8-Chinolylamin
QUINOLIN-8-AMINE · 8-QUINOLINAMINE · Quinolin-8-ylaMine · nc066 · wr6920 · AS-232 · 8-Amino · AKOS 91147
Identifikatoren & physikalische Daten
| CAS No. | 578-66-5 |
|---|---|
| Summenformel | C9H8N2 |
| Durchschnittliche Molmasse | 144,17 g/mol |
| Monoisotopische Masse | 144,06874826 g/mol |
| SMILES | Nc1cccc2cccnc12 |
| InChIKey | WREVVZMUNPAPOV-UHFFFAOYSA-N |
| PubChem CID | 11359 |
| ChEMBL | CHEMBL99932 |
| EC No. | 209-427-9 |
| DTXSID | DTXSID4060369 |
| Lokaler Name | 8-Chinolylamin |
Chemische & physikalische Eigenschaften
| XLogP | 1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 38,9 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 136 |
| Dampfdruck | 0.00055 [mmHg] |
| Physical Description | Yellow solidified mass or fragments[Aldrich MSDS] |
| Schmelzpunkt | 60-65 °C (lit.) |
| Siedepunkt | 174 °C/26 mmHg (lit.) |
| Dichte | 1.1148 (estimate) |
| Brechungsindex | 1.7080 (estimate) |
| Flammpunkt | 174°C/26mm |
| Lagerbedingungen | Keep in dark place,Inert atmosphere,Room temperature |
| pKa (Säurekonstante) | pK1: 3.99(+1) (20°C,μ=0.01) |
| Aggregatzustand | Crystalline Powder |
| Farbe | Green to beige-brown |
| Löslichkeit | slightly soluble |
| BRN | 114474 |
| InChI | 1S/C9H8N2/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H,10H2 |
| InChIKey | WREVVZMUNPAPOV-UHFFFAOYSA-N |
| SMILES | Nc1cccc2cccnc12 |
| CAS Datenbank | 578-66-5(CAS DataBase Reference) |
| NIST chemische Informationen | 8-Quinolinamine(578-66-5) |
| EPA chemische Informationen | 8-Quinolinamine (578-66-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (19.2%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H341 (11.5%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, 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 52 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: 8-Quinolinamine8-Aminoquinoline: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | A skin and strong eye irritant[Aldrich MSDS] See 5-Aminoquinoline. |
| Hazard Classes and Categories | Skin Irrit. 2 (100%)Eye Irrit. 2A (100%)STOT SE 3 (19.2%)Muta. 2 (11.5%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN2811 |
| Zollcode | 29334990 |
| RTECS-Nr. | VA9627000 |
| R-Sätze (R) | 68-36/37/38-20/21/22-36/38 |
| Toxizität |
Anwendungen & Verwendung
Verwenden
8-Aminoquinoline is used as pesticide and pharmaceutical intermediate. It has been used in the preparation of base-stabilized terminal borylene complex of osmium. It is also used in the spectrophotometric determination of bivalent palladium.
Herstellung & Synthese
synthetische
Synthesis of 8-aminoquinoline: Under an ice bath, sulfuric acid (2.0 mL) was added onto quinoline (5 mmol, 1.0 equiv) then 65% nitric acid (3.0 equiv) were added dropwise and stirred for 4h at rt. The mixture was poured into the ice water and neutralized with NaOH; and then extracted with dichloromethane. After dried over Na2SO4 and evaporated in vacuo, used next step without purification.Mixture of nitroquinolines and 5% Pd/C was solved in ethanol and suspension was saturated with hydrogen gas under atmospheric pressure at 40°C until the starting material was consumed. 2 h later, the mixture was filtered and evaporated. The crude product was purified by silica gel column chromatography, eluting with EtOAc in hexanes to yield the desired 8-aminoquinoline is isolated as a brown solid in a yield of 32%.Obtained as a brown solid (231 mg, 32%); 1H NMR (500 MHz, CDCl3) δ 8.71 – 8.60 (m, 1H), 7.93 (d, J = 8.2 Hz, 1H), 7.29 – 7.16 (m, 2H), 7.02 (d, J = 8.1 Hz, 1H), 6.80 (d, J = 7.4 Hz, 1H), 4.89 (s, 2H).