4-Methoxy-3-pyridinecarboxaldehyde

4-Methoxy-3-pyridinecarboxaldehyde Property

Melting point:

63-67°C

Boiling point:

262.9±20.0 °C(Predicted)

Density 

1.159±0.06 g/cm3(Predicted)

storage temp. 

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

pka

4.75±0.18(Predicted)

Appearance

White to yellow Solid

CAS DataBase Reference

82257-15-6(CAS DataBase Reference)

Safety

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

HazardClass 

IRRITANT

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

H320Causes eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

4-Methoxy-3-pyridinecarboxaldehyde Chemical Properties,Usage,Production

Chemical Properties

light yellow solid

Uses

4-Methoxypyridine-3-carboxaldehyde, is an intermediate for the synthesis of 4-Hydroxy-3-pyridinecarboxylic Acid (H952780). It can also be used for the preparation of 7,8-dimethylquinolines derivatives as potential antimicrobial and antifungal agents.

Synthesis

Example 2 Preparation of 4-methoxypyridine-3-carbaldehyde To a stirred solution of tetrahydrofuran (380 mL) was added tert-butyllithium (90.6 mL, 154 mmol; 1.7 M in pentane) via cannula under nitrogen protection. The reaction mixture was cooled to -78°C, followed by dropwise addition of 2-bromotoluene (11.3 mL, 74.1 mmol). The reaction mixture was stirred at -78°C for 1 hour. Then, 4-methoxypyridine (5.79 mL, 57 mmol) was added dropwise to the reaction mixture at -78°C and the resulting mixture was stirred at -23°C for 3 hours. The reaction mixture was again cooled to -78°C, N,N-dimethylformamide (6.62 mL, 85.5 mmol) was added and stirring was continued at -78°C for 1 hour. The reaction mixture was slowly quenched with saturated aqueous sodium chloride solution (100 mL) at -78°C, followed by slow warming to room temperature. Ether (200 mL) was added to the reaction mixture and the organic and aqueous layers were separated. The aqueous layer was extracted with ether (2 x 150 mL) and the combined organic layers were dried with anhydrous potassium carbonate (20 g). The potassium carbonate was removed by filtration, the filter cake was washed with ether (100 mL), and the solvent was removed by concentration under reduced pressure. The resulting crude product, 4-methoxy-3-pyridinecarboxaldehyde, was purified by silica gel column chromatography (eluent ratio 5:95 ethanol:ethyl acetate) to afford 4.79 g of the target product as a yellow solid (61% yield; purity >98% as determined by 1H NMR).

References

[1] Tetrahedron Letters, 2006, vol. 47, # 1, p. 39 - 41
[2] Tetrahedron Letters, 2000, vol. 41, # 24, p. 4777 - 4780
[3] Patent: WO2005/42514, 2005, A2. Location in patent: Page/Page column 25
[4] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 419 - 434
[5] Journal of Organic Chemistry, 1990, vol. 55, # 1, p. 69 - 73