1-(5-Bromo-2-methoxy-phenyl)adamantane CAS 104224-63-7
1-(5-Bromo-2-methoxy-phenyl)adamantane Basic information
| Product Name: | 1-(5-Bromo-2-methoxy-phenyl)adamantane |
| Synonyms: | 1-(5-BROMO-2-METHOXYPHENYL)TRYCYCLO[3,3,1,13,7]DECANE;1-(5-bromo-2-methoxyphenyl)-tricyclo[3,3,1,13,7]decane (intermediate of adapalene);1-(5-Bromo-2-methoxyphenyl)adamantane 97%;2-Adamantyl-4-bromo-1-methoxybenzene;2-Adamantyl-4-bromoanisole;2-(1-Adamantyl)-4-bromo-anisole (Adapalene);TRICYCLO[3.3.1.13,7]DECANE, 1-(5-BROMO-2-METHOXYPHENYL)-;1-(5-Bromo-2-methoxyphenyl)-tricyclo[3.3.1.13,7]decane |
| CAS: | 104224-63-7 |
| MF: | C17H21BrO |
| MW: | 321.25 |
| EINECS: | 689-408-3 |
| Product Categories: | API;Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Intermediates of Adapalene;Adamantane derivatives;APIs Intermediate;blocks;Bromides;ADAPALENE;(intermediate of adapalene) |
| Mol File: | 104224-63-7.mol |
1-(5-Bromo-2-methoxy-phenyl)adamantane Chemical Properties
| Melting point | 139-141°C |
| Boiling point | 402.5±38.0 °C(Predicted) |
| density | 1.346±0.06 g/cm3(Predicted) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | Chloroform (Slightly), Ethyl Acetate (Slightly) |
| form | Solid |
| color | White |
| InChI | InChI=1S/C17H21BrO/c1-19-16-3-2-14(18)7-15(16)17-8-11-4-12(9-17)6-13(5-11)10-17/h2-3,7,11-13H,4-6,8-10H2,1H3 |
| InChIKey | QQAMHHZQONQBFZ-UHFFFAOYSA-N |
| SMILES | C12(C3=CC(Br)=CC=C3OC)CC3CC(CC(C3)C1)C2 |
| CAS DataBase Reference | 104224-63-7(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Hazard Note | Irritant |
| HS Code | 2909309090 |
| Description | 1-(5-Bromo-2-methoxy-phenyl)adamantane is an organic synthesis reagent for the preparation of the adapalene intermediate 6-bromo-2-naphthalenecarboxylate. |
| Chemical Properties | 1-(5-Bromo-2-methoxy-phenyl)adamantane Appearance is white Solid or white to light yellow powder to crystalline, melting point 144℃. |
| Uses | Adapalene (A225000) impurity. |
| Synthesis | 104224-68-2 74-88-4 104224-63-7 To a stirred mixture of anhydrous N,N-dimethylformamide (5 ml) containing 2-(1-adamantyl)-4-bromophenol (0.5 g; 1.62 mmol) and anhydrous potassium carbonate (0.335 g; 2.42 mmol), iodomethane (1 ml) was added. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the mixture was diluted to 100 ml with distilled water and extracted with ethyl acetate (100 ml). The organic layers were combined, dried with anhydrous magnesium sulfate and filtered to remove the desiccant. The filtrate was filtered through silica gel column to remove impurities. Finally, the filtrate was concentrated to dryness under reduced pressure to give 1-(5-bromo-2-methoxyphenyl)adamantane (0.49 g, 94% yield) as a light yellow-green solid.1H-NMR (CDCl3) δ: 7.27-7.22 (m, 2H); 6.31 (d, 1H, J = 6.5 Hz); 3.78 (s, 3H); 2.04 (s, 10H). 1.74 (br, 5H). |
| References | [1] Patent: WO2010/43000, 2010, A1. Location in patent: Page/Page column 80 [2] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 14, p. 4863 - 4875 [3] European Journal of Medicinal Chemistry, 2014, vol. 79, p. 251 - 259 [4] Journal of Medicinal Chemistry, 1995, vol. 38, # 26, p. 4993 - 5006 [5] Patent: US4717720, 1988, A |
1-(5-Bromo-2-methoxy-phenyl)adamantane Preparation Products And Raw materials
| Raw materials | 2-(1-Adamantyl)-4-bromophenol-->1-Adamantanol-->Potassium carbonate-->4-Bromophenol-->N,N-Dimethylformamide-->Dimethyl sulfate-->Iodomethane-->4-Bromoanisole |
| Preparation Products | 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID |
