2-Hydrazinopyridine Chemical Properties

Melting point:

41-44 °C (lit.)

Boiling point:

90-92 °C/1 mmHg (lit.)

Density 

1.1118 (rough estimate)

refractive index 

1.5340 (estimate)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

soluble in Methanol

pka

9.72±0.70(Predicted)

form 

crystalline

color 

deep red

BRN 

109984

InChIKey

NWELCUKYUCBVKK-UHFFFAOYSA-N

CAS DataBase Reference

4930-98-7(CAS DataBase Reference)

NIST Chemistry Reference

2-Hydrazinopyridine(4930-98-7)

EPA Substance Registry System

2-Hydrazinopyridine (4930-98-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

3-10-34

HS Code 

29339900

MSDS

• Language:English Provider:2-Pyridylhydrazine
• Language:English Provider:SigmaAldrich

2-Hydrazinopyridine Usage And Synthesis

Chemical Properties

White to light beige low melting solid

Synthesis Reference(s)

Journal of Medicinal Chemistry, 28, p. 1394, 1985 DOI: 10.1021/jm00148a004

Synthesis

General procedure for the synthesis of 2-hydrazinopyridine from 2-chloropyridine: To a solution of hydrazine hydrate (200 mL, 10 vol) of 2-chloropyridine (20 g, 0.176 mol, 1 eq.), the reaction was stirred for 48 hours at 100 °C. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding reagent ratio of 8:2 ethyl acetate and methanol), and after confirming that the feedstock was completely consumed, the reaction mixture was diluted with water (200 mL) and subsequently extracted with ethyl acetate (5 x 500 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure to remove the solvent to afford the target product 2-hydrazinopyridine (15.0 g, 78% yield) as a red oil. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 8.14 (1H, d, J = 3Hz, Ar-H), 7.51-7.45 (1H, m, Ar-H), 6.71-6.66 (2H, m, Ar-H), 5.78 (1H, brs, -NH), 3.81 (2H, brs, -NH2).LCMS ANALYSIS: The calculated value of C5H7N3[M+H]+ was 109.13 and the measured value was 110.1.

Purification Methods

Purify it by distillation under a vacuum and by recrystallisation from Et2O/hexane. [Kauffmann et al. Justus Liebigs Ann Chem 656 103 1962, Potts & Burton J Org Chem 31 251 1966.] The mono-hydrochloride has m 183o(dec) from aqueous HCl, and the di-hydrochloride has m 214-215o. [Beilstein 22 II 487, 22 III/IV 7025, 22/14 V 486.]

References

[1] Synthetic Communications, 2011, vol. 41, # 6, p. 925 - 938
[2] Asian Journal of Chemistry, 2017, vol. 29, # 9, p. 1920 - 1924
[3] European Journal of Organic Chemistry, 2015, vol. 2015, # 23, p. 5064 - 5069
[4] Patent: EP1380296, 2004, A1
[5] Tetrahedron Letters, 2014, vol. 55, # 52, p. 7198 - 7202

2-Hydrazinopyridine(4930-98-7)Related Product Information

• Chromium picolinate
• Pyridine
• 3-Aminopyridine
• tert-Butyl carbazate
• 4-Methylpyridine
• Carbobenzoxyhydrazide
• 2-Chloro-3-cyanopyridine
• Sulfasalazine
• Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate
• 2-Bromo-6-hydrazinopyridine
• PYRIDINE-2-CARBOXALDEHYDE 2-QUINOLYLHYDRAZONE
• 6-METHYL-4-(TRIFLUOROMETHYL)PYRID-2-YL HYDRAZINE
• 2-Hydrazinopyridine2HCl,2-HYDRAZINOPYRIDINE DIHYDROCHLORIDE,2-HYDRAZINOPYRIDINE HYDROCHLORIDE
• 1-[5-CHLORO-3-(TRIFLUOROMETHYL)-2-PYRIDYL]HYDRAZINE
• 3-HYDRAZINOPYRIDINE HYDROCHLORIDE
• 1-(2,3-Dimethylphenyl)piperazine
• 2-CHLORO-6-HYDRAZINOPYRIDINE
• 6-HYDRAZINO-1,3,4-TRIMETHYL-1H-PYRAZOLO[3,4-B]PYRIDINE