8-Aminoisoquinoline CAS 23687-27-6
8-Aminoisoquinoline Basic information
| Product Name: | 8-Aminoisoquinoline |
| Synonyms: | 8-AMINOISOQUINOLINE;ISOQUINOLIN-8-AMINE;ISOQUINOLIN-8-YLAMINE;8-Aminoisoquinoline95%;8-Aminoisoquinoline 98%;8-amine-isoquinoline;8-Isoquinolinamine;8-Aminoisoquinoline ,98% |
| CAS: | 23687-27-6 |
| MF: | C9H8N2 |
| MW: | 144.17 |
| EINECS: | 691-616-4 |
| Product Categories: | Building Blocks;Isoquinoline;Amines;blocks;Quinolines;Quinoline&Isoquinoline;Heterocyclic Series |
| Mol File: | 23687-27-6.mol |
8-Aminoisoquinoline Chemical Properties
| Melting point | 155-157 |
| Boiling point | 335.7±17.0 °C(Predicted) |
| density | 1.210±0.06 g/cm3(Predicted) |
| storage temp. | Keep in dark place,Inert atmosphere,2-8°C |
| form | Crystalline Powder |
| pka | 6.20±0.23(Predicted) |
| color | Brown |
| InChI | InChI=1S/C9H8N2/c10-9-3-1-2-7-4-5-11-6-8(7)9/h1-6H,10H2 |
| InChIKey | GUSYANXQYUJOBH-UHFFFAOYSA-N |
| SMILES | C1C2=C(C=CC=C2N)C=CN=1 |
| CAS DataBase Reference | 23687-27-6(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 41 |
| Safety Statements | 26-39 |
| WGK Germany | WGK 3 |
| Hazard Note | Harmful/Irritant/Keep Cold |
| HS Code | 29334900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Eye Dam. 1 |
| Chemical Properties | Brown solid |
| Uses | 8-Aminoisoquinoline and its derivatives are used as intermediates for antimalarial drugs in the pharmaceutical field. For example, their structure is similar to the antimalarial drug primaquine. |
| Synthesis | 63927-23-1 23687-27-6 General procedure for the synthesis of 8-aminoisoquinolines from 5-bromo-8-nitroisoquinolines: 5-bromo-8-nitroisoquinolines (1.00 g, 3.95 mmol) were dissolved in methanol (70 mL), and hydrogenation was carried out by adding palladium/activated charcoal (10% Pd, 200 mg) as a catalyst for 18 hr at room temperature and atmospheric pressure. Upon completion of the reaction, the reaction mixture was filtered through Celite to remove the catalyst. The filtrate was concentrated and purified by column chromatography (eluent: ethyl acetate/heptane) to afford the target compound 8-aminoisoquinoline (100 mg, 18% yield) as a greenish-brown solid.1H NMR (DMSO-d6, 400 MHz) δ 9.43 (s, 1H), 8.32 (d, 1H), 7.54 (d, 1H), 7.40 (dd, 1H) , 6.99 (d, 1H), 6.72 (d, 1H), 6.22 (s, 2H). |
| References | [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 4, p. 803 - 806 [2] Journal of Medicinal Chemistry, 2005, vol. 48, # 3, p. 744 - 752 [3] Patent: WO2009/130481, 2009, A1. Location in patent: Page/Page column 143 [4] Journal of Medicinal Chemistry, 2005, vol. 48, # 15, p. 4972 - 4982 [5] Patent: WO2006/32851, 2006, A1. Location in patent: Page/Page column 49 |
8-Aminoisoquinoline Preparation Products And Raw materials
| Raw materials | Ethyl acetate-->Methanol-->Diethyl ether-->Sulfuric acid-->PETROLEUM ETHER-->Sodium carbonate-->Sodium sulfate-->Magnesium sulfate-->Triethylamine-->Ammonium hydroxide-->Sodium chloride-->Hexane-->Hydrogen-->N-Bromosuccinimide-->Ammonium acetate-->Potassium nitrate-->Palladium hydroxide-->Heptane-->Isoquinoline |
