5-Hydroxynicotinic acid Chemical Properties

Melting point:

299 °C

Boiling point:

519.3±35.0 °C(Predicted)

Density 

1.485±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

2.08±0.10(Predicted)

form 

powder to crystal

color 

White to Yellow

BRN 

115847

InChI

InChI=1S/C6H5NO3/c8-5-1-4(6(9)10)2-7-3-5/h1-3,8H,(H,9,10)

InChIKey

ATTDCVLRGFEHEO-UHFFFAOYSA-N

SMILES

C1=NC=C(O)C=C1C(O)=O

CAS DataBase Reference

27828-71-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

QT1757500

Hazard Note 

Harmful/Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

29333990

5-Hydroxynicotinic acid Usage And Synthesis

Chemical Properties

White to off-white to yellow solid

Uses

5-Hydroxynicotinic acid is a nicotinic acid analog with potential inhibitory effect on the metabolism nicotinic acid by human platelets. Used in the investigation of the hydroxylation mechanism of the flaovoprotein 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase (MHPCO).

Definition

ChEBI: 5-Hydroxynicotinic acid is an aromatic carboxylic acid and a member of pyridines.

Synthesis

Stage A: Synthesis of 5-hydroxynicotinic acid 1. 10.1 g (0.05 mol) of 5-bromonicotinic acid, 10 g of NaOH (dissolved in 63 mL of water), 3.1 g of calcium sulfate pentahydrate, and 0.42 g of copper powder (0-valent) were added to a reaction flask. 2. The reaction mixture was stirred vigorously and heated under reflux conditions for 30 hours. 3. Upon completion of the reaction, the mixture was cooled to room temperature, 4.8 g Na2S-H2O was added and stirring was continued overnight. 4. The reaction mixture was heated to 70 °C and treated by passing H2S gas until the white precipitate completely disappeared (about 3 hours). 5. After cooling to room temperature, the reaction mixture was filtered. 6. Adjust the pH of the filtrate to 5.2 with concentrated hydrochloric acid and filter to collect the precipitate. 7. Adjust the pH of the filtrate again to 4.6 with concentrated hydrochloric acid and filter to collect the white precipitate. 8. 8. The precipitate was washed with water and dried under reduced pressure to give 4.3 g (yield: 62%) of 5-hydroxynicotinic acid (molecular formula: C7H5NO3). Product Characterization: - Appearance: white powder - Melting point: >260°C - 1H NMR (300 MHz, DMSO-d6) δ (ppm): 8.48 (d, J=1.5Hz, 1H), 8.26 (d, J=2.6Hz, 1H), 7.51 (d, J=1.9Hz, 1H) - IR (KBr, cm-1): 3273, 1538, 1393, 1294

Research

5-hydroxynicotinic acid (5HNA) could be used as a model the following questions were addressed: (i) is it possible to promote the crystallization of a tautomeric form dominant in a specific solvent through solvate formation? (ii) Does that form persist if the memory of solvation is erased through thermal desolvation?
A thermodynamic analysis based on DSC and Calvet drop microcalorimetry results allowed us to rationalize these observations, indicating that (i) 5HNA·H2O is predicted to spontaneously lose water, even for a relative humidity of 100%, hence its robustness is most certainly of kinetical origin; (ii) 5HNA·DMSO is thermodynamically stable when a saturation DMSO pressure can be established over the sample, but becomes unstable when exposed to an atmosphere where the solvent is absent. The kinetically easier desolvation of 5HNA·DMSO compared to 5HNA·H2O may be related to the fact that water is isolated in the crystal lattice (isolated site hydrate) while DMSO is placed in channels (channel solvate)[1].

References

[1] Joseph, Abhinav et al. “Tautomer selection through solvate formation: the case of 5-hydroxynicotinic acid?.” CrystEngComm 13 (2019): 2220–2233.

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