(5-CYANOPYRIDIN-3-YL)-METHANOL Chemical Properties

Boiling point:

315.0±27.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

13.26±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C7H6N2O/c8-2-6-1-7(5-10)4-9-3-6/h1,3-4,10H,5H2

InChIKey

MNMDVGJZONSKMO-UHFFFAOYSA-N

SMILES

C1=NC=C(CO)C=C1C#N

CAS DataBase Reference

135124-71-9

Safety Information

RIDADR 

UN1759

(5-CYANOPYRIDIN-3-YL)-METHANOL Usage And Synthesis

Application

(5-Cyanopyridin-3-yl)-methanol is a pharmaceutical intermediate that can be prepared from 5-bromonicotinonitrile through a three-step reaction and can be used in laboratory research and development processes and chemical production processes.

Synthesis

Add lithium aluminum hydride (1.0M in THF; 1.5mL, 1.5mmol, 0.5equiv) over a period of 3 min to a solution of 5-cyano-nicotinic acid methyl ester (479mg, 2.95mmol, 1 equiv) in anhydr THF (15mL) and cool to -78°C After 1h while still at -78°C, quench the reaction with H2O (60μL), 5M aq NaOH (60μL), and more H2O (180μL). Filter the reaction mixture through paper. Rotary evaporate the filtrate (40°C) to give 369mg of material as a yellow solid. Transfer this material to a column of silica gel (130mm x 25mmdia.) and elute (2% MeOH/CH2Cl2) to yield 180mg of a mixture of ester, hemiacetal, and aldehyde as a yellow solid and 45mg (11%) of 5-hydroxymethyl-nicotinonitrile as a yellow solid. MS (m/e): 163.07 (M+1).

References

[1] Patent: US2018/65917, 2018, A1. Location in patent: Paragraph 0377

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