4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-on
4-AAP · AMPYRONE · AMINOANTIPYRINE · 4-AMINOPHENAZONE · 4-AMINOANTIPYRIN · 4-Amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one · 4-AMINOANTIPYRENE · 4-AMINO-2,3-DIMETHYL-1-PHENYL-3-PYRAZOLIN-5-ONE
Identifikatoren & physikalische Daten
| CAS No. | 83-07-8 |
|---|---|
| Summenformel | C11H13N3O |
| Durchschnittliche Molmasse | 203,24 g/mol |
| Monoisotopische Masse | 203,10586204 g/mol |
| SMILES | Cc1c(N)c(=O)n(-c2ccccc2)n1C |
| InChIKey | RLFWWDJHLFCNIJ-UHFFFAOYSA-N |
| PubChem CID | 2151 |
| ChEMBL | CHEMBL1165011 |
| ChEBI | CHEBI:59026 |
| EC No. | 201-452-3 |
| DTXSID | DTXSID8048860 |
| Lokaler Name | 4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-on |
Chemische & physikalische Eigenschaften
| XLogP | 0,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 49,6 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 305 |
| Arzneimittel | Pharmaceuticals -> Metabolite of Metamizole |
| Animal Drugs | Pharmaceuticals -> Animal Drugs -> Approved in Taiwan |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Collision Cross Section | 151.49 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]142.6 Ų [M+H]+ [CCS Type: TW142.48 Ų [M+H]+ |
| Schmelzpunkt | 105-110 °C(lit.) |
| Siedepunkt | 340 C |
| Dichte | 0.8 |
| Brechungsindex | 1.4930 (estimate) |
| Lagerbedingungen | Keep in dark place,Inert atmosphere,Room temperature |
| Löslichkeit | H2O: 0.1 g/mL, clearca. 500 g/L (20 ºC) |
| pKa (Säurekonstante) | pK1: 4.94(+1) (25°C) |
| Aggregatzustand | Powder or Crystals |
| Farbe | Yellow to yellow-brown |
| pH | 7.1 (100g/l, H2O, 20℃)(slurry) |
| Geruch | Odorless |
| Merck | 14,591 |
| BRN | 181635 |
| Stabilität | Stable. May be light sensitive. |
| InChI | 1S/C11H13N3O/c1-8-10(12)11(15)14(13(8)2)9-6-4-3-5-7-9/h3-7H,12H2,1-2H3 |
| InChIKey | RLFWWDJHLFCNIJ-UHFFFAOYSA-N |
| SMILES | CN1N(c2ccccc2)C(=O)C(N)=C1C |
| LogP (Verteilungskoeffizient) | -0.257 (est) |
| CAS Datenbank | 83-07-8(CAS DataBase Reference) |
| NIST chemische Informationen | Aminoantipyrene(83-07-8) |
| EPA chemische Informationen | 4-Aminoantipyrene (83-07-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1% (1 of 105) of reports.WarningH302 (99%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, 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 105 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | 4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 3H-Pyrazol-3-one, 4-amino-1,2-dihydro-1,5-dimethyl-2-phenyl-: Environment tier I assessment |
| Hazard Classes and Categories | Acute Tox. 4 (99%) |
| F | 8-9-23 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29331190 |
| RTECS-Nr. | CD2480000 |
| R-Sätze (R) | 22-36/37/38-20/21/22 |
| Toxizität | LD50 orally in Rabbit: 1700 mg/kg |
| Gefahrensymbole | Xn |
| hazard_note | Harmful |
| Sicherheitshinweise (S) | 26-36-36/37/39 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 Oral |
Anwendungen & Verwendung
Verwenden
4-Aminoantipyrine is a metabolite of aminopyrine, having both analgesic and anti-inflammatory properties. It readily forms metal complexes due to its amino nitrogen, a strong coordination site.4-aminoantipyrine forms Schiff bases when treated with aldehydes/ketones, which are used in chemosensing applications.Coupling Reagent for Trinder's reagent in colorimetric hydrogen peroxide detectionassays.Forms highly stable dyes by coupling with Trinder's reagent in presence of Peroxidase and H2O2. Therefore suitable for use in test strip and solution diagnostics.
Herstellung & Synthese
synthetische
synthesis of 4-aminoantipyrine: Antipyrine is nitrosated by sodium nitrite, reduced by ammonium bisulfite and ammonium sulfite, hydrolyzed by sulfuric acid, and finally neutralized with liquid ammonia to obtain 4-aminoantipyrine.