p-Hydroxyphenylessigsure
2-(4-hydroxyphenyl)acetic acid · P-HYDROXYPHENYLACETIC ACID · PHPA · 4-Hydroxybenzeneacetic acid · 4-carboxymethylphenol · Benzeneacetic acid, 4-hydroxy- · 4-Hydroxyphenylacetic · 4-hydrophenylacetic acid
Identifikatoren & physikalische Daten
| CAS No. | 156-38-7 |
|---|---|
| Summenformel | C8H8O3 |
| Durchschnittliche Molmasse | 152,15 g/mol |
| Monoisotopische Masse | 152,04734412 g/mol |
| SMILES | O=C(O)Cc1ccc(O)cc1 |
| InChIKey | XQXPVVBIMDBYFF-UHFFFAOYSA-N |
| PubChem CID | 127 |
| ChEMBL | CHEMBL1772 |
| ChEBI | CHEBI:18101 |
| EC No. | 205-851-3 |
| DTXSID | DTXSID5059745 |
| Lokaler Name | p-Hydroxyphenylessigsure |
Chemische & physikalische Eigenschaften
| XLogP | 0,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 57,5 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 136 |
| Stoffklassen | Other Classes -> Other Aromatic Compounds |
| SpringerMaterials Properties | Fusion temperature |
| LogP (Verteilungskoeffizient) | 0.751.26 |
| Löslichkeit | 60.7 mg/mL50g/lSoluble in dimethyl sulfoxide and methanol. Slightly soluble in water. |
| Schmelzpunkt | 148 - 150 °C148-151 °C(lit.) |
| Dampfdruck | 0.0000555 [mmHg]0.007Pa at 25℃ |
| Physical Description | Off-white crystalline powder[Alfa Aesar MSDS]Solid |
| Collision Cross Section | 126.65 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]135.22 Ų [M-H]- [CCS Type: DTMethod: stepped-field]128.6 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]128.9 Ų [M-H]- |
| Siedepunkt | 234.6°C (rough estimate) |
| Dichte | 1.2143 (rough estimate) |
| Brechungsindex | 1.4945 (estimate) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| pKa (Säurekonstante) | 4.50±0.10(Predicted) |
| Aggregatzustand | Crystalline Powder |
| Farbe | White to cream or light tan |
| pH | 2.0-2.4 (30g/l, H2O, 20℃) |
| BRN | 1448766 |
| InChI | 1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11) |
| InChIKey | XQXPVVBIMDBYFF-UHFFFAOYSA-N |
| SMILES | OC(=O)Cc1ccc(O)cc1 |
| LogP (Verteilungskoeffizient) | 0.75 at 25℃ |
| CAS Datenbank | 156-38-7(CAS DataBase Reference) |
| NIST chemische Informationen | Benzeneacetic acid, 4-hydroxy-(156-38-7) |
| EPA chemische Informationen | Benzeneacetic acid, 4-hydroxy- (156-38-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (97%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 233 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Benzeneacetic acid, 4-hydroxy-Status: Cease Manufacture Update: 01-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/22446(4-Hydroxyphenyl)-acetic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Gefahrenübersicht | Intraperitoneal LD50 (mouse) = 3,500 mg/kg[RTECS] An irritant[Alfa Aesar MSDS] See Phenylacetic acid. |
| Hazard Classes and Categories | Skin Irrit. 2 (97%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29182990 |
| RTECS-Nr. | AI2680000 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-36-24/25 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Verwenden
A compound present in olive oil. An important fine chemical intermediate with broad prospects for application development.
Herstellung & Synthese
synthetische
4-Hydroxyphenylacetic acid is synthesized by diazotization and hydrolysis of 4-aminophenylacetic acid. 4-aminophenylacetic acid and alkali solution are prepared into sodium salt, and then sulfuric acid is added. Cool to 0°C, control the temperature at 0-5°C, and add sodium nitrate solution dropwise, and the reaction is completed for 0.5h. The obtained diazonium was added dropwise to dilute sulfuric acid at 90-95°C for about 1 hour, and the reaction was continued for 1 hour. The reaction solution was decolorized and filtered, cooled and extracted with ethyl acetate, and the extract was recovered with ethyl acetate to obtain 4-Hydroxyphenylacetic acid. The yield is about 85%.