2-Amino-3-chloropyridine Chemical Properties

Melting point:

59-62℃

Boiling point:

207.0±20.0 °C(Predicted)

Density 

1.326±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

4.14±0.36(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C5H5ClN2/c6-4-2-1-3-8-5(4)7/h1-3H,(H2,7,8)

InChIKey

RZJPBQGRCNJYBU-UHFFFAOYSA-N

SMILES

C1(N)=NC=CC=C1Cl

CAS DataBase Reference

39620-04-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-37/38-22-20/21/22

Safety Statements 

26-36/37/39-39-36/37-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

2-Amino-3-chloropyridine Usage And Synthesis

Application

3-Chloro-2-aminopyridine belongs to the pyridine derivatives and is an intermediate in organic synthesis and pharmaceutical chemistry. Industrially, it can be used as a dyeing agent and in the synthesis of active pharmaceutical ingredients.

Chemical Properties

Light green solid

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 24, p. 1313, 1987 DOI: 10.1002/jhet.5570240516

Synthesis

The general procedure for the synthesis of 3-chloro-2-aminopyridine from 3-chloro-2-nitropyridine was as follows: 3-chloro-2-nitropyridine (1.00 g, 6.31 mmol) was dissolved in methanol (10 mL), and stannic(II) chloride (5.98 g, 31.54 mmol) and concentrated hydrochloric acid (2.63 mL, 31.54 mmol) were added sequentially. The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the reaction solution was diluted with ethyl acetate and washed with 1N NaOH solution. Subsequently, the organic phase was washed with saturated NaHCO3 solution and dried with anhydrous Na2SO4. Finally, the organic phase was concentrated under reduced pressure to afford the target product 3-chloro-2-aminopyridine (510.0 mg, 63% yield). The product was characterized by 1H NMR (400 MHz, CD3CN) with chemical shifts of δ 6.80 (m, 1H), 7.60 (d, 1H), 8.12 (d, 1H).

References

[1] Patent: WO2006/44775, 2006, A2. Location in patent: Page/Page column 64
[2] Patent: US2009/22670, 2009, A1. Location in patent: Page/Page column 25

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