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

3-oxo-1,3-diphenylprop-1-en-1yl benzoate

3-(2-methyl-indol-3-yl)-1,3-diphenyl-propenone

Refernces

• 1、 Potgieter, J. H.. "Kinetics of the substitution of β-Diketones in β-diketonato(1,5-cyclooctadiene)rhodium(I) complexes by benzoyl-1,1,1-trifluoroacetone". . p. 369 - 376. Retrieved 1989.
• 2、 Blanton, James R.,Salley, Robert E.. "Preparation and Utilization of a Macromolecular Analogue of N-tert-Butyl-N-ethylamine as a Reusable Amide Base". . p. 723 - 726. Retrieved 1989.
• 3、 Chen, Rener,Wu, Huayue,Zhang, Yongmin. "A novel synthesis of 1,3-diketones by reaction of an α-bromoketone with acyl chlorides promoted by gallium triiodide". . p. 666 - 667. Retrieved 1999.
• 4、 Tajbakhsh,Hosseinzadeh,Sadatshahabi. "Synthesis and application of 2,6-dicarboxy pyridinium fluorochromate as a new solid-phase oxidant". . p. 1547 - 1554. Retrieved 2005.
• 5、 Anselme. "-". . p. 3716. Retrieved 1967.
• 6、 Wang, Ai-E,Yu, Cun-Cun,Chen, Ting-Ting,Liu, Yong-Peng,Huang, Pei-Qiang. "Enamines as Surrogates of Alkene Carbanions for the Reductive Alkenylation of Secondary Amides: An Approach to Allylamines". . p. 999 - 1002. Retrieved 2018.
• 7、 Degl'Innocenti, Alessandro,Pike, Stephen,Walton, David R. M.,Seconi, Giancarlo,Ricci, Alfredo,Fiorenza, Mariella. "Acylsilanes and C-Stannylimines as Anion Equivalents". . p. 1201 - 1202. Retrieved 1980.
• 8、 Seki et al.. "-". . p. 528. Retrieved 1975.
• 9、 Noyce,de Bruin. "-". . p. 372. Retrieved 1968.
• 10、 Rao,Filler. "-". . p. 1447. Retrieved 1971.