1-chloro-1,2-dihydroisoquinoline
1-Chloroisoquinoline
CAS: 19493-44-8
Molecular Formula: C9H6ClN
1-chloro-1,2-dihydroisoquinoline - Names and Identifiers
| Name | 1-Chloroisoquinoline |
| Synonyms | 1-Chloroisoquinone chloroisoquinoline 1-CHLOROISOQUINOLINE 1-Chloroisoquinoline Isoquinoline, 1-chloro- 1-chloro-1,2-dihydroisoquinoline |
| CAS | 19493-44-8 |
| EINECS | 628-561-2 |
| InChI | InChI=1/C9H6ClN/c10-9-8-4-2-1-3-7(8)5-6-11-9/h1-6H |
| InChIKey | MSQCQINLJMEVNJ-UHFFFAOYSA-N |
1-chloro-1,2-dihydroisoquinoline - Physico-chemical Properties
| Molecular Formula | C9H6ClN |
| Molar Mass | 163.6 |
| Density | 1.2108 (rough estimate) |
| Melting Point | 31-36 °C (lit.) |
| Boling Point | 274-275 °C/768 mmHg (lit.) |
| Flash Point | >230°F |
| Water Solubility | Insoluble in water. |
| Vapor Presure | 0.00902mmHg at 25°C |
| Appearance | Low Melting Solid, Crystals and/or Chunks |
| Color | White to yellow |
| BRN | 2996 |
| pKa | 2.03±0.30(Predicted) |
| Storage Condition | Inert atmosphere,2-8°C |
| Refractive Index | 1.6342 (estimate) |
1-chloro-1,2-dihydroisoquinoline - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| HS Code | 29334900 |
1-chloro-1,2-dihydroisoquinoline - Reference Information
| Application | 1-chloroisoquinoline can be used as a pharmaceutical synthesis intermediate, such as the preparation of compound 1-phenylisoquinoline. 1-chloroisoquinoline can be prepared from N-vinylbenzamide as a reaction starting material. |
| preparation | 1) an oven-dried 25ml Schlenk tube equipped with a magnetic stir bar was charged sequentially with N-vinylbenzamide (0.2mmol),[Cp * RhCl2]2(3mol%,4.8mg),Ag2O(0.2mmol,49.6mg),t-BuOLi(0.5mmol,40mg) and toluene (1ml), the reaction mixture was stirred under a nitrogen balloon at 50°C for 5 hours, the reaction mixture was filtered, the solvent was evaporated in vacuo, the crude product was purified by flash column chromatography on silica gel using petroleum ether and ethyl acetate (PE:EA = 5:1) as eluents, N-(1-oxo-2-vinyl-1, 2,3, 4-tetrahydroisoquinolin-3-yl) benzamide was obtained. 2) N-(1-oxo-2-ethenyl-1, 2,3, 4-tetrahydroisoquinolin-3-yl) benzamide (0.2mmol),POCl3(2eq), toluene (1ml), the reaction mixture was stirred at 80 °c for 12 h, the reaction mixture was filtered, the solvent was evaporated in vacuo and the crude product was purified by flash column chromatography on silica gel using petroleum ether and ethyl acetate (PE:EA = 5:1) as eluent to obtain 1-chloroisoquinoline. |
| Use | for manganese-catalyzed coupling reactions of aryl and alkyl magnesium halides, it is also used in palladium-catalyzed coupling reactions of isoaryl boronic acids and esters. |
Last Update：2024-04-09 20:52:54
