2,4-DICHLORO-3-AMINOPYRIDINE Chemical Properties

Boiling point:

265℃

Density 

1.497

Flash point:

114℃

storage temp. 

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

pka

0.72±0.10(Predicted)

Appearance

Light yellow to brown Solid

InChI

InChI=1S/C5H4Cl2N2/c6-3-1-2-9-5(7)4(3)8/h1-2H,8H2

InChIKey

ZSJYSZWQVCWDQO-UHFFFAOYSA-N

SMILES

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

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

2,4-DICHLORO-3-AMINOPYRIDINE Usage And Synthesis

Chemical Properties

2,4-dichloro-3-aminopyridine is a white crystalline solid with a distinctive odor. It has good solubility, soluble in alcohol and ether organic solvents.

Uses

2,4-dichloro-3-aminopyridine is widely used in the field of organic synthesis. It has many important uses in the pharmaceutical, pesticide industries. 

Synthesis

2,4-Dichloro-3-nitropyridine (2.058 g, 10 mmol) was dissolved in acetic acid (10 mL) under nitrogen protection. Iron powder (1.9191 g, 34.4 mmol) was subsequently added. The reaction mixture was heated and stirred at 40 °C for 2 hours. After completion of the reaction, the mixture was poured into ice water and adjusted to neutral with sodium bicarbonate. The reaction mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic phases were washed once with saturated sodium bicarbonate solution (1 x 100 mL). The aqueous layer was back-extracted once more with ethyl acetate (100 mL). All organic phases were combined, dried with magnesium sulfate, filtered and concentrated under reduced pressure to give 3-amino-2,4-dichloropyridine (1.510 g, 9.26 mmol, 87% yield).

References

[1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 3, p. 1511 - 1530
[2] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4288 - 4312
[3] Patent: WO2007/106192, 2007, A2. Location in patent: Page/Page column 67
[4] Patent: WO2008/134679, 2008, A1. Location in patent: Page/Page column 90-91
[5] MedChemComm, 2016, vol. 7, # 5, p. 1022 - 1032

2,4-DICHLORO-3-AMINOPYRIDINE(173772-63-9)Related Product Information

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