6-Hydroxy-5-nitronicotinic acid Chemical Properties

Melting point:

269-271

Boiling point:

363.6±42.0 °C(Predicted)

Density 

1.70±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

3.09±0.50(Predicted)

color 

Light yellow to Yellow

BRN 

177986

InChI

InChI=1S/C6H4N2O5/c9-5-4(8(12)13)1-3(2-7-5)6(10)11/h1-2H,(H,7,9)(H,10,11)

InChIKey

VJMXJGVEVASJOD-UHFFFAOYSA-N

SMILES

C1NC(=O)C([N+]([O-])=O)=CC=1C(O)=O

CAS DataBase Reference

6635-31-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37

Safety Statements 

26

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

2933399990

6-Hydroxy-5-nitronicotinic acid Usage And Synthesis

Uses

6-Hydroxy-5-nitronicotinic acid is mainly used as an antibacterial agent and pharmaceutical intermediate.

Chemical Reactivity

6-Hydroxy-5-nitronicotinic acid is stable under proper conditions, it reacts with oxidizing agents.

Synthesis

6-Hydroxy-5-nitronicotinic acid is synthesised using 6-Hydroxynicotinic acid as a raw material by chemical reaction. The specific synthesis steps are as follows:
6-Hydroxynicotinic acid 2 (25.0 g, 180 mmol) was dissolved in HNO3 fuming (1.52) (95 mL) and stirred at 50 oC for 18 h. After the solution was cooled to room temperature, the mixture was concentrated, and then co-evaporated with water, followed by the addition of MeOH to afford a brown precipitate. The precipitate was filtered and washed with 50 mL of cold MeOH twice. After drying under reduced pressure, a brown color product 3 was obtained; yield: 9.67 g (29percent); 1H NMR (300 MHz, CD3OD) 8.44 (d, J = 2.6 Hz, 1H), 8.85 (d, J = 2.6 Hz, 1H) ; HRMS (ES+): m/z 185.0194 (M+H+) (calcd for C6H5N2O5: 185.0198).

References

[1] Tetrahedron Letters, 1999, vol. 40, # 12, p. 2227 - 2230
[2] Tetrahedron Letters, 2012, vol. 53, # 5, p. 535 - 538
[3] Patent: WO2016/138335, 2016, A1. Location in patent: Paragraph 00372
[4] Journal of the American Chemical Society, 1956, vol. 78, p. 423
[5] Journal of the Chemical Society, 1951, p. 2590,2593

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