5-IODO-3-(TRIFLUOROMETHYL)-2(1H)-PYRIDINONE Chemical Properties

Melting point:

145-147℃

Boiling point:

249℃

Density 

2.11

Flash point:

105℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

wooly crystalline powder

pka

7.80±0.10(Predicted)

color 

Light gold/orange

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

5-IODO-3-(TRIFLUOROMETHYL)-2(1H)-PYRIDINONE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-hydroxy-5-iodo-3-(trifluoromethyl)pyridine from 2-hydroxy-3-trifluoromethylpyridine: 1. 3-Trifluoromethyl-2-pyridinol (25 g, 153.3 mmol) was dissolved in a mixed solvent of anhydrous acetonitrile (150 mL) and N,N-dimethylformamide (150 mL). 2. N-iodosuccinimide (34.5 g, 153 mmol) was added to the above solution. 3. The reaction mixture was stirred at 80 °C for 2 hours and subsequently cooled to room temperature. 4. 1 M aqueous sodium bicarbonate (150 mL) was added to the cooled reaction mixture and stirred for 5 minutes. 5. The mixed solvents were evaporated to dryness, an appropriate amount of water was added and the aqueous phase was extracted twice with dichloromethane. 6. The organic phases were combined and evaporated, and the resulting crude product was recrystallized in water to give 36.2 g (81% yield) of a white powdery target product, 2-hydroxy-5-iodo-3-(trifluoromethyl)pyridine. Product characterization data: 1H NMR (500 MHz, CDCl3) δ 7.85 (d, J = 2.3 Hz, 1H), 7.98 (d, J = 2.3 Hz, 1H), 13.41 (br s, 1H). 13C NMR (250 MHz, CDCl3) δ 63.0, 121.4 (q, JC-F = 272.3 Hz), 122.2 (q, JC-F = 31.6 Hz), 144.4, 148.1 (q, JC-F = 5.0 Hz), 160.1.

References

[1] Organic Process Research and Development, 2013, vol. 17, # 12, p. 1561 - 1567
[2] Patent: WO2008/119015, 2008, A2. Location in patent: Page/Page column 48
[3] Patent: JP2016/11315, 2016, A. Location in patent: Paragraph 0084
[4] Patent: US9388159, 2016, B2. Location in patent: Page/Page column 19; 20; 21
[5] Patent: WO2015/100613, 2015, A1. Location in patent: Page/Page column 17

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