(5-CHLORO-PYRIDIN-2-YL)-HYDRAZINE Chemical Properties

Melting point:

127-128

Boiling point:

221.6±50.0 °C(Predicted)

Density 

1.43±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

form 

solid

pka

9.00±0.70(Predicted)

color 

Beige

InChI

InChI=1S/C5H6ClN3/c6-4-1-2-5(9-7)8-3-4/h1-3H,7H2,(H,8,9)

InChIKey

UXJYFOOFLZGBEK-UHFFFAOYSA-N

SMILES

C1(NN)=NC=C(Cl)C=C1

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933399990

(5-CHLORO-PYRIDIN-2-YL)-HYDRAZINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-chloro-2-hydrazinopyridine from 2,5-dichloropyridine: A mixed solution of 2,5-dichloropyridine (7.4 g, 50.0 mmol) and hydrazine hydrate (101 mL, 3250 mmol) in pyridine (100 mL) was heated and refluxed for 6 hours. Upon completion of the reaction, the reaction solution was concentrated to dryness in vacuum. The resulting residue was dissolved in dichloromethane (500 mL) and washed sequentially with 1N aqueous sodium hydroxide (500 mL) and water (3 x 500 mL). The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated to dryness in vacuo to afford 5-chloro-2-hydrazinopyridine (2.95 g, 20.55 mmol, 41% yield) as a light yellow solid.1H NMR (300 MHz, DMSO-d6) δ 7.97 (d, J = 2.5 Hz, 1H), 7.67 (s, 1H), 7.50 (dd, J = 9.0, 2.6 Hz, 1H), 6.73 (dd, J = 9.0, 0.6 Hz, 1H), 4.17 (s, 2H); MS (ES+) m/z 144.2 ([M+H]+).

References

[1] Journal of the American Chemical Society, 2011, vol. 133, # 17, p. 6780 - 6790
[2] Patent: US2003/187014, 2003, A1
[3] Patent: WO2015/134998, 2015, A1. Location in patent: Page/Page column 147
[4] Patent: US5750550, 1998, A
[5] Patent: US4997835, 1991, A

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