1,3-Diphenylpropan-1,3-dion
DBM · 1,3-diphenylpropane-1,3-dione · 1,3-DIPHENYL-1,3-PROPANEDIONE · 1,3-Diphenylpropanedione · 1,3-diphenyl-3-propanedione · karenzudk2 · phenylphenacylketone · 2-Benzoylacetophenone
Identifikatoren & physikalische Daten
| CAS No. | 120-46-7 |
|---|---|
| Summenformel | C15H12O2 |
| Durchschnittliche Molmasse | 224,25 g/mol |
| Monoisotopische Masse | 224,08372962 g/mol |
| SMILES | O=C(CC(=O)c1ccccc1)c1ccccc1 |
| InChIKey | NZZIMKJIVMHWJC-UHFFFAOYSA-N |
| PubChem CID | 8433 |
| ChEMBL | CHEMBL371523 |
| ChEBI | CHEBI:75417 |
| EC No. | 204-398-9 |
| DTXSID | DTXSID3041247 |
| Lokaler Name | 1,3-Diphenylpropan-1,3-dion |
Chemische & physikalische Eigenschaften
| XLogP | 3,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 34,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 17 |
| Formalladung | 0 |
| Komplexität | 243 |
| Physical Description | Large CrystalsDry PowderSolid[Merck Index] Light yellow crystalline powder[Alfa Aesar MSDS] |
| Collision Cross Section | 165.9 Ų [M+Na]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID3041247]154.4 Ų [M-H]- [CCS Type: DTIonization: ESI- |
| Schmelzpunkt | 77-79 °C(lit.) |
| Siedepunkt | 219-221 °C18 mm Hg(lit.) |
| Dichte | 0.800 g/cm3 |
| Dampfdruck | 0.01Pa at 20℃ |
| Brechungsindex | 1.6600 (estimate) |
| Flammpunkt | 219-221°C/18mm |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | Chloroform (Slightly), Methanol (Slightly, Sonicated)It is Soluble in ether, chloroform, and aqueous sodium hydroxide. Insoluble in water. |
| pKa (Säurekonstante) | 8.95±0.10(Predicted) |
| Aggregatzustand | Crystals |
| Farbe | Light yellow to yellow |
| Merck | 14,3009 |
| BRN | 514910 |
| Henry-Konstante | 7.5×103 mol/(m3Pa) at 25℃, Zhang et al. (2010) |
| Stabilität | Stable. Incompatible with strong oxidizing agents. |
| InChI | 1S/C15H12O2/c16-14(12-7-3-1-4-8-12)11-15(17)13-9-5-2-6-10-13/h1-10H,11H2 |
| InChIKey | NZZIMKJIVMHWJC-UHFFFAOYSA-N |
| SMILES | O=C(CC(=O)c1ccccc1)c2ccccc2 |
| LogP (Verteilungskoeffizient) | 4.59 at 25℃ |
| CAS Datenbank | 120-46-7(CAS DataBase Reference) |
| NIST chemische Informationen | 1,3-Propanedione, 1,3-diphenyl-(120-46-7) |
| EPA chemische Informationen | 1,3-Propanedione, 1,3-diphenyl- (120-46-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 32.7% (84 of 257) of reports.WarningH317 (66.1%): May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 257 reports by companies from 6 notifications to the ECHA C&L Inventory.Reported as not meeting GHS hazard criteria per 84 of 257 reports by companies.There are 5 notifications provided by 173 of 257 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: 1,3-Propanedione, 1,3-diphenyl-1,3-Propanedione, 1,3-diphenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Propanedione, 1,3-diphenyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 13-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/113711,3-Propanedione, 1,3-diphenyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Causes changes in liver and uterine weights in 2-week constant oral studies of mice[RTECS] May cause irritation[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Sens. 1 (66.1%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29143900 |
| RTECS-Nr. | TZ1930000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | rat,LD,oral,> 500mg/kg (500mg/kg),National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 28, 1953. |
| Gefahrensymbole | Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 22-24/25 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Occurrence
Dibenzoylmethane(DBM) is a 1,3-diketone derivative of acetylacetone that has both methyl groups replaced with phenyl groups.Although smaller in size and lacking hydroxyl and methoxy groups，DBM resembles the turmeric spice curcumin (CUR),a diferuloylmethane. Both molecules are metal-chelating agents，contain a B-diketone flanked by two aryl groups,and exhibit anti-proliferative and anticarcinogenic activity. In addition to sharing structural similarity with DBM,CUR,which is also a naturally occurring compound is found in the plant Curcuma longa and has numerous medicinal uses.DBM and its many naturally occurring derivatives are minor constituentsof licorice. DBM has been isolated from licorice root extracts and otherspecies of Glycyrrhiza.
Verwenden
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.
Herstellung & Synthese
synthetische
dibenzoylmethane is prepared by condensation of ethyl benzoate with acetophenone.