2-Pyridinol-1-oxide Chemical Properties

Melting point:

147-152 °C

Boiling point:

387.7±15.0 °C(Predicted)

Density 

1.111

vapor pressure 

0.223Pa at 25℃

refractive index 

1.388

Flash point:

100 °C

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly)

form 

Solid

pka

pK1:-0.62;pK2:5.97(0) (25°C)

color 

Off-White to Light Yellow

Water Solubility 

331g/L

BRN 

1422545

InChI

1S/C5H5NO2/c7-5-3-1-2-4-6(5)8/h1-4,7H

InChIKey

JVHZMYAXZUIZKS-UHFFFAOYSA-N

SMILES

Oc1cccc[n+]1[O-]

LogP

-1.07 at 25℃

CAS DataBase Reference

13161-30-3(CAS DataBase Reference)

NIST Chemistry Reference

2-Pyridinol-1-oxide(13161-30-3)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-40

Safety Statements 

26-36-22

WGK Germany 

3

HS Code 

29333990

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich

2-Pyridinol-1-oxide Usage And Synthesis

Chemical Properties

Weight 20% solution in water

Uses

2-Pyridinol 1-oxide can be used:

• To fabricate gold electrodes for the electrochemical determination of europium using cyclic voltammetry.
• To prepare polymeric nickel (II) complex of 2-hydroxypyridine-N-oxide.
• In the synthesis of 1-methoxypyrid-4-one in the presence of sodium methoxide and methyl toluene-9-sulphonate.

Definition

Bactericidal agent related to aspergillic acid, made from pyridine-N-oxide.

General Description

2-Pyridinol 1-oxide (HOPO) is a peptide coupling agent used as a subsititue for HOBt. It can form stable chelate complexes with transition metal ions.

Synthesis

500L reactor add 2-chloropyridine 30 kg, 200 kg of tap water, sodium tungstate 1.5 kg, 2 kg of concentrated sulfuric acid, stirring to dissolve clear; temperature to 55 ??, slowly drop 30% hydrogen peroxide 100 kg; drop after the completion of the temperature to continue to react for 48 hours, HPLC test raw material conversion rate of 84%, cooled down to room temperature, add 12.3 kg of liquid alkali adjusted to neutral. Add toluene 50 kg, extract the raw material is not fully reacted (the layer can be concentrated to recover toluene and raw materials); aqueous layer to add 20 kg of sodium hydroxide, reflux reaction for 8 hours, HPLC monitoring, showing that the raw material is fully converted, cooled down to 25 ?? C, add hydrochloric acid to adjust the PH = 6, add ethyl acetate extraction, each time the dosage of 30 kg, extract three times, the combined organic phase, with anhydrous sodium sulfate 15 kg drying ; filter, concentrate the organic phase to 1/5 of the original volume, add 85 kg of 60-90 ?? C petroleum ether, cooled to -5 ?? C, stirring crystallization; filtration, drying, to obtain a light yellow crystal powder 22.9 kg, yield: 78.05% (calculated as 2-chloropyridine, and did not calculate the recovery of 2-chloropyridine).

References

[1] Laura Cruickshank. “Rare Elements Electrochemistry: The Development of a Novel Electrochemical Sensor for the Rapid Detection of Europium in Environmental Samples Using Gold Electrode Modified with 2-pyridinol-1-oxide.” Analytical Sciences 31 7 (2015): 623–627.

2-Pyridinol-1-oxide(13161-30-3)Related Product Information

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