Identification | Back Directory | [Name]
2-BROMO-5-METHOXYPYRIDINE | [CAS]
105170-27-2 | [Synonyms]
2-BROMO-5-METHOXYPYRIDINE Pyridine,2-bromo-5-methoxy- 2-BROMO-5-METHOXYPYRIDINE ISO 9001:2015 REACH | [Molecular Formula]
C6H6BrNO | [MDL Number]
MFCD07781221 | [MOL File]
105170-27-2.mol | [Molecular Weight]
188.02 |
Chemical Properties | Back Directory | [Melting point ]
22 °C | [Boiling point ]
113 °C(Press: 59 Torr) | [density ]
1.530±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
soluble in Methanol | [form ]
powder to lump | [pka]
-2.22±0.10(Predicted) | [color ]
White to Almost white | [InChI]
InChI=1S/C6H6BrNO/c1-9-5-2-3-6(7)8-4-5/h2-4H,1H3 | [InChIKey]
WULVUFYZVYHTFX-UHFFFAOYSA-N | [SMILES]
C1(Br)=NC=C(OC)C=C1 | [CAS DataBase Reference]
105170-27-2 |
Hazard Information | Back Directory | [Chemical Properties]
Pale yellow liquid | [Uses]
2-Bromo-5-methoxypyridine is a reagent used in preparation of tetrahydroisoquinoline amides as bronchodilators. | [Synthesis]
General procedure for the synthesis of 2-bromo-5-methoxypyridine from 2-amino-5-methoxypyridine:
(a) 2-Amino-5-methoxypyridine (14.8 g, prepared according to the method described by JG Lombardino, J. Med. Chem., 1981, 24, 39) was dissolved in 60% hydrobromic acid (150 ml) and cooled to -10°C. Bromine (47.47 g) was added slowly and dropwise with stirring. A solution of sodium nitrite (20.53 g) in water (40 ml) was added dropwise to the resulting yellow suspension, keeping the reaction temperature below -5°C. The mixture was stirred to room temperature and cooled to 0°C after 0.5 h. A solution of sodium hydroxide (120 g) in water (100 ml) was added slowly. The mixture was fully extracted with ether, the ether extracts were combined and dried with anhydrous sodium sulfate, followed by evaporation of the solvent. The residue was purified by column chromatography on silica gel (150 g), using dichloromethane as eluent to give a yellow oil (14.1 g, 63% yield). This product was combined with a smaller batch (3.4 g) and purified by distillation under reduced pressure to give finally 2-bromo-5-methoxypyridine (16.4 g) with a boiling point of 76°C-78°C/0.6 torr. | [References]
[1] Pharmazie, 2000, vol. 55, # 12, p. 907 - 912 [2] Patent: US4766121, 1988, A [3] Patent: EP188351, 1991, B1 [4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 3085 - 3096 |
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