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4-Amino-2-hydroxy-5-methylpyridine

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4-Amino-2-hydroxy-5-methylpyridine Basic information

Product Name:
4-Amino-2-hydroxy-5-methylpyridine
Synonyms:
  • 4-amino-5-methylpyridine-2(1H)-one
  • 4-Amino-2-hydroxy-5-methylpyridine
  • 4-AMino-5-Methyl-2-(1H)-pyridinone
  • 4-AMino-5-Methylpyridin-2(1H)-one
  • 4-AMino-5-Methylpyridin-2-ol
  • 2(1H)-Pyridinone, 4-amino-5-methyl-
  • 4-amino-5-methyl-1H-pyridin-2-one
  • 4-amino-5-methylpyridone
CAS:
95306-64-2
MF:
C6H8N2O
MW:
124.14
EINECS:
682-818-3
Product Categories:
  • Intermediate
  • 95306-64-2
Mol File:
95306-64-2.mol
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4-Amino-2-hydroxy-5-methylpyridine Chemical Properties

Boiling point:
291.0±33.0℃ (760 Torr)
Density 
1.137±0.06 g/cm3 (20 ºC 760 Torr)
vapor pressure 
0-0Pa at 20-50℃
Flash point:
129.8±25.4℃
storage temp. 
2-8°C(protect from light)
pka
11.90±0.10(Predicted)
Appearance
White to off-white Solid
InChI
InChI=1S/C6H8N2O/c1-4-3-8-6(9)2-5(4)7/h2-3H,1H3,(H3,7,8,9)
InChIKey
SSQZBQXJYGNUSC-UHFFFAOYSA-N
SMILES
C1(=O)NC=C(C)C(N)=C1
LogP
-0.51 at 20℃ and pH6.3
CAS DataBase Reference
95306-64-2
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4-Amino-2-hydroxy-5-methylpyridine Usage And Synthesis

Description

4-Amino-2-hydroxy-5-methylpyridine belongs to the pyridine derivatives and is significantly alkaline. Its alcoholic hydroxyl group can undergo corresponding nucleophilic substitution reactions under alkaline conditions. It can be used as a material in organic synthesis and medicinal chemistry. The intermediate is used for the modification and production of drug molecules.

Chemical Properties

4-Amino-5-methyl-2-hydroxypyridine is insoluble in water and soluble in strong polar organic solvents. It has an amino group in its structure and therefore exhibits significant basicity. The carbonyl group in the structure can be considered to exist in an enolic form, and its alcoholic hydroxyl group can undergo the corresponding nucleophilic substitution reaction under basic conditions.

Uses

4-Amino-2-hydroxy-5-methylpyridine has been used as a reactant for the synthesis of finerenone, a selective mineralocorticoid receptor (MR) antagonist to be used to lower the risk of severe kidney and heart problems.

Synthesis

4-Amino-2-hydroxy-5-methylpyridine, dissolved in ethylene glycol, could be a starting material to synthesize 4-AMino-5-Methylpyridin-2-ol. The crude product could be precipitated by adding hydrochloric acid/methanol solution.

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