2-CHLORO-5-IODO-3-(TRIFLUOROMETHYL)-PYRIDINONE Chemical Properties

Melting point:

43℃

Boiling point:

261℃

Density 

2.046

Flash point:

112℃

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

Solid

pka

-3.82±0.10(Predicted)

Water Solubility 

Slightly soluble in water.

Sensitive 

Light Sensitive

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

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

Uses

It is used as pharmaceutical intermediate and as an advanced chemical intermediate.

Synthesis

General procedure for the synthesis of 2-chloro-5-iodo-3-(trifluoromethyl)pyridine from 2-hydroxy-5-iodo-3-(trifluoromethyl)pyridine: In a microwave reaction vial, 5-iodo-3-trifluoromethyl-2-pyridinol (1 g, 3.47 mmol) was added to a pre-cooled mixture of POCl3 (1.60 mL) and DMF (1 mL). After sealing the vial, the reaction was heated at 110 °C for 20 min. Upon completion of the reaction, the mixture was cooled to room temperature and slowly poured into ice water. At this point, the product precipitated as a precipitate. The precipitate was collected by filtration, washed with cold water and dried to give 661 mg of the product in the form of a light brown powder in 62% yield. The structure of the product was determined by 1H NMR (500 MHz, CDCl3) δ 8.32 (d, J = 2.0 Hz, 1H), 8.81 (d, J = 2.0 Hz, 1H) and 13C NMR (250 MHz, CDCl3) δ 89.4, 121.2 (q, JC-F = 273.3 Hz), 126.8 (q, JC-F = 33.6 Hz), 144.34, 148.5, 158.7 for confirmation.

References

[1] Patent: WO2015/100613, 2015, A1. Location in patent: Page/Page column 17; 18
[2] Patent: WO2015/100617, 2015, A1. Location in patent: Page/Page column 36; 37
[3] Patent: WO2008/119015, 2008, A2. Location in patent: Page/Page column 48-49
[4] Patent: JP2016/11315, 2016, A. Location in patent: Paragraph 0084
[5] Patent: US9388159, 2016, B2. Location in patent: Page/Page column 20; 21

2-CHLORO-5-IODO-3-(TRIFLUOROMETHYL)-PYRIDINONE(887707-25-7)Related Product Information

• 3-IODO-1H-PYRIDIN-4-ONE
• 2-CHLORO-5-IODO-3-(TRIFLUOROMETHYL)-PYRIDINONE