ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Hydroxypyridine 2-Amino-3-hydroxypyridine

2-Amino-3-hydroxypyridine

Product Name2-Amino-3-hydroxypyridine
CAS16867-03-1
MFC5H6N2O
MW110.11
EINECS240-886-8
MOL File16867-03-1.mol

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
Cosmetics Ingredients Functions	HAIR DYEING
Cosmetic Ingredient Review (CIR)	2-Amino-3-hydroxypyridine (16867-03-1)
InChI	1S/C5H6N2O/c6-5-4(8)2-1-3-7-5/h1-3,8H,(H2,6,7)
InChIKey	BMTSZVZQNMNPCT-UHFFFAOYSA-N
SMILES	Nc1ncccc1O
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
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral Eye Irrit. 2 Skin Irrit. 2

MSDS

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

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

15128-82-2

16867-03-1

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,

2-Amino-3-hydroxypyridine

Chemical Properties

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MSDS

Usage And Synthesis

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