4-Phenylbutenon
4-PHENYL-3-BUTEN-2-ONE · (E)-4-Phenylbut-3-en-2-one · BENZYLIDENEACETONE · benzylidene · 4-Phenylbut-3-en-2-one · 3-Buten-2-one, 4-phenyl- · Benzalaceton · (3E)-4-phenylbut-3-en-2-one
Identifikatoren & physikalische Daten
| CAS No. | 122-57-6 |
|---|---|
| Summenformel | C10H10O |
| Durchschnittliche Molmasse | 146,19 g/mol |
| Monoisotopische Masse | 146,07316494 g/mol |
| SMILES | CC(=O)C=Cc1ccccc1 |
| InChIKey | BWHOZHOGCMHOBV-UHFFFAOYSA-N |
| PubChem CID | 15909 |
| ChEMBL | CHEMBL3187978 |
| EC No. | 204-555-1 |
| DTXSID | DTXSID4025662 |
| Lokaler Name | 4-Phenylbutenon |
Chemische & physikalische Eigenschaften
| XLogP | 2,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 17,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 152 |
| SpringerMaterials Properties | Boiling point |
| Duftstoffe | Fragrance substance (Benzylidene acetone) -> IFRA amendment 40 |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Aromastoffe | EU Flavoring substances |
| Löslichkeit | insoluble in watersoluble in organic solvents, oilsvery soluble (in ethanol)Soluble in alcohol, chloroform, diethyl ether.1.398g/L(25 ºC) |
| Siedepunkt | 260 °C260-262 °C(lit.) |
| Physical Description | colourless to slightly yellow crystalline solid with a sweet, pungent, creamy, floral odour |
| Schmelzpunkt | 39-42 °C(lit.) |
| Dichte | 1.038 |
| Dampfdruck | 0.01 mm Hg ( 25 °C) |
| Brechungsindex | 1.5836 |
| FEMA | 2881 | 4-PHENYL-3-BUTEN-2-ONE |
| Flammpunkt | 150 °F |
| Lagerbedingungen | Store at <= 20°C. |
| Aggregatzustand | Low Melting Solid |
| Farbe | Pale yellow to yellow |
| Geruch | Sweet, but rather pungent odor with a creamy-floral note. |
| Geruchsart | spicy |
| Biologische Quelle | synthetic |
| Merck | 14,1137 |
| JECFA Number | 820 |
| BRN | 742046 |
| Stabilität | Light Sensitive |
| InChI | 1S/C10H10O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8H,1H3/b8-7+ |
| InChIKey | BWHOZHOGCMHOBV-BQYQJAHWSA-N |
| SMILES | [H]\C(=C(\[H])c1ccccc1)C(C)=O |
| LogP (Verteilungskoeffizient) | 2.04 |
| CAS Datenbank | 122-57-6(CAS DataBase Reference) |
| NIST chemische Informationen | 3-Buten-2-one, 4-phenyl-(122-57-6) |
| EPA chemische Informationen | Benzylideneacetone (122-57-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 2.6% (50 of 1901) of reports.WarningH315 (84.2%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P272, P280, P302+P352, P321, P332+P317, P333+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1901 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 3-Buten-2-one, 4-phenyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 17-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/5367Benzylideneacetone: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (84.2%) |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| F | 8 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29143900 |
| RTECS-Nr. | EN0330050 |
| R-Sätze (R) | 36/37/38-43-42/43 |
| Toxizität | LD50 orally in Rabbit: 2031 mg/kg |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 7-26-36/37/39-45-37/39-24-36/37-22 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Skin Irrit. 2Skin Sens. 1 |
Anwendungen & Verwendung
Beschreibung
Benzylidenaceton bildet farblose nach Cumarin riechende Tafeln. Es schmilzt bei 42 ℃ und siedet bei Normaldruck zwischen 260 und 262 ℃. Benzylidenaceton ist löslich in Alkohol, Benzol, Chloroform und Ether, während es in Wasser kaum löslich ist. In der organischen Chemie ist es ein wichtiger Synthese-Baustein für Michael-Additionen, Kondensation-, Cycloadditions- und Grignard-Reaktionen.
Occurrence
Occasionally Benzalacetone is used in perfumery for Sweet Pea (used to be a “must” in this type of fragrance), in Appleblossom, etc., often in combination with Neroli and Hyacinth bases. Also used in flavors, particularly in Chocolate, Cocoa, Cherry, Fruit, Nut, Vanilla, etc. - but usually at very low concentration. Concentration in finished product will rarely exceed 0.2 to 0.5 ppm.
Verwenden
brightener in acid zinc electroplating,also used as an organic synthesis intermediate in flavor and fragrance, pharmaceutical industries
Herstellung & Synthese
synthetische
By condensing benzaldehyde and acetone in the presence of an alkaline condensing agent.