6-Methoxynicotinaldehyde Chemical Properties

Melting point:

51-54 °C (lit.)

Boiling point:

65-70 °C(Press: 12 Torr)

Density 

1.159±0.06 g/cm3(Predicted)

Flash point:

225 °F

storage temp. 

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

pka

1.60±0.10(Predicted)

form 

Crystalline Powder

color 

Off-white to light yellow

Water Solubility 

insoluble

InChI

InChI=1S/C7H7NO2/c1-10-7-3-2-6(5-9)4-8-7/h2-5H,1H3

InChIKey

CTAIEPPAOULMFY-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

65873-72-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

6-Methoxynicotinaldehyde Usage And Synthesis

Chemical Properties

off-white to light yellow crystalline powder

Uses

An intermediate for the synthesis of the somatostatic sst3 receptor.

Uses

Substrate used in a synthesis of flavanones via an L-proline-catalyzed condensation with o-hydroxyarylketones.

General Description

6-Methoxy-3-pyridinecarboxaldehyde, also known as 6-methoxy-3-nicotinaldehyde, can be prepared from 5-bromo-2-methoxypyridine.

Synthesis

At -78 °C, N-butyllithium (50 mL, 2.5 M hexane solution) was slowly added dropwise to a solution of 5-bromo-2-methoxypyridine (22.4 g, 119.1 mmol) in anhydrous tetrahydrofuran (240 mL). After the dropwise addition, the reaction mixture was continued to be stirred at -78 °C for 90 min. Subsequently, N,N-dimethylformamide (18.5 mL, 238.3 mmol) was added slowly dropwise and stirring was continued for 90 min at -78 °C. Upon completion of the reaction, the mixture was slowly warmed to room temperature. The reaction mixture was poured into saturated sodium bicarbonate solution (1000 mL) and extracted with ether (3 x 250 mL). The organic phases were combined, dried with magnesium sulfate, filtered and concentrated to dryness to give 15.4 g (94% yield) of 6-methoxy-3-pyridinecarboxaldehyde as a light yellow solid. The product was characterized by 1H NMR (DMSO-d6): δ= 9.97 (s, 1H), 8.77 (m, 1H), 8.12 (dd, 1H, J = 8.6, 2.3 Hz), 6.99 (d, 1H, J = 8.7 Hz), 3.97 (s, 3H).LC/MS analysis (Method A): retention time = 0.25 min, purity = 92.8%, calculated mass = 137, [M + H]+ = 138. HPLC analysis (Method C): retention time = 4.9 min, purity = 95.9% (210-370 nm) and 98.7% (256 nm).

References

[1] Synthesis, 2012, vol. 44, # 5, p. 735 - 746
[2] Journal of medicinal chemistry, 2004, vol. 47, # 20, p. 4829 - 4837
[3] Patent: US2006/19965, 2006, A1. Location in patent: Page/Page column 27
[4] Synthesis, 1994, # 1, p. 87 - 92
[5] Synlett, 2009, # 15, p. 2508 - 2512

6-Methoxynicotinaldehyde(65873-72-5)Related Product Information

• 3-Pyridinecarboxaldehyde
• Anisole
• 2-Methoxypyridine
• 5-Bromo-2-methoxypyridine
• 5-Amino-2-methoxypyridine
• o-Anisaldehyde
• 4-Methoxybenzylchloride
• 6-methoxybenzofuran-2-ylboronic acid
• 6-METHOXYPYRIDINE-2-CARBOXYLIC ACID
• 4-Methoxyphenylacetone
• p-Anisaldehyde
• 2-Methoxy-5-nitropyridine
• p-Anisidine
• (Trifluoromethoxy)benzene
• 3-(METHOXYMETHOXY)BENZALDEHYDE
• 2-Methoxy-5-fluoropyridine
• 2,6-Dimethoxypyridine-3-carboxylic acid
• 5-METHOXY-3-PYRIDINECARBOXALDEHYDE,3-METHOXY-5-PYRIDINECARBOXALDEHYDE,5-METHOXYNICOTINALDEHYDE