6-CHLORO-4-IODOPYRIDIN-3-AMINE Chemical Properties

Boiling point:

359.4±42.0 °C(Predicted)

Density 

2.139±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

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

pka

0.60±0.10(Predicted)

form 

crystalline powder

color 

Faint yellow

InChI

InChI=1S/C5H4ClIN2/c6-5-1-3(7)4(8)2-9-5/h1-2H,8H2

InChIKey

UOICMMKVFPTQMX-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=CC(I)=C1N

Safety Information

HS Code 

2933399990

6-CHLORO-4-IODOPYRIDIN-3-AMINE Usage And Synthesis

Synthesis

Step c: Synthesis of 6-chloro-4-iodo-pyridin-3-amine Tert-butyl (6-chloro-4-iodo-pyridin-3-yl)-carbamate (10.0 g, 28 mmol) was dissolved in 3 M hydrochloric acid (600 mL), heated to 60°C, and reacted for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted with saturated sodium bicarbonate solution to 8. Subsequently, the aqueous layer was extracted with ethyl acetate (100 mL × 3). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent being a petroleum ether solution of 10% ethyl acetate to give 6-chloro-4-iodopyridin-3-amine (6.6 g, 93% yield). 1H-NMR (CDCl3, 400 MHz) δ 7.81 (s, 1H), 7.60 (s, 1H), 4.13 (br s, 2H).

References

[1] Patent: US2009/253736, 2009, A1. Location in patent: Page/Page column 29
[2] Patent: WO2009/151598, 2009, A1. Location in patent: Page/Page column 122-123
[3] Patent: US2002/22624, 2002, A1
[4] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 9, p. 1233 - 1236
[5] Patent: WO2006/59164, 2006, A2. Location in patent: Page/Page column 22