| Identification | More | [Name]
2-Hydrazinopyridine | [CAS]
4930-98-7 | [Synonyms]
2-HYDRAZINOPYRIDINE
2-PYRIDYLHYDRAZINE
PYRIDIN-2-YL-HYDRAZINE
(2E)-2(1H)-Pyridinone hydrazone
2(1H)-Pyridinone, hydrazone
2(1h)-pyridinone,hydrazone
Hydrazine, 2-pyridinyl-
Pyridine, 2-hydrazino-
Hydrazinopyridine
2-hydrazinylpyridine
2-HYDRAZINOPYRIDINE 97+%
2-HYDRAZINOPYRIDINE PYRIDIN-2-YL-HYDRAZINE
2-Pyridinylhydrazine | [EINECS(EC#)]
225-566-8 | [Molecular Formula]
C5H7N3 | [MDL Number]
MFCD00006249 | [Molecular Weight]
109.13 | [MOL File]
4930-98-7.mol |
| Chemical Properties | Back Directory | [Appearance]
White to light beige low melting solid | [Melting point ]
41-44 °C (lit.) | [Boiling point ]
90-92 °C/1 mmHg (lit.) | [density ]
1.1118 (rough estimate) | [refractive index ]
1.5340 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
soluble in Methanol | [form ]
crystalline
| [pka]
9.72±0.70(Predicted) | [color ]
deep red
| [Detection Methods]
GC | [BRN ]
109984 | [InChIKey]
NWELCUKYUCBVKK-UHFFFAOYSA-N | [CAS DataBase Reference]
4930-98-7(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Hydrazinopyridine(4930-98-7) | [Storage Precautions]
Store under nitrogen | [EPA Substance Registry System]
4930-98-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
3-10-34 | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [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 |
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