3-BROMO-5-IODOPYRIDIN-2-AMINE Chemical Properties

Melting point:

106-110℃

Boiling point:

315.7±42.0 °C(Predicted)

Density 

2.426

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

2.15±0.49(Predicted)

Appearance

White to light yellow Solid

InChI

InChI=1S/C5H4BrIN2/c6-4-1-3(7)2-9-5(4)8/h1-2H,(H2,8,9)

InChIKey

OYZOHRSCEASBER-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(I)C=C1Br

Safety Information

HS Code 

2933399990

3-BROMO-5-IODOPYRIDIN-2-AMINE Usage And Synthesis

Synthesis

Step 1: Synthesis of 3-bromo-5-iodopyridin-2-amine N-bromosuccinimide (NBS, 20.2 g, 113 mmol) was slowly added to a stirred solution of 5-iodopyridin-2-amine (25.0 g, 113 mmol) in acetonitrile (500 mL) at room temperature. After the addition was completed, the reaction mixture continued to be stirred at room temperature for 72 hours. Subsequently, the reaction solution was concentrated under reduced pressure at 40 °C to remove the solvent. The resulting residue was purified by column chromatography (silica gel, 200-300 mesh, eluent ethyl acetate/petroleum ether, 3:1, v/v) to afford the target product 3-bromo-5-iodopyridin-2-amine (15.9 g, 47% yield) as a yellow solid. The product was identified by 1H NMR (300 MHz, DMSO-d6): δ 8.07 (s, 1H), 7.98-7.97 (m, 1H), 6.43 (brs, 2H, NH2).The LC/MS analysis showed the molecular ion peak [M+H]+ as 298.9.

References

[1] Journal of Medicinal Chemistry, 2004, vol. 47, # 10, p. 2453 - 2465
[2] Patent: US2012/309746, 2012, A1. Location in patent: Page/Page column 32
[3] Patent: WO2012/163724, 2012, A1. Location in patent: Page/Page column 51-52

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