| Identification | Back Directory | [Name]
5-Bromo-2-hydroxy-3-(trifluoromethyl)pyridine | [CAS]
76041-79-7 | [Synonyms]
5-BROMO-3-TRIFLUOROMETHYL-2-PYRIDONE
2-hydroxy-5-broMo-3-trifluoropyridine
5-Bromo-3-(trifluoromethyl)pyridin-2-ol
5-BroMo-3-trifluoroMethyl-1H-pyridin-2-one
5-broMo-3-(trifluoroMethyl)-2(1H)-pyridinone
5-Bromo-2-hydroxy-3-(trifluoromethyl)pyridine
5-Bromo-3-(trifluoromethyl)pyridin-2-ol, 5-Bromo-2-hydroxy-alpha,alpha,alpha-trifluoro-3-picoline | [Molecular Formula]
C6H3BrF3NO | [MDL Number]
MFCD12546486 | [MOL File]
76041-79-7.mol | [Molecular Weight]
241.993 |
| Chemical Properties | Back Directory | [Boiling point ]
229.4±40.0 °C(Predicted) | [density ]
1.876±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [form ]
Solid | [pka]
7.61±0.10(Predicted) | [Appearance]
White to light brown Solid | [InChI]
InChI=1S/C6H3BrF3NO/c7-3-1-4(6(8,9)10)5(12)11-2-3/h1-2H,(H,11,12) | [InChIKey]
OPLCXLXORZDTMX-UHFFFAOYSA-N | [SMILES]
C1(=O)NC=C(Br)C=C1C(F)(F)F | [CAS DataBase Reference]
76041-79-7 |
| Hazard Information | Back Directory | [Synthesis]
Step 1: 3-(Trifluoromethyl)pyridin-2(1H)-one (25.0 g, 0.15 mol) was dissolved in acetic acid (300 mL) and sodium acetate (15.1 g, 0.18 mol) and bromine (8.6 mL, 0.17 mol) were added sequentially, dropwise. The reaction mixture was stirred at 80°C overnight. After completion of the reaction, the mixture was concentrated, diluted with saturated aqueous sodium bicarbonate and extracted twice with ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. Purification by column chromatography (petroleum ether/ethyl acetate = 7/2) afforded the target compound 5-bromo-3-(trifluoromethyl)pyridin-2(1H)-one (P45a) (29.7 g, 80% yield) as a white solid. | [References]
[1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 16, p. 6106 - 6122
[2] Patent: WO2012/139775, 2012, A1. Location in patent: Page/Page column 69-70
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6578 - 6581
[4] Patent: US2013/12491, 2013, A1. Location in patent: Paragraph 0171; 0172 |
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