4-Chloropyridine-3-carboxaldehyde Chemical Properties

Boiling point:

228.8±20.0 °C(Predicted)

Density 

1.332±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

pka

1.89±0.10(Predicted)

form 

solid

color 

Pale yellow

InChI

InChI=1S/C6H4ClNO/c7-6-1-2-8-3-5(6)4-9/h1-4H

InChIKey

DYRMBQRXOMOMNW-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-43

Safety Statements 

26-36/37

HS Code 

2933399990

4-Chloropyridine-3-carboxaldehyde Usage And Synthesis

Chemical Properties

White to light yellow powder

Synthesis

General procedure: a tetrahydrofuran solution (50 ml) of 4-chloropyridine (25.0 g, 0.22 mol) was slowly added dropwise to a solution of diisopropylammonium lithium prepared from a hexane solution of 1.6 M n-butyllithium (179 ml, 0.29 mol) with diisopropylamine (33.4 g, 0.33 mol) in tetrahydrofuran (300 ml) under the protection of argon gas, keeping the reaction temperature at -78°C. After dropwise addition, stirring was continued for 30 min. Subsequently, N,N-dimethylformamide (DMF, 19.3 g, 0.26 mol) was added and the reaction mixture was gradually warmed up to room temperature. After completion of the reaction, extraction was carried out with ethyl acetate (200 ml) and 5% aqueous ammonium chloride solution (300 ml). The organic layer was separated, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent to give the crude product 4-chloro-3-pyridinecarboxaldehyde (27 g, 86% yield) as an oil. The product was characterized by 1H-NMR (200 MHz, CDCl3): δ 7.45 (1H, d, J = 5.0 Hz), 8.69 (1H, d, J = 5.0 Hz), 9.05 (1H, s), 10.51 (1H, s).

References

[1] Patent: EP1348706, 2003, A1. Location in patent: Page/Page column 37
[2] Patent: US2011/53975, 2011, A1. Location in patent: Page/Page column 60
[3] Journal of the American Chemical Society, 2013, vol. 135, # 40, p. 14916 - 14919
[4] Patent: WO2018/152329, 2018, A1. Location in patent: Page/Page column 44
[5] Patent: WO2004/41806, 2004, A2. Location in patent: Page 88-89

4-Chloropyridine-3-carboxaldehyde(114077-82-6)Related Product Information

• Chlorosulfonyl isocyanate
• Pentachloropyridine
• MCPA SODIUM
• N-Chlorosuccinimide
• 2-Chloro-5-chloromethylpyridine
• 3-Aminopyridine
• Clopidol
• 2-Chloro-3-cyanopyridine
• 3-Hydroxypyridine
• 4-Chloropyridinium chloride
• 4-CHLORO-1,3-DIMETHYLPYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLIC ACID
• 4-Chloronicotinic acid
• ETHYL 4-CHLORO-1,3-DIMETHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLATE
• 4-CHLORO-1,3-DIMETHYLPYRAZOLO[3,4-B]PYRIDINE-5-CARBONYL CHLORIDE
• 5-CHLORO-2-FORMYLPYRIDINE
• 5-Chloropyridine-3-carboxaldehyde
• 3-CHLOROPYRIDINE-4-CARBOXALDEHYDE
• 2-CHLOROPYRIDINE-3-CARBOXALDEHYDE,2-Chloropyridine-3-carboxaldehyde, 2-Chloro-3-formylpyridine