6-Bromo-2-methylquinoline CAS 877-42-9
6-Bromo-2-methylquinoline Basic information
| Product Name: | 6-Bromo-2-methylquinoline |
| Synonyms: | 6-BROMOQUINAIDINE;6-BROMO-2-METHYLQUINOLINE;6-BROMOQUINALDINE;6-Bromoquinaldine, 6-Bromo-2-methyl-1-azanaphthalene;6-BroMo-2-Methylquinoline, 97+%;Quinoline, 6-bromo-2-methyl-;6-Bromoquildine, 98%;6-Bromo-2-methylquinoline > |
| CAS: | 877-42-9 |
| MF: | C10H8BrN |
| MW: | 222.08 |
| EINECS: | |
| Product Categories: | Quinoline&Isoquinoline;Alkylquinolines;Haloquinolines;Quinolines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;QuinolinesHeterocyclic Building Blocks |
| Mol File: | 877-42-9.mol |
6-Bromo-2-methylquinoline Chemical Properties
| Melting point | 101-105 °C (lit.) |
| Boiling point | 299.7±20.0 °C(Predicted) |
| density | 1.488±0.06 g/cm3(Predicted) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | soluble in Methanol |
| pka | 5.02±0.43(Predicted) |
| form | solid |
| color | Grey |
| InChI | 1S/C10H8BrN/c1-7-2-3-8-6-9(11)4-5-10(8)12-7/h2-6H,1H3 |
| InChIKey | SQRYQSKJZVQJAY-UHFFFAOYSA-N |
| SMILES | Cc1ccc2cc(Br)ccc2n1 |
| CAS DataBase Reference | 877-42-9(CAS DataBase Reference) |
| NIST Chemistry Reference | 6-Bromoquinaldine(877-42-9) |
Safety Information
| Hazard Codes | Xn,Xi |
| Risk Statements | 22-37/38-42-36/37/38-20/21/22 |
| Safety Statements | 26-39-36/37/39-24/25-22 |
| WGK Germany | 3 |
| Hazard Note | Irritant |
| HS Code | 29339900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Eye Dam. 1 Resp. Sens. 1 Skin Irrit. 2 Skin Sens. 1 STOT SE 3 |
| Chemical Properties | white to light yellow crystal powder |
| Synthesis | 106-40-1 123-73-9 877-42-9 GENERAL METHOD: 4-Bromoaniline (1.50 mmol) and trans-2-butenal (1.00 mmol) were dissolved in 1.5 mL of ether (Et2O) in a reaction flask fitted with a magnetic stir bar, followed by the addition of silver(I)-exchanged montmorillonite K10 (0.50 g). After stirring for 5 min, the solvent was removed under vacuum to obtain a dry powder. The reaction mixture was heated at 120 °C for 3 hours. After the reaction mixture was cooled to room temperature, it was filtered through a short silica gel plug and the solid residue was washed well with dichloromethane (CH2Cl2). After removal of the solvent under vacuum, the crude product was purified by silica gel column chromatography, eluting using a solvent mixture of hexane/ethyl acetate (EtOAc) to give the final 6-bromo-2-methylquinoline (3a-3k). Note: For recycling/reuse studies, the crude product is separated by gravity filtration and the clay material is washed several times with dichloromethane (CH2Cl2), air-dried and weighed. The process is repeated for successive recycling/reuse reactions. |
| References | [1] Advanced Functional Materials, 2012, vol. 22, # 2, p. 345 - 352 [2] Heterocycles, 2016, vol. 92, # 12, p. 2213 - 2224 [3] Tetrahedron Letters, 2011, vol. 52, # 22, p. 2840 - 2843 [4] Chemical Communications, 2012, vol. 48, # 35, p. 4196 - 4198 [5] Dalton Transactions, 2012, vol. 41, # 20, p. 6189 - 6194 |
6-Bromo-2-methylquinoline Preparation Products And Raw materials
| Raw materials | Bis[(pinacolato)boryl]Methane-->2-Amino-5-bromobenzaldehyde-->Ethyl vinyl ether-->6-Bromoquinoline-->Formaldehyde-->6-bromo-1-oxido-quinoline-->Crotonaldehyde (trans predominantly)-->Ethanol-->4-Bromoaniline |
| Preparation Products | METHYL 6-BROMOQUINOLINE-2-CARBOXYLATE-->6-Bromoquinoline-2-carboxylic acid-->6-Fluoroquinaldine-->6-ethynyl-2-methylquinoline-->6-Bromo-quinoline-2-carboxylic acid amide |
