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Chemical Structure| 36953-37-4 Chemical Structure| 36953-37-4
Chemical Structure| 36953-37-4

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4-Bromo-2-hydroxypyridine is a biochemical reagent that can serve as a biological material or organic compound for life science-related research.

Synonyms: 4-Bromo-2-pyridone

4.5 *For Research Use Only !

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Product Details of 4-Bromo-2-hydroxypyridine

CAS No. :36953-37-4
Formula : C5H4BrNO
M.W : 174.00
SMILES Code : O=C1C=C(Br)C=CN1
Synonyms :
4-Bromo-2-pyridone
MDL No. :MFCD11226860
InChI Key :SSLMGOKTIUIZLY-UHFFFAOYSA-N
Pubchem ID :817115

Safety of 4-Bromo-2-hydroxypyridine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 4-Bromo-2-hydroxypyridine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 36953-37-4 ]

[ 36953-37-4 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 36953-37-4 ]
  • [ 100-39-0 ]
  • [ 960298-00-4 ]
YieldReaction ConditionsOperation in experiment
With silver carbonate; In benzene; at 20 - 50℃; for 40h;Protection from light; A mixture of 4-Bromo-1H-pyridin-2-one (0.613 g), silver carbonate (0.63 g) and benzyl bromide (0.50 mL) in benzene (10 mL) was heated at 50C for 24 hours, protected from light. Reaction mixture stirred ambient temperature for 16 hours. Reaction mixture was filtered through a pad of CELITE, which was washed ethyl acetate. The filtrate was concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give 2-Benzyloxy-4-bromo-pyridine (0.6043 g): LCMS-ESI+: calc'd for C12H11BrNO: 265.12 (M+H+); Found: 263.8, 265.8 (M+H+).
  • 2
  • [ 36953-37-4 ]
  • [ 100-39-0 ]
  • [ 960298-00-4 ]
  • 1-benzyl-4-bromopyridin-2(1H)-one [ No CAS ]
  • 3
  • [ 36953-37-4 ]
  • [ 75-03-6 ]
  • [ 832735-58-7 ]
YieldReaction ConditionsOperation in experiment
84% Under argon atmosphere, a solution of 4-bromo-1,2-dihydropyridin-2-one (1.00 g, 5.75 mmol) in THF (20 mL) was treated with sodium hydride (60% dispersion in mineral oil, 230 mg, 5.75 mmol) at 0C and then stirred 30 minutes at room temperature. Iodoethane (1.39 mL, 17.25 mmol) was added to the mixture and the reaction was stirred for 16 hours at room temperature and then heated at 50 C for 24 hours. The middle was diluted with water and ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (DCM/EtOAc 100/0 to 85/15) to give compound (150a) (981 mg, 4.86 mmol, 84%).
  • 4
  • [ 960298-00-4 ]
  • [ 36953-37-4 ]
YieldReaction ConditionsOperation in experiment
82% With hydrogenchloride; In methanol;Reflux; To a solution of <strong>[960298-00-4]2-benzyloxy-4-bromopyridine</strong> 6 (201 mg, 0.8 mmol) in MeOH(4.5 mL) was added conc. HCl (2.3 mL). The mixture was heated at reflux overnight.Then the reaction mixture was cooled to room temperature and concentrated underreduced pressure. The residue was poured into cold water and carefully quenchedwith aq. sat. Na2CO3. The aqueous layer was extracted with ethyl acetate (3x). Thecombined organic layers were washed with brine, dried (Na2SO4), filtered andconcentrated under reduced pressure. The crude was purified by flash chromatography on silica gel (EtOAc/MeOH: 98/2) to give 1c (109 mg, 82%) as acolorless solid. Data for 1c are reported above.
  • 5
  • [ 36953-37-4 ]
  • ethyl halide [ No CAS ]
  • [ 832735-58-7 ]
YieldReaction ConditionsOperation in experiment
81% General procedure: To an ice-cold solution of 2-hydroxy-4-bromopyridine (5.75 mmol) in THF was added NaH (5.75 mmol) portion-wise. The reaction mixture was stirred in an ice-bath for 15 min followed by addition of halide or iodine (17.24 mmol). The resulting reaction mixturewas stirred at room temperature for 16 h. After the completion of the reaction, 20 mL of H2O was added and the reaction mixture was extracted with EtOAc 3 times. The combined organic layer was collected and rinsed with brine. The mixture was evaporated to obtain the crude product and purified by silica gel for 3a-3d.
 

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