6-Methyl-2-pyridinecarboxaldehyde Chemical Properties

Melting point:

31-33 °C(lit.)

Boiling point:

105-108°C/12mm

Density 

1.1344 (rough estimate)

refractive index 

n20/D 1.527(lit.)

Flash point:

155 °F

storage temp. 

2-8°C

form 

Low Melting Solid

pka

3.96±0.10(Predicted)

color 

Light yellow to brown

Water Solubility 

750 g/L (20 ºC)

Sensitive 

Light Sensitive/Air Sensitive

BRN 

107476

InChIKey

AHISYUZBWDSPQL-UHFFFAOYSA-N

CAS DataBase Reference

1122-72-1(CAS DataBase Reference)

EPA Substance Registry System

6-Methyl-2-pyridinecarboxaldehyde (1122-72-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

RIDADR 

UN 1325

WGK Germany 

3

F 

8-9-23

TSCA 

Yes

HazardClass 

IRRITANT, LIGHT SENSITIVE, KEEP COLD

HS Code 

29339900

MSDS

• Language:English Provider:6-Methyl-2-pyridinecarboxaldehyde
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

6-Methyl-2-pyridinecarboxaldehyde Usage And Synthesis

Chemical Properties

light yellow to brown low melting solid

Uses

6-Methyl-2-pyridinecarboxaldehyde was used in the synthesis of 1-(10-cyano- and -10-bromo-5H-dibenzo[a,d]cyclohepten-5-yl)-4-[(arylmethylene)amino]piperazines which are compounds that exhibits anticon vulsant properties. 6-Methylpyridine-2-carboxaldehyde is used to produce 1-(6-methyl-pyridin-2-yl)-hexan-1-one with pent-1-ene at temperature of 100°C. This reaction will need reagent 2-amino-3-picoline and catalysts (Ph3P)3RhCl, Cp2ZrCl2.

Synthesis

Under stirring conditions, 10.47 g (0.081 mol) of selenite was dissolved in 30 mL of water and the resulting solution was slowly added to a 150 mL solution of 1,4-dioxane containing 20 g (0.162 mol) of 6-methyl-2-pyridinemethanol (3a). The reaction mixture was stirred continuously at 100 °C for 6 hours. Upon completion of the reaction, the resulting metallic selenium was removed by filtration. The filtrate was distilled under reduced pressure to remove the solvent and the residue was treated by extraction with hot hexane (3 x 150 mL). After combining the extracts, the solvents were again removed by distillation under reduced pressure and the resulting product did not require further purification. Finally, 14.76 g (0.121 mol, 75% yield) of 6-methyl-2-pyridinecarboxaldehyde was obtained with a melting point of 31-33 °C. The product structure was determined by 1H NMR. The structure of the product was determined by 1H NMR (DMSO-d6, δ, ppm): 2.61 (s, 3H, Me), 7.49 (d, 1H, 5-H, J = 7.5 Hz), 7.71 (d, 1H, 3-H, J = 7.5 Hz), 7.86 (dd, 1H, 4-H, J = 7.5, 7.5 Hz), 9.93 (s, 1H, CHO) and mass spectrum (m/z 122.06, I rel 100% [M + H]+) confirmed that the calculated molecular weight was 122.06.

References

[1] Tetrahedron Letters, 1999, vol. 40, # 9, p. 1635 - 1636
[2] Organometallics, 2016, vol. 35, # 10, p. 1505 - 1513
[3] Russian Journal of Organic Chemistry, 2017, vol. 53, # 7, p. 963 - 970
[4] Zh. Org. Khim., 2017, vol. 53, # 7, p. 951 - 958,8
[5] Dalton Transactions, 2012, vol. 41, # 22, p. 6661 - 6670

6-Methyl-2-pyridinecarboxaldehyde(1122-72-1)Related Product Information

• 6-METHYL-2-PYRIDINEMETHANOL
• 3-METHYL-2-PYRIDINECARBOXALDEHYDE
• Pyridoxal 5'-phosphate monohydrate
• Pyridoxal hydrochloride
• 2-Fluoro-6-methyl-5-pyridinecarboxaldehyde
• 3-Pyridinecarboxaldehyde,2,4-dimethyl-(9CI)
• 3-METHYL-4-PYRIDINECARBOXALDEHYDE
• 5-Methyl-3-pyridinecarboxaldehyde
• 2-(Aminomethyl)-3-pyridinecarboxaldehyde
• 3-BROMO-5-METHYL-4-PYRIDINECARBOXALDEHYDE
• 6-METHYL-3-PYRIDINECARBOXALDEHYDE
• 5-FLUORO-2-METHYL-3-PYRIDINECARBOXALDEHYDE
• Pyridoxal phosphate
• 5-(Aminomethyl)-3-pyridinecarboxaldehyde
• 3-FLUORO-6-METHYL-2-PYRIDINECARBOXALDEHYDE
• Pyridoxal 5’-Phosphate
• 2-(Aminomethyl)-4-pyridinecarboxaldehyde
• 2-METHYLISONICOTINALDEHYDE