2-CHLORO-5-IODO-PYRIDIN-3-YLAMINE Chemical Properties

Melting point:

128-133°C

Boiling point:

352.5±42.0 °C(Predicted)

Density 

2.139±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

0.27±0.10(Predicted)

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26-39

WGK Germany 

3

HS Code 

2933399990

2-CHLORO-5-IODO-PYRIDIN-3-YLAMINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 3-amino-2-chloro-5-iodopyridine from 2-chloro-5-iodo-3-nitropyridine: 5-iodo-3-nitro-2-chloropyridine (230 mg, 0.809 mmol), ethanol (1 mL), water (6 drops), and concentrated hydrochloric acid (0.020 mL) were stirred at room temperature for 10 minutes. Subsequently, iron powder (500 mg, 8.95 mmol) was added in small portions and the reaction mixture was heated in an oil bath at 100 °C for 20 min. After completion of the reaction, the iron powder was removed by filtration and the filtrate was washed with ethanol. The ethanol layers were combined and concentrated under reduced pressure. The crude product was purified by fast chromatography using 9:1 hexane:ethyl acetate as eluent to afford 5-iodo-3-amino-2-chloropyridine (190 mg, 92% yield) as a colorless solid with a melting point of 129 °C. 1H NMR (CDCl3) δ (ppm): 4.15 (broad single peak, 2H), 7.34 (double peak, J = 2.0 Hz, 1H), and 7.96 (double peaks, J = 2.0 Hz, 1H); 13C NMR (CDCl3) δ (ppm): 91.41, 129.67, 136.31, 140.77, 143.90. Calculated values for elemental analysis (C5H4N2Cl): C, 23.60; H, 1.58; N, 11.01; Measured values: C, 23.66; H 1.52; N, 10.98.

References

[1] Journal of Organic Chemistry, 2011, vol. 76, # 23, p. 9841 - 9844
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 21, p. 4755 - 4761
[3] Patent: US6538010, 2003, B1
[4] Bioorganic & Medicinal Chemistry Letters, 2003, vol. 13, # 3, p. 525 - 528

2-CHLORO-5-IODO-PYRIDIN-3-YLAMINE(426463-09-4)Related Product Information

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