3-CHLOROISONICOTINALDEHYDE Chemical Properties

Melting point:

58-62 °C(lit.)

Boiling point:

93°C/6mmHg(lit.)

Density 

1.332±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

soluble in Methanol

pka

0.97±0.18(Predicted)

form 

Crystalline Powder

color 

White to yellow

Sensitive 

Air Sensitive

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/38-43-36/37/38

Safety Statements 

37/39-36-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

3-CHLOROISONICOTINALDEHYDE Usage And Synthesis

Chemical Properties

off-white to light yellow solid

Synthesis

The general procedure for the synthesis of 3-chloropyridine-4-carbaldehyde from 3-chloropyridine and N,N-dimethylformamide is as follows: 1. add toluene to a 250 mL round-bottomed flask and cool to -78°C. 2. LDA (11 mL, 22.02 mmol) was slowly added dropwise to a solution of 3-chloropyridine (8.80 mmol) in THF (20 mL) at -78°C and stirred at the same temperature for 1 to 2 hours. 3. DMF (822 μL, 10.56 mmol) was added, then the reaction mixture was brought to room temperature and stirred for 1 hour. 4. Ethyl acetate (EA) and water were added to the reaction mixture and the organic and aqueous layers were separated. 5. The organic solvent was further extracted with the aqueous phase and the organic extracts were combined. 6. The combined organic extracts were dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated in vacuum. 7. The crude product was purified by silica gel column chromatography to afford 3-chloropyridine-4-carbaldehyde (0.33 g, 30-65% yield). 8. The structure of the product was determined by NMR. 8. The structure of the product was confirmed by NMR (400 MHz, CDCl3): δ 7.73 (d, J = 8.0 Hz, 1H), 8.71 (d, J = 4.0 Hz, 1H), 8.81 (s, 1H), 10.52 (s, 1H).

References

[1] Heterocycles, 2006, vol. 67, # 2, p. 543 - 547
[2] Patent: WO2015/88271, 2015, A1. Location in patent: Page/Page column 208

3-CHLOROISONICOTINALDEHYDE(72990-37-5)Related Product Information

• 3-CHLOROISONICOTINALDEHYDE
• 2,5-Dichloroisonicotinic acid
• 2,3-DICHLOROPYRIDINE-4-CARBOXYLIC ACID
• 3,5-DICHLORO-4-FORMYL PYRIDINE
• 3-Chloroisonicotinic acid
• 2-BROMO-3,5-DICHLOROISONICOTINIC ACID
• 3-Chloropyridine-2-carboxaldehyde
• 2-Pyridinecarboxaldehyde, 3,6-dichloro-
• 2,3-Dichloropyridine-4-carboxaldehyde
• 2-Chloro-3-pyridinecarboxaldehyde
• 5-CHLORO-2-FORMYLPYRIDINE
• 5-CHLORO-PYRIDINE-3-CARBALDEHYDE
• 2-CHLOROISONICOTINALDEHYDE
• 4-Chloropyridine-3-carboxaldehyde
• 2,6-Dichloropyridine-4-carboxaldehyde
• 2,5-DICHLORO-4-FORMYLPYRIDINE
• 2-Chloropyridine-5-carbaldehyde
• 2,4-Dichloropyridine-3-carboxaldehyde