2-CHLORO-5-(TRIFLUOROMETHYL)-3-PYRIDINAMINE Chemical Properties

Boiling point:

256.8±40.0 °C(Predicted)

Density 

1.507±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-0.29±0.10(Predicted)

form 

Solid

color 

Off-white to brown

Water Solubility 

Slightly soluble in water.

CAS DataBase Reference

72587-18-9

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

2-CHLORO-5-(TRIFLUOROMETHYL)-3-PYRIDINAMINE Usage And Synthesis

Uses

It's employed as a intermediate for pharmaceutical.

Synthesis

The general procedure for the synthesis of 3-amino-2-chloro-5-(trifluoromethyl)pyridine from 5-(trifluoromethyl)-3-nitro-2-chloropyridine was as follows: zinc(II) dichloride dihydrate (4.39 g, 19.5 mmol) was added to 2-chloro-3-nitro-5-(trifluoromethyl)pyridine (1.00 g, 4.41 mmol) in ethyl acetate (25 mL) solution. The resulting suspension was stirred at 80°C for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature and then slowly added dropwise to an ice-cooled saturated sodium bicarbonate solution (100 mL). After the temperature was brought to room temperature, the product was separated. The suspension was filtered through a diatomaceous earth layer and the residue was washed four times with ethyl acetate (50 mL each time). The filtrate and washings were combined and washed sequentially with saturated sodium bicarbonate solution, water and saturated aqueous sodium chloride solution. The organic phase was dried over magnesium sulfate, filtered and concentrated to dryness. Yield: 0.78 g (90%). 1H-NMR (CD2Cl2, 400 MHz) data were as follows: δ=4.4 (br s, 2H), 7.24 (d, 1H), 8.02 (d, 1H).

References

[1] Patent: US2012/319050, 2012, A1. Location in patent: Page/Page column 64-65
[2] Patent: WO2012/172482, 2012, A1. Location in patent: Page/Page column 126
[3] Patent: WO2017/133657, 2017, A1. Location in patent: Page/Page column 64
[4] Patent: WO2017/133667, 2017, A1. Location in patent: Page/Page column 175; 176

2-CHLORO-5-(TRIFLUOROMETHYL)-3-PYRIDINAMINE(72587-18-9)Related Product Information

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