| Identification | More | [Name]
1-(5-Bromo-2-methoxy-phenyl)adamantane | [CAS]
104224-63-7 | [Synonyms]
1-(5-bromo-2-methoxy-phenyl)adamantane
1-(5-Bromo-2-methoxyphenyl)-tricyclo[3.3.1.13,7]decane
2-(1-ADAMANTANE)-4-BROMOANISOLE
2-(1-ADAMANTYL)-4-BROMOANISOLE
TRICYCLO[3.3.1.13,7]DECANE, 1-(5-BROMO-2-METHOXYPHENYL)-
2-(Adamantan-1-yl)-4-bromoanisole, 2-(Adamantan-1-yl)-4-bromo-1-methoxybenzene
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)
Anisole, 2-(1-adamantyl)-4-bromo-
1-(5-bromo-2-methoxyphenyl)- | [EINECS(EC#)]
689-408-3 | [Molecular Formula]
C17H21BrO | [MDL Number]
MFCD03855308 | [Molecular Weight]
321.25 | [MOL File]
104224-63-7.mol |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [Description]
1-(5-Bromo-2-methoxy-phenyl)adamantane(104224-63-7) is an organic synthesis reagent for the preparation of the adapalene intermediate 6-bromo-2-naphthalenecarboxylate.
| [Chemical Properties]
White Solid | [Uses]
Adapalene (A225000) impurity. | [Synthesis]
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 |
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