2-Hydroxy-5-nitropyridine Chemical Properties

Melting point:

188-191 °C (lit.)

Boiling point:

256.56°C (rough estimate)

Density 

1.5657 (rough estimate)

refractive index 

1.4800 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Very Slightly)

form 

Crystalline Powder

pka

8.06±0.10(Predicted)

color 

Light yellow to beige

Water Solubility 

Soluble in hot water and alkali liquor, Insoluble in most of organic solvents.

BRN 

120352

InChI

InChI=1S/C5H4N2O3/c8-5-2-1-4(3-6-5)7(9)10/h1-3H,(H,6,8)

InChIKey

XKWSQIMYNVLGBO-UHFFFAOYSA-N

SMILES

C1(=O)NC=C([N+]([O-])=O)C=C1

CAS DataBase Reference

5418-51-9(CAS DataBase Reference)

NIST Chemistry Reference

2-Hydroxy-5-nitropyridine(5418-51-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:2-Hydroxy-5-nitropyridine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Hydroxy-5-nitropyridine Usage And Synthesis

Chemical Properties

light yellow to beige crystalline powder

Uses

A comparison of catalysts promotes imidazolide couplings including the identification of 2-hydroxy-5-nitropyridine as a new, safe, and effective catalyst.

Synthesis

General procedure for the synthesis of 2-hydroxy-5-nitropyridine from 2-amino-5-nitropyridine: 2-amino-5-nitropyridine (13.9 g, 0.1 mol) was dissolved in 55.6 g of 15% dilute hydrochloric acid, and 44.85 g of 20% aqueous sodium nitrite (NaNO2) was added slowly dropwise. After the dropwise addition, the reaction was continued for 6 hours. The reaction temperature was maintained at 40°C for 40 minutes. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and a light yellow solid was precipitated after cooling. The solid was washed with ice water and dried to obtain 2-hydroxy-5-nitropyridine (12.61 g), which was analyzed by high performance liquid chromatography (HPLC) with a purity of 97.69% and a yield of 88.02%.

References

[1] Patent: CN105523995, 2016, A. Location in patent: Paragraph 0026; 0047; 0048
[2] Chemistry of Heterocyclic Compounds, 2002, vol. 38, # 7, p. 805 - 809
[3] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 10, p. 3597 - 3602
[4] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1914, vol. 46, p. 1240
[5] Chem. Zentralbl., 1915, vol. 86, # I, p. 1066

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