4-Aminophenylessigsure
2-(4-AMINOPHENYL)ACETIC ACID · H-4-APH-OH · 4-Aminophenylacetic · P-AMINOPHENYLACETIC ACID · NSC 7929 · H-APH(4)-OH · 4-AMino acid · p-Amino-alph
Identifikatoren & physikalische Daten
| CAS No. | 1197-55-3 |
|---|---|
| Summenformel | C8H9NO2 |
| Durchschnittliche Molmasse | 151,16 g/mol |
| Monoisotopische Masse | 151,06332853 g/mol |
| SMILES | Nc1ccc(CC(=O)O)cc1 |
| InChIKey | CSEWAUGPAQPMDC-UHFFFAOYSA-N |
| PubChem CID | 14533 |
| ChEMBL | CHEMBL3278327 |
| EC No. | 214-828-7 |
| DTXSID | DTXSID1061609 |
| Lokaler Name | 4-Aminophenylessigsure |
Chemische & physikalische Eigenschaften
| XLogP | 0,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 63,3 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 139 |
| Stoffklassen | Nitrogen Compounds -> Other Aromatics (Nitrogen) |
| Physical Description | Solid[Merck Index] Tan powder[Alfa Aesar MSDS] |
| Schmelzpunkt | 201 °C (dec.) (lit.) |
| Siedepunkt | 273.17°C (rough estimate) |
| Dichte | 1.2023 (rough estimate) |
| Brechungsindex | 1.5635 (rough estimate) |
| Flammpunkt | 201°C |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | pK1: 3.60pK2: 5.26 (20°C) |
| Aggregatzustand | Powder |
| Farbe | Light yellow to beige |
| Löslichkeit | Very soluble in water. |
| Decomposition | 201 ºC |
| Merck | 14,463 |
| BRN | 2208094 |
| InChI | 1S/C8H9NO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5,9H2,(H,10,11) |
| InChIKey | CSEWAUGPAQPMDC-UHFFFAOYSA-N |
| SMILES | Nc1ccc(CC(O)=O)cc1 |
| LogP (Verteilungskoeffizient) | 0.220 (est) |
| CAS Datenbank | 1197-55-3(CAS DataBase Reference) |
| NIST chemische Informationen | Benzeneacetic acid, 4-amino-(1197-55-3) |
| EPA chemische Informationen | Benzeneacetic acid, 4-amino- (1197-55-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): 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 9 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Benzeneacetic acid, 4-amino-Benzeneacetic acid, 4-amino-: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | A skin and strong eye irritantMay induce methemoglobinemia[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Unerwünschte Wirkungen | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect |
| F | 13 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29224995 |
| RTECS-Nr. | AF3550000 |
| R-Sätze (R) | 36/37/38-20/21/22 |
| Toxizität | mouse,LD50,intraperitoneal,3500mg/kg (3500mg/kg),Farmaco, Edizione Scientifica. Vol. 13, Pg. 286, 1958. |
| Gefahrensymbole | Xi,Xn |
| Sicherheitshinweise (S) | 22-24/25-36-26 |
| Gefahrenklasse | IRRITANT |
| Lagerklasse | 13 - Non Combustible Solids |
Anwendungen & Verwendung
Verwenden
4-Aminophenylacetic acid is used as a non-translocated competitive inhibitor of the epithelial peptide transporter PepT1. It can be detected using HPLC, NMR techniques.
Herstellung & Synthese
synthetische
p-aminophenylacetic acid is obtained by the reduction of 4-nitrophenylacetic acid. In a reactor, water, 4-nitrophenylacetic acid, and acetic acid are added. The mixture is stirred and heated to 90-95℃. Iron powder is added in portions and refluxed for 2 hours. The mixture is cooled to 40-50℃ and neutralized with sodium carbonate to pH=9, then filtered. The filtrate is further neutralized with acetic acid until pH=4, resulting in the precipitation of 4-aminophenylacetic acid. The yield is 95%.