2-Pyridinemethanol,5-chloro-(9CI) Chemical Properties

Melting point:

45～47℃

Boiling point:

234.9±25.0 °C(Predicted)

Density 

1.324±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

13.12±0.10(Predicted)

color 

Grey

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

2-Pyridinemethanol,5-chloro-(9CI) Usage And Synthesis

Synthesis

General procedure for the synthesis of (5-chloro-2-pyridyl)methanol from methyl 5-chloropyridine-2-carboxylate: 1. Synthesis of intermediate 2: (5-chloro-2-pyridyl)methanol - Methyl 5-chloro-2-pyridinecarboxylate (43 g, 251 mmol) was dissolved in methanol (400 mL) at 0 °C. - NaBH4 (28.7 g, 754 mmol) was added to the above solution in small portions over about 30 min. - After addition, the reaction mixture was stirred at room temperature for 2 h. The completion of the reaction was confirmed by TLC analysis. - After completion of the reaction, the mixture was concentrated under reduced pressure and the residue was adjusted to pH 1 with 1N HCl. - The resulting solution was extracted with EtOAc (3 x 300 mL) and the organic layers were combined. - The organic layer was dried with Na2SO4 and the solvent was evaporated. - The residue was purified by silica gel column chromatography using 10:1 petroleum ether/EtOAc as eluent to afford the title compound (5-chloro-2-pyridyl)methanol (36 g, 99%). Product Characterization: 1H NMR (1H NMR). - Product characterization: 1H NMR (400 MHz, CDCl3) δ ppm 8.44 (d, J = 1.60 Hz, 1H), 7.62 (dd, J = 8.40, 2.40 Hz, 1H), 7.25 (d, J = 8.40 Hz, 1H), 4.69 (s, 2H), 3.83 (s, 1H).

References

[1] Patent: WO2009/76387, 2009, A1. Location in patent: Page/Page column 27
[2] Patent: WO2010/141538, 2010, A1. Location in patent: Page/Page column 18-19
[3] Patent: WO2010/141539, 2010, A1. Location in patent: Page/Page column 18-19
[4] Patent: WO2010/141545, 2010, A1. Location in patent: Page/Page column 19-20
[5] Patent: WO2010/141540, 2010, A1. Location in patent: Page/Page column 17-18

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