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2-METHYL-4-HYDROXYMETHYLPYRIDINE

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2-METHYL-4-HYDROXYMETHYLPYRIDINE Basic information

Product Name:
2-METHYL-4-HYDROXYMETHYLPYRIDINE
Synonyms:
  • (2-methyl-4-pyridinyl)methanol
  • 2-METHYL-4-HYDROXYMETHYLPYRIDINE
  • 4-Pyridinemethanol,2-methyl-(9CI)
  • (2-Methylpyridin-4-yl)methanol
  • 4-(Hydroxymethyl)-2-methylpyridine
  • (2-Methylpyridin-4-yl)methanol, 4-(Hydroxymethyl)-2-picoline
  • (2-Methyl-4-pyridyl)methanol
  • 4-Pyridinemethanol, 2-methyl-
CAS:
105250-16-6
MF:
C7H9NO
MW:
123.15
Product Categories:
  • PYRIDINE
Mol File:
105250-16-6.mol
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2-METHYL-4-HYDROXYMETHYLPYRIDINE Chemical Properties

Boiling point:
131-140 °C(Press: 4 Torr)
Density 
1.092±0.06 g/cm3(Predicted)
storage temp. 
Inert atmosphere,Room Temperature
pka
13.46±0.10(Predicted)
form 
powder
color 
Pale yellow
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Safety Information

Hazard Codes 
Xn
Risk Statements 
20/21/22-36/37/38
Safety Statements 
26-36
HS Code 
2933399990
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2-METHYL-4-HYDROXYMETHYLPYRIDINE Usage And Synthesis

Synthesis Reference(s)

Synthesis, p. 483, 2002 DOI: 10.1055/s-2002-20960

Synthesis

152815-18-4

105250-16-6

General procedure for the synthesis of 2-methyl-4-hydroxymethylpyridine from (2-chloro-6-methylpyridin-4-yl)methanol: In a variant of the method described above, 2-chloro-6-methylpyridine-4-carboxylic acid, palladium catalyst (0.20 g, 10 mol% loaded on carbon), ethyl acetate (45 mL) and triethylamine (2.8 mL, 20 mmol) were mixed. The reaction mixture was placed under a hydrogen atmosphere at 1 atmosphere for 21 hours. Subsequently, additional Pearlman catalyst (0.2 g) was added and the reaction continued to be stirred for 5 hours under a hydrogen atmosphere to achieve dechlorination. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad and the filtrate was concentrated. Purification by column chromatography (eluent ratio 5:95 methanol:dichloromethane) afforded (2-methylpyridin-4-yl)methanol (1.48 g, 88% yield). The obtained (2-methylpyridin-4-yl)methanol can be used to prepare 2-amino-3-(2-methylpyridin-4-yl)propionitrile, and 1-methyl-1H-indol-2-one carboxylic acid ((1S,2R)-2-{[cyano -(2-methylpyridin-4-ylmethyl)-methyl]-carbamoyl}-cyclohexyl)amide obtained by the method described above (186 mg, yield 62%). Results of mass spectrometry analysis: m/z 444 (M+H).

References

[1] Patent: US2004/77646, 2004, A1. Location in patent: Page 116

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