3-METHYL-2-PYRIDINECARBOXALDEHYDE Chemical Properties

Melting point:

8°C(lit.)

Boiling point:

84°C/13mmHg(lit.)

Density 

1.080 g/mL at 25 °C

refractive index 

n20/D 1.538

Flash point:

74 °C

storage temp. 

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

pka

4.22±0.10(Predicted)

form 

Liquid

color 

Clear colorless to yellow

Water Solubility 

Slightly soluble in water.

CAS DataBase Reference

55589-47-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

3-METHYL-2-PYRIDINECARBOXALDEHYDE Usage And Synthesis

Uses

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.

Synthesis

General procedure for the synthesis of 3-methyl-2-pyridine aldehyde from (3-methylpyridin-2-yl)methanol: (3-methylpyridin-2-yl)methanol (1.9 mmol) was dissolved in 25 mL of 1,2-dichloroethane, 1.65 g (19 mmol) of activated manganese dioxide was added, and the reaction mixture was stirred for 6 hours at 50°C. The reaction was completed by filtration to remove the precipitate. After completion of the reaction, the precipitate was removed by filtration and the filtrate was evaporated under reduced pressure, the resulting residue was used directly in the next step of the reaction without further purification. 3-Methyl-2-pyridine aldehyde (1c) 185 mg (1.52 mmol, 80% yield) was obtained as a light oil.1H NMR (CDCl3) δ: 2.66 (s, 3H, Me), 7.39 (dd, 1H, 5-H, J = 7.8, 4.6 Hz), 7.62 (d, 1H, 4-H, J = 7.8 Hz), 8.66 ( d, 1H, 6-H, J = 4.6 Hz), 10.20 (s, 1H, CHO). Mass spectrum m/z: 122.06 (Irel 100%) [M+H]+. Calculated value: M 122.06.

References

[1] Russian Journal of Organic Chemistry, 2017, vol. 53, # 7, p. 963 - 970
[2] Zh. Org. Khim., 2017, vol. 53, # 7, p. 951 - 958,8
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1827 - 1837
[4] Patent: EP1431290, 2004, A1. Location in patent: Page 22
[5] Patent: EP1550657, 2005, A1. Location in patent: Page/Page column 64

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