4'-Hydroxyacetophenon
4-HYDROXYACETOPHENONE · P-HYDROXYACETOPHENONE · Piceol · POB · P-HYDROXYBENZOPHENONE · para-Hydroxyacetophenone · ACETYLPHENOL · 4-ACETYLPHENOL
Identifikatoren & physikalische Daten
| CAS No. | 99-93-4 |
|---|---|
| Summenformel | C8H8O2 |
| Durchschnittliche Molmasse | 136,15 g/mol |
| Monoisotopische Masse | 136,0524295 g/mol |
| SMILES | CC(=O)c1ccc(O)cc1 |
| InChIKey | TXFPEBPIARQUIG-UHFFFAOYSA-N |
| PubChem CID | 7469 |
| ChEMBL | CHEMBL201083 |
| ChEBI | CHEBI:28032 |
| EC No. | 202-802-8 |
| DTXSID | DTXSID0029133 |
| Lokaler Name | 4'-Hydroxyacetophenon |
Chemische & physikalische Eigenschaften
| XLogP | 1,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 123 |
| Stoffklassen | Other Classes -> Aromatic Ketones |
| Kosmetika | Cosmetic ingredients (Hydroxyacetophenone) -> CIR (Cosmetic Ingredient Review) |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Duftstoffe | Fragrance Ingredient (4-Hydroxyacetophenone) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | 1.45 |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Aromastoffe | EU Flavoring substances |
| Löslichkeit | Practically insoluble or insoluble in waterSoluble (in ethanol)methanol: 0.1 g/mL, clear10 g/L (22 ºC) |
| Dampfdruck | 0.00748 [mmHg]0.002Pa at 20℃ |
| Physical Description | Other SolidLiquidWhite or off-white powder[Alfa Aesar MSDS]White to off-white crystals, chips or chunksSlight berry to sweet balsam aroma |
| Collision Cross Section | 125.5 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID0029133] |
| Schmelzpunkt | 132-135 °C(lit.) |
| Siedepunkt | 147-148 °C3 mm Hg(lit.) |
| Dichte | 1.109 |
| Brechungsindex | 1.5577 (estimate) |
| FEMA | 4330 | 4-HYDROXYACETOPHENONE |
| Flammpunkt | 166 °C |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | 8.05(at 25℃) |
| Farbe | Almost white to beige |
| Wichte | 1.109 |
| Geruch | at 10.00 % in dipropylene glycol. mild sweet hawthorn balsam mimosa |
| Geruchsart | floral |
| JECFA Number | 2040 |
| BRN | 774355 |
| Kosmetik-Inhaltsstoffe Funktionen | ANTIOXIDANT |
| InChI | 1S/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H3 |
| InChIKey | TXFPEBPIARQUIG-UHFFFAOYSA-N |
| SMILES | CC(=O)c1ccc(O)cc1 |
| LogP (Verteilungskoeffizient) | 1.35 at 25℃ |
| CAS Datenbank | 99-93-4(CAS DataBase Reference) |
| NIST chemische Informationen | Acetophenone, 4'-hydroxy-(99-93-4) |
| EPA chemische Informationen | 4-Hydroxyacetophenone (99-93-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 3.9% (11 of 279) of reports.WarningH302 (45.2%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 279 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Ethanone, 1-(4-hydroxyphenyl)-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Ethanone, 1-(4-hydroxyphenyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanone, 1-(4-hydroxyphenyl)- 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: 12-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/11354Ethanone, 1-(4-hydroxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Safe when used as a flavoring agent in food[EFSA] A skin and strong eye irritantToxic by ingestion[Alfa Aesar MSDS] See 2'-Hydroxyacetophenone, 3'-Hydroxyacetophenone, and Acetophenone. |
| EPA Safer Chemical | Chemical: 4-Hydroxyacetophenone |
| Hazard Classes and Categories | Acute Tox. 4 (45.2%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29145000 |
| RTECS-Nr. | PC4959775 |
| R-Sätze (R) | 36/37/38-22 |
| Gefahrensymbole | Xn,Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-36/37-37/39-24/25-22-36 |
| Lagerklasse | 13 - Non Combustible Solids |
| Gefahrenklasse | Aquatic Chronic 3Eye Irrit. 2 |
Anwendungen & Verwendung
Occurrence
Reported found in cloudberry, coffee, cranberry, mango, sherry, and wort.
Verwenden
4-Hydroxyacetophenone has been used as ketone component in the preparation of 1-aryl-3-phenethylamino-1-propanone hydrochlorides, potential cytotoxic agents, via Mannich reactions.
Herstellung & Synthese
synthetische
Preparation by Fries rearrangement of phenyl acetate with Lewis acidsaluminium chloridein nitrobenzene at 20–25° or at 50–60°in chlorobenzene between 45° and 65°, sealed tube and subjected to high power microwave irradiation for 2 min only (36%) in nitroethane at 60° (44%)in carbon disulfide at 45° (40%)in petroleum ether at 50° (20%) but between 130° and 175° (40–60%)aluminium chloride–sodium chloride mixture at 240–250° (10%) boron trifluoride at 90° (56%) scandium tris(trifluoromethanesulfonate), in nitromethane, at 50° (39%)titanium tetrachloride at 90–100° (34%)ferric chloride at 65° (25%)zinc chloride at 125° (8%) hydrofluoric acid, between 20° and 100° (94%) polyphosphoric acid, between 20° and 100° (69%) (50–53%)(44%)Nafion-XR 500, sulfonic acid type at 100°ZSM-5, in sulfolane, at 180° (28%)H-ZSM-5 at 400° or at 210° (6%) H-Nu-2 at 170° (15%)HY (Si/Al = 3) or fluorided alumina (Al2O3-F; 3 % wt. F), at 400°.