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2-Amino-3-hydroxypyridine

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CAS:16867-03-1
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2-Amino-3-hydroxypyridine manufacturers

2-Amino-3-hydroxypyridine Basic information
Product Name:2-Amino-3-hydroxypyridine
Synonyms:2-Amino-3-hydroxypyridine Vetec(TM) reagent grade, 98%;2-AMINO-3-HYDROXYPYRIDINE;2-AMINO-3-PYRIDINOL;2-AMINO-3-PYRIDOL;2-AMINO-PYRIDIN-3-OL;2-amino-3-pyridi;3-HYDROXY-2-AMINOPYRIDINE;3-PYRIDINOL, 2-AMINO-
CAS:16867-03-1
MF:C5H6N2O
MW:110.11
EINECS:240-886-8
Product Categories:Building Blocks;C5;Chemical Synthesis;Heterocyclic Building Blocks;Amines;Aromatics;Pyridines derivates;Chemical Amines;Pyridines;Pyridine;pharmacetical;Pyridines, Pyrimidines, Purines and Pteredines
Mol File:16867-03-1.mol
2-Amino-3-hydroxypyridine Structure
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)
pka5.15±0.10(Predicted)
form Crystalline Powder
color Grayish-beige to brownish
BRN 109868
Cosmetics Ingredients FunctionsHAIR DYEING
Cosmetic Ingredient Review (CIR)2-Amino-3-hydroxypyridine (16867-03-1)
InChI1S/C5H6N2O/c6-5-4(8)2-1-3-7-5/h1-3,8H,(H2,6,7)
InChIKeyBMTSZVZQNMNPCT-UHFFFAOYSA-N
SMILESNc1ncccc1O
LogP-0.25 at 23℃ and pH7.02-7.04
Surface tension72.6mN/m at 1.053g/L and 20℃
CAS DataBase Reference16867-03-1(CAS DataBase Reference)
NIST Chemistry Reference2-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 Class6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard ClassificationsAcute Tox. 3 Oral
Eye Irrit. 2
Skin Irrit. 2
MSDS Information
ProviderLanguage
2-Amino-3-pyridinol English
SigmaAldrich English
ACROS English
ALFA English
2-Amino-3-hydroxypyridine Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powder
Uses2-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 Description2-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
3-Hydroxy-2-nitropyridine

15128-82-2

2-Amino-3-hydroxypyridine

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,
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