6-Methylnicotinaldehyde Chemical Properties

Boiling point:

95℃/20mm

Density 

1.084

refractive index 

1.546

Flash point:

88℃

storage temp. 

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

pka

4.15±0.10(Predicted)

form 

Liquid

Appearance

Colorless to light yellow Liquid

Sensitive 

Moisture Sensitive

InChI

InChI=1S/C7H7NO/c1-6-2-3-7(5-9)4-8-6/h2-5H,1H3

InChIKey

IMWMEIWYPWVABQ-UHFFFAOYSA-N

SMILES

C1=NC(C)=CC=C1C=O

CAS DataBase Reference

53014-84-9

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36

Safety Statements 

26

WGK Germany 

3

HS Code 

29333990

6-Methylnicotinaldehyde Usage And Synthesis

Application

3-Aldehyde-6-methylpyridine is a pyridine heterocyclic compound mainly used in laboratory research and development of organic synthesis processes.

Synthesis

To a solution of 5-bromo-2-methylpyridine (151; 10 g, 58.1 mmol) in THF (150 mL) was added n-BuLi (2.5 M, 25.6 mL) at -78 ℃. The reaction mixture was stirred at this temperature for Ih. DMF (1.30 mL) was added,, and the resulting reaction mixture was stirred for 1 h at -78 °C. The addition of aq quenched the reaction. NH4Cl. Upon warming to room temperature, the mixture was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography to afford 6-methylnicotinaldehyde 152 (5.0 g, 72percent).

References

[1] Patent: US2006/287341, 2006, A1. Location in patent: Page/Page column 46
[2] Patent: US2007/4772, 2007, A1. Location in patent: Page/Page column 82
[3] Journal of Medicinal Chemistry, 1989, vol. 32, # 3, p. 583 - 593
[4] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
[5] Patent: US4778796, 1988, A

6-Methylnicotinaldehyde(53014-84-9)Related Product Information

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