2-Amino-3-hydroxypyridine Chemical Properties

Melting point:

168-172 °C (lit.)

Boiling point:

206.4°C (rough estimate)

Density 

1.2111 (rough estimate)

vapor pressure 

0.007-0.28Pa at 20-50℃

refractive index 

1.4800 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

5.15±0.10(Predicted)

form 

Crystalline Powder

color 

Grayish-beige to brownish

BRN 

109868

InChIKey

BMTSZVZQNMNPCT-UHFFFAOYSA-N

LogP

-0.25 at 23℃ and pH7.02-7.04

Surface tension

72.6mN/m at 1.053g/L and 20℃

CAS DataBase Reference

16867-03-1(CAS DataBase Reference)

NIST Chemistry Reference

2-Amino-3-hydroxypyridine(16867-03-1)

Safety Information

Hazard Codes 

Xi,T,Xn

Risk Statements 

36/37/38-25-40

Safety Statements 

26-45-37/39-28A-36-22

RIDADR 

UN2811

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333999

MSDS

• Language:English Provider:2-Amino-3-pyridinol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Amino-3-hydroxypyridine Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

2-Amino-3-hydroxypyridine was used as reagent in reaction of dimethyl acetylenedicarboxylate and triphenylphosphine to yield functionalized coumarins and 1,4-oxazines.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 14, p. 203, 1977 DOI: 10.1002/jhet.5570140206

General Description

2-Amino-3-hydroxypyridine forms complexes with number of transition metals. It inhibits the corrosion of aluminium and copper in acidic solutions. It undergoes condensation with 2-hydroxy-1-naphthaldehyde and 2-hydroxybenzaldehyde to form Schiffs bases. It is useful in the preparation of clinical anti-inflammatory analgesics.

Synthesis

General method: 3-hydroxy-2-nitropyridine (1 eq.), hexafluoroisopropanol (HFIP, 10 eq.) and iron powder (5 eq.) were added to the reaction tube and mixed. Subsequently, 2N aqueous hydrochloric acid solution was slowly added to the reaction mixture. The reaction mixture was stirred at room temperature for 30 minutes and then neutralized with saturated aqueous sodium bicarbonate (NaHCO3) solution. The organic layer was extracted three times with aqueous sodium bicarbonate and combined. The organic layers were subsequently washed with brine, dried over anhydrous sodium sulfate (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford the target product 2-amino-3-hydroxypyridine.

References

[1] Tetrahedron Letters, 2017, vol. 58, # 37, p. 3646 - 3649
[2] Journal of the Chemical Society, <1957> 4625,
[3] Pharmaceutical Bulletin, 1957, vol. 5, p. 350,352
[4] Biochemical Journal, 1950, vol. 46, p. 506
[5] Patent: US1889303, 1930,

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