| Identification | Back Directory | [Name]
5-BROMO-8-METHYL-QUINOLINE | [CAS]
74316-55-5 | [Synonyms]
5-BROMO-8-METHYL-QUIN
5-BROMO-8-METHYL-QUINOLINE
Quinoline, 5-bromo-8-methyl- | [Molecular Formula]
C10H8BrN | [MDL Number]
MFCD04966995 | [MOL File]
74316-55-5.mol | [Molecular Weight]
222.08 |
| Chemical Properties | Back Directory | [Melting point ]
37-38 °C | [Boiling point ]
315.7±22.0 °C(Predicted) | [density ]
1.488±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
3.95±0.29(Predicted) | [Appearance]
White to off-white Solid |
| Hazard Information | Back Directory | [Synthesis]
Step 1: Synthesis of 5-bromo-8-methylquinoline
8-Methylquinoline (0.3 M) was dissolved in concentrated H2SO4, Ag2SO4 (1.5 equiv) and bromine (1.0 equiv) were added. The reaction mixture was stirred at room temperature for 5 hours and then poured into ice water to quench the reaction. The precipitate was removed by filtration and the filtrate was alkalized with saturated aqueous Na2CO3 to pH > 7. The aqueous phase was extracted with EtOAc (3×), the organic layers were combined and dried over anhydrous Na2SO4. The organic phase was concentrated under reduced pressure to afford the target product 5-bromo-8-methylquinoline in 71% yield as a white solid. Mass spectrum (ESI+) m/z: 222, 224 [M+H]+. | [References]
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1980, vol. 16, # 3, p. 275 - 277
[2] Khimiya Geterotsiklicheskikh Soedinenii, 1980, vol. 16, # 3, p. 366 - 368
[3] Tetrahedron, 2005, vol. 61, # 41, p. 9696 - 9704
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 8, p. 2836 - 2848
[5] Patent: WO2007/28789, 2007, A1. Location in patent: Page/Page column 34 |
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