8-Bromoquinoline CAS 16567-18-3
8-Bromoquinoline Basic information
| Product Name: | 8-Bromoquinoline |
| Synonyms: | 8-BROMOQUIOLINE;RARECHEM AK ML 0146;8-bromooquinoline;8-Bromoquinoline ,97%;8-Bromoquinoline,96%;Quinoline, 8-Bromo-;8-BroMoquinoline, 96% 500MG;8-BroMoquinolline |
| CAS: | 16567-18-3 |
| MF: | C9H6BrN |
| MW: | 208.05 |
| EINECS: | 630-629-1 |
| Product Categories: | Quinolines, Isoquinolines & Quinoxalines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Quinolines;QuinolinesHeterocyclic Building Blocks;Halogenated;Organohalides;Quinoline;blocks;Bromides;Heterocycles;Quinoline series;Quinolines, Quinazolines and derivatives;Halides;Quinolines, Isoquinolines & Quinoxalines;Quinoline&Isoquinoline;Quinoline Derivertives |
| Mol File: | 16567-18-3.mol |
8-Bromoquinoline Chemical Properties
| Melting point | 58-59 °C |
| Boiling point | 112-113 °C/0.5 mmHg (lit.) |
| density | 1.594 g/mL at 25 °C (lit.) |
| refractive index | n |
| Fp | >230 °F |
| storage temp. | Inert atmosphere,2-8°C |
| pka | 2.33±0.17(Predicted) |
| form | Liquid After Melting |
| color | Clear yellow to yellow-brown |
| Specific Gravity | 1.594 |
| Sensitive | Light Sensitive |
| InChI | InChI=1S/C9H6BrN/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H |
| InChIKey | PIWNKSHCLTZKSZ-UHFFFAOYSA-N |
| SMILES | N1C2C(=CC=CC=2Br)C=CC=1 |
| CAS DataBase Reference | 16567-18-3(CAS DataBase Reference) |
| NIST Chemistry Reference | Quinoline, 8-bromo-(16567-18-3) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36-37/39 |
| WGK Germany | 3 |
| Hazard Note | Irritant |
| HS Code | 29334900 |
| Storage Class | 10 - Combustible liquids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Chemical Properties | white to light yellow crystal powder |
| Uses | 8-Bromoquinoline may be used in the following studies:
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| General Description | 8-Bromoquinoline is a quinolone derivative. It is widely employed for the synthesis of dyes, food colors, pharmaceutical reagents, pH indicators and in various industrial processes. Its molecule bears a pyridyl group. It undergoes direct heteroarylation reaction with various heteroaromatic compounds in the presence of a palladium catalyst to afford polyheteroaromatic derivatives. |
| Synthesis | 3054-95-3 615-36-1 16567-18-3 GENERAL PROCEDURE: A 1N HCl solution (82.5 mL) was added to a round-bottomed flask containing o-bromoaniline (~1 mmol). Acrolein diethyl acetal (2.5 mmol) was then added. The reaction mixture was refluxed at 111 °C for 24 hours. After completion of the reaction, it was cooled to room temperature and neutralized to pH 7-8 with solid Na2CO3. The product was extracted with dichloromethane (3 x 100 mL), the organic layers were combined and dried over anhydrous Na2SO4. The solvent was removed by evaporation under reduced pressure to give the crude product. The crude product was purified by column chromatography using a solvent mixture of hexane and ethyl acetate (or 15% ethyl acetate/cyclohexane and methanol) as eluent to give the target product 8-bromoquinoline. |
| References | [1] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6436 - 6439 |
8-Bromoquinoline Preparation Products And Raw materials
| Raw materials | Sulfuric acid-->Glycerol-->Sodium iodide-->2-Bromoaniline-->Sodium iodide dihydrate-->Acrolein diethyl acetal-->Hydrochloric acid-->Water |
| Preparation Products | 8-Quinolineboronic acid-->METHYLQUINOLINE-8-CARBOXYLATE |
