4-Hydroxy-3-nitropyridine Chemical Properties

Melting point:

285 °C (dec.) (lit.)

Boiling point:

382.1±22.0 °C(Predicted)

Density 

1.507±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

0.13±0.14(Predicted)

Appearance

White to light yellow Solid

BRN 

1072928

InChI

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

InChIKey

YUWOLBZMQDGRFV-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

5435-54-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-36/37/39-22

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

IRRITANT, IRRITANT-HARMFUL

HS Code 

29333990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Hydroxy-3-nitropyridine Usage And Synthesis

Chemical Properties

Light yellow crystalline powder

Uses

4-Hydroxy-3-nitropyridine may be used in the synthesis of 4-ethoxy-3-nitropyridine by treating with phosphorus pentachloride (PCl₅) followed by ethanol. It may also be used to prepare 4-chloro-3-nitropyridine by treating with PCl₅-POCl₃ (phosphorus oxychloride).

General Description

4-Hydroxy-3-nitropyridine can be synthesized by the nitration of 4-hydroxypyridine.

Synthesis

4-Hydroxypyridine (300 g, 3.15 mol, 1 wt) was added in batches to a 20 L flask containing concentrated sulfuric acid (1500 mL, 5 vol) under nitrogen protection. The nitration mixture was prepared by slowly adding concentrated nitric acid to concentrated sulfuric acid and under stirring. Subsequently, the nitrification mixture was cautiously transferred to a 20 L reactor. The reaction mixture was heated at 60°C to 70°C for 3 hours and subsequently cooled to room temperature over a period of 16 hours. The reaction mixture was poured into 10 L of ice water. The mixture was alkalized to pH 11-12 by dropwise addition of concentrated ammonia (8000 mL, 26.7 vol).The reaction mixture was concentrated under reduced pressure and the residue was stirred in pyridine (10000 mL, 33 vol) and filtered. The inorganic solid was dissolved in water (10000 mL, 33 vol) and extracted three times with pyridine (3 x 2500 mL, 3 x 8.3 vol), the pyridine extracts were combined and concentrated. The residue was stirred in acetone (6600 mL, 22 vol) for 1.5 h. It was filtered and dried over 16 h to give 716.1 g of crude product. The crude product, 4-hydroxy-3-nitropyridine (623.6 g), was slurried in water (1250 mL, 2 vol) for 60 min to remove residual inorganics. The slurry was filtered and dried for 72 h to give 4-hydroxy-3-nitropyridine (334.4 g, 76% yield, KF: 0.25%).1H NMR (400 MHz, DMSO): δ 6.58 (d, J = 6 Hz, 1H), 7.85 (d, J = 6 Hz, 1H), 8.88 (s, 1H).

References

[1] Organic Process Research and Development, 2004, vol. 8, # 6, p. 903 - 908
[2] Chemistry of Heterocyclic Compounds, 2012, vol. 48, # 8, p. 1235 - 1250
[3] Khim. Geterotsikl. Soedin., 2012, vol. 48, # 8, p. 1235 - 1250,16
[4] Journal of Materials Chemistry C, 2014, vol. 2, # 48, p. 10343 - 10356
[5] Heterocycles, 1999, vol. 51, # 4, p. 721 - 726

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