthesis of compounds through the coupling of benzenediazonium ion to 1,3-diphenyl-1,3-propanedione, followed by purification via recrystallization from ethanol. The synthesized compounds were then analyzed using 1H, 13C, and 15N NMR spectroscopy, with chemical shifts referenced to tetramethylsilane (TMS) and nitromethane. Additionally, ab initio calculations at the HF/B3LYP level of theory with GIAO-HF/DFT method were conducted to calculate the chemical shifts of carbon atoms, and X-ray crystallography was used to detect the tautomer in the crystal state. The study found that the ketohydrazone tautomer is significantly favored over its proton-transfer products, and this tautomer was also detected in the crystalline state, indicating that the additional carbonyl group or substituent does not affect the tautomeric and configurational preferences.