4-CHLOROPICOLINALDEHYDE Chemical Properties

Melting point:

32-34°

Boiling point:

206℃

Density 

1.332

Flash point:

79℃

storage temp. 

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

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

1.78±0.10(Predicted)

color 

Off-White to Pale Yellow

Stability:

Air Sensitive

Safety Information

Risk Statements 

43

Safety Statements 

36/37

HazardClass 

IRRITANT

HS Code 

2933399990

4-CHLOROPICOLINALDEHYDE Usage And Synthesis

Uses

4-Chloro-2-pyridinecarboxaldehyde is a useful synthetic intermediate. It is used in the synthesis of 2,2''-bipyridines, (chloropyridyl)(pyridyl)ethylamine and aryl and heteroaryl fluoromethyl ketones.

Synthesis

General procedure for the synthesis of 4-chloro-2-pyridinecarboxaldehyde from methyl 4-chloropyridinecarboxylate: to a solution of methyl 4-chloropyridinecarboxylate (2.5 g, 14.6 mmol) in anhydrous THF (100 mL) was added slowly and dropwise diisobutylaluminum hydride (1.0 M solution in THF, 29.1 mmol) at -78 °C and the reaction was stirred in an argon atmosphere at that temperature mixture for 2 hours. Upon completion of the reaction, the reaction was quenched with methanol (MeOH) at -78 °C, followed by the addition of potassium sodium tartrate solution (1.0 M, 180 mL), and the mixture was stirred and gradually warmed to room temperature over a period of 1 hour. The reaction mixture was diluted with ethyl acetate (EtOAc, 60 mL) and the organic layer was separated, washed with saturated saline and dried with anhydrous sodium sulfate. The solvent was removed by mild decompression distillation at room temperature to afford the target product 4-chloro-2-pyridinecarboxaldehyde (1.87 g, 91% yield), which solidified to light yellow crystals after standing at room temperature.

References

[1] Patent: US2004/186114, 2004, A1. Location in patent: Page/Page column 69; 70
[2] Patent: EP1897880, 2008, A1. Location in patent: Page/Page column 16
[3] Inorganic Chemistry, 2013, vol. 52, # 11, p. 6481 - 6501
[4] Bulletin of the Chemical Society of Japan, 2015, vol. 88, # 6, p. 784 - 791

4-CHLOROPICOLINALDEHYDE(63071-13-6)Related Product Information

• 4-CHLOROPYRIDINE-2,6-DICARBOHYDRAZIDE
• N-Methyl-4-chloropyridine-2-carboxamide
• dimethyl 4-chloropyridine-2,6-dicarboxylate
• 2-Chloro-3-pyridinecarboxaldehyde
• 4-CHLORO-PYRIDINE-2-CARBOXYLIC ACID HYDRAZIDE
• Tetrachloropyridine-2-carboxylic acid
• 3,4,5-Trichloropyridine-2-carboxylic acid
• 4-Chloropyridine-2-carboxamide
• 4-Chloropyridine-2-carboxylic acid
• 6-Chloropicolinaldehyde
• 2 6-DICHLOROPYRIDINE-3-CARBOXALDEHYDE
• 2-Chloroisonicotinaldehyde
• 2-Chloropyridine-5-carbaldehyde
• 2,3,5-Trichloropyridine-4-carboxaldehyde
• METHYL 3,4,5,6-TETRACHLOROPYRIDINE-2-CARBOXYLATE
• 3,4-DICHLOROPICOLINIC ACID
• 3,4,5-Trichloro-6-hydroxypyridine-2-carboxylic acid
• DIETHYL 4-CHLORO-2,6-PYRIDINEDICARBOXYLATE